The 37 Best New England Day Trips by Season (2025)

New England may be small compared to other regions in the U.S., but there are endless places to visit. I’ve lived here for almost five years and still feel like I’ve only scratched the surface of all there is to see and do.

The six states that make up this region — Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont — offer a beautiful blend of coastal landscapes, picturesque countryside, and vibrant urban centers.

After traveling extensively in this stunning corner of the country, I’ve compiled this list of the 37 best day trips in New England.

⏰ Short on time?
Here are my top four New England day trip recommendations:

☀️ Summer Top Pick: Ogunquit, Maine

Best Things to Do in Ogunquit:

Soak up the sun on Ogunquit Beach
Browse the shops at Perkins Cove
Hike Marginal Way
Walk along Main Street
Eat seafood at Ogunquit Beach Lobster House

Best Hotels if You Want to Extend Your Stay:

📍Ogunquit River Inn & Suites
📍The Grand Hotel

🍁 Fall Top Pick: Acadia National Park, Maine

Best Things to Do in Acadia:

Drive or hike to the summit of Cadillac Mountain
Hike the Ocean Path Trail and relax on Sand Beach
Hike around Jordan’s Pond and order popovers at Jordan’s Pond House Restaurant
Drive the scenic Park Loop Road
Visit the nearby town of Bar Harbor

Best Hotels if You Want to Extend Your Stay:

📍The Inn on Mount Desert
📍Bar Harbor Grand Hotel

❄️ Winter Top Pick: Stowe, Vermont

Best Things to Do in Stowe:

Ski at Stowe Mountain Resort or Smugglers’ Notch Resort
Explore the shops and galleries in downtown Stowe
Hike or snowshoe along the Stowe Recreation Path

Best Hotels if You Want to Extend Your Stay:

📍Trapp Family Lodge
📍Stowe Village Inn

🌸 Spring Top Pick: Boston, Massachusetts

Best Things to Do in Boston:

Tour the Freedom Trail
Visit the Boston Tea Party Ships & Museum
Go on a Duck Boat Tour
Explore the Public Garden and Boston Common
Stroll along Newbury Street and the Charles River Esplanade
Take a walk down Charles Street in Beacon Hill

Best Hotels if You Want to Extend Your Stay:

📍Hyatt Regency Boston Harbor
📍Omni Parker House

Best Day Trips in New England in the Summer

New England summers are fantastic. Since most of the states have their own coastline, it’s no surprise that many of the top places to visit in the summer are near the water. But I’ve included a couple of amazing inland destinations as well!

Here are my favorite summer day trip destinations in New England:

1. Ogunquit, Maine

Best as a day trip from Boston, MA; Portland, ME; Manchester, NH

I had never heard of Ogunquit until my husband surprised me with a birthday trip there one year, and this coastal town quickly became one of my favorite places in New England.

Start your day with some fun in the sun at Ogunquit Beach, the largest and most popular beach in town. The beach sits on a small strip of land separated from the mainland by a small saltwater river. People often sit on the riverside to enjoy the calm water (especially great if you have small kiddos!).

Stop for seafood at the Ogunquit Beach Lobster House before walking to Main Street to browse the many shops and cafes lined on either side.

Be sure to also visit Perkins Cove, a cluster of quaint shops and restaurants nestled along Ogunquit Harbor. From there, you’ll find the entrance to Marginal Way, a 1.25-mile trail that stretches along the coast and provides stunning views of the ocean the entire way.

2. Portland, Maine

Best as a day trip from Boston, MA; Bangor, ME; Portsmouth, NH

Pay a visit to Maine’s largest city, Portland. Also located on the Atlantic Ocean, Portland is an eclectic city with both a rich New England heritage and artsy, hipster vibes.

Here you will find one of New England’s smallest lighthouses, Bug Light, which is only 26 feet tall. From there, walk along the beautiful Eastern Promenade for incredible views of Casco Bay.

Experience what it was like to ride a train in the 1800s and early 1900s by purchasing tickets for the historic Maine Narrow Gauge Railroad. Then fill up on fresh seafood from the Portland Farmer’s Market (open Wednesdays and Saturdays) or Harbor Fish Market.

You also can’t miss making the quick drive over to Cape Elizabeth to see Portland Head Light, America’s most photographed lighthouse. This is one of the most breathtaking places I have seen in all of New England.

3. Portsmouth, New Hampshire

Best as a day trip from Boston, MA; Portland, ME; Manchester, NH

Situated along the Piscataqua River and just a couple miles from the Atlantic Ocean, Portsmouth is another historic city with a rich maritime heritage.

Wander the cobblestone streets and browse through the numerous boutiques, art galleries, and cafes of Market Square.

Stop for brunch at the original The Friendly Toast restaurant, known for its eclectic and colorful interior and expansive menu. I love their Eggs Benedict and French Toast!

The Flatbread Company is another local favorite where you can enjoy delicious flatbread pizza made with locally sourced ingredients.

Take a walk along the Portsmouth Harbor Trail and admire the views at Prescott Park, located right on the water.

When in Portsmouth, it’s also worth a quick drive down the coast to Rye Beach and Jenness Beach if you’re craving some fun in the sand and sun.

New England Day Trip: Gloucester, Massachusetts

4. Gloucester, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Portland, ME; Portsmouth, NH

When I first moved to Boston, locals recommended I check out Gloucester for the perfect beach day. They weren’t wrong! This lively town on Cape Ann exudes traditional New England coastal vibes and is one of the best places to spend a warm summer day.

Two of the most popular beaches in Gloucester are Good Harbor Beach and Wingaersheek Beach. I loved Good Harbor Beach for its soft sand and rocky coastline views. There’s also an island not far from the coast called Little Salt Island that you can walk to during low tide!

Another exciting option for your day in Gloucester is going on a whale-watching tour. Take a four-hour cruise to the Stellwagen Bank National Marine Sanctuary to see a variety of whales and dolphins.

🐳 Book Your Gloucester Whale-Watching Tour

While in town, grab a scoop or two (why not three?) from Holy Cow Ice Cream Cafe. If you’re craving a meal, stop for fish and chips from Turner’s Seafood — a local favorite.

Cap off your day by touring a medieval-inspired castle, Hammond Castle, the former home of inventor John Hays Hammond, Jr. You’ll be wowed by both the castle’s interior and the stunning ocean scenery from its grounds.

5. Rockport, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Portland, ME; Portsmouth, NH

Rockport is a sister town to Gloucester, also located on Cape Ann. While there is enough to do in both Gloucester and Rockport for a day, you could plan to see both places in a single trip. Rockport is another historic seaside town that will have you feeling like you stepped into a painting.

Speaking of painting, Motif #1 is a replica of a former fishing shack in Bradley Wharf, and it has been the subject of artists’ paintings and photography for years. If you want a quintessential New England nautical scene, this is your place.

Motif #1 is nestled near Bearskin Neck, a collection of small boutiques and art galleries lined along the harbor. You could spend hours exploring the whimsical variety of items in these shops.

If you’re craving a walk in nature, check out Halibut Point State Park with its many trails that loop along the ocean.

Catch a show at Rockport’s famous Shalin Liu Performance Center, which features an array of musical and dance performances throughout the year. The building is positioned right on the ocean so you can admire the stunning scenery throughout the performance.

And of course, Rockport has its own share of beautiful beaches. Long Beach and Front Beach are two excellent places to sunbathe and swim.

6. York, Maine

Best as a day trip from Ogunquit, ME; Portland, ME; Portsmouth, NH; Boston, MA

The coastal towns continue! York exudes New England charm and boasts a rich history dating back to the early 17th century. Nestled along the southern coast of Maine, York offers a blend of stunning beaches, quaint neighborhoods, and historical landmarks.

A highlight destination in York is Nubble Lighthouse, perched on a rocky island just off the shore. The lighthouse is a short drive from the popular Long Sands and Short Sands beaches.

Grab some ice cream from the parlor at the historic Goldenrod Restaurant and explore the various souvenir shops nearby. Just up the road is the popular York’s Wild Kingdom, part zoo and part amusement park. The park has been providing fun for all ages since 1951!

York is also home to what might be the world’s shortest suspension bridge, Wiggly Bridge. The bridge, which — true to its name — wiggles and jiggles as you walk across, spans York Harbor and leads to peaceful trails in the Steedman Woods.

7. Newport, Rhode Island

Best as a day trip from New Haven, CT; Providence, RI; Boston, MA; Worcester, MA

Newport is one of those places I could visit over and over again and never get tired of it. This historic Rhode Island town is a perfect blend of fascinating architectural sites and stunning natural beauty.

One of the most popular things to do in Newport is walk the scenic Cliff Walk, a 3.5-mile oceanside trail with panoramic views of the Atlantic Ocean almost the entire way.

While in this part of town, you can also tour one of the famous Gilded Age mansions. The most famous mansion is The Breakers, one of the former summer “cottages” of the prominent Vanderbilt family.

🚋 Take a Newport Mansion Trolley Tour

Downtown Newport is filled with interesting shops and restaurants. One of my favorite restaurants is Red Parrot, which has amazing fish and chips. You could also visit the oldest operating restaurant in the U.S., White Horse Tavern.

🍽 Reserve Your Newport Walking Food and History Tour

Stop by Kilwins for ice cream and sit on a bench in Queen Anne Square to look over the beautiful Newport Harbor. Then hop on the Newport Harbor Shuttle at the harbor and take it to Fort Adams State Park. There is a walking path around the entire fort that provides amazing water views the entire way.

8. Block Island, Rhode Island

Best as a day trip from Newport, RI; Mystic, CT; Providence, RI; New London, CT

Block Island is a summer paradise located off the coast of Rhode Island. You can get there by hopping on the one-hour-long Block Island Ferry from Newport or Point Judith, RI, or New London, CT.

Explore the island’s beauty by hiking, biking, or renting a moped.

For breathtaking views of the ocean, visit Southeast Light, a historic lighthouse perched on the Mohegan Bluffs.

The great thing about being on an island is you can find amazing beaches anywhere you turn. Some of the best ones to check out include Crescent Beach, Mansion Beach, and Ballard’s Beach.

There’s also a large natural harbor on the west side of the island called Great Salt Pond, where you can enjoy boating, kayaking, or paddleboarding.

You also can’t miss exploring Block Island’s quaint downtown area, known as Old Harbor. Here you’ll find a charming blend of boutiques, art galleries, and restaurants serving fresh seafood.

For a unique ecological landscape, check out Rodman’s Hollow on the southern part of the island. Part of Block Island National Wildlife Refuge, this large glacial bowl provides awe-inspiring views and is home to a variety of plants and wildlife.

9. Griswold, Connecticut

Best as a day trip from: Mystic, CT; Providence, RI; Newport, RI; Boston, MA

Griswold is a quaint area in southeastern Connecticut with scenic hills and picturesque farmlands. It’s a great day trip option if you want to experience rural New England.

One of my favorite places in this area is Buttonwood Farm, where you can find one of the largest sunflower fields in New England. The sunflowers reach their peak in July and August. Buttonwood also has an ice cream stand with a delicious assortment of flavors — all made fresh on their eco-friendly farm!

For a peaceful walk in nature, visit Pachaug State Forest, the largest state forest in Connecticut, consisting of more than 26,000 acres with 15 trails to explore.

Bonus activity if you visit in the spring instead of summer: Drive from Griswold to nearby Preston to visit the largest “pick your own” tulip farm in New England, Wicked Tulips Flower Farm. The farm is open to flower-pickers in the spring, where you can find over 100 tulip varieties and more than 1.5 million blooms!

10. Watch Hill, Rhode Island

Best as a day trip from Newport, RI; Providence, RI; Boston, MA

Situated on the southwestern tip of Rhode Island, Watch Hill is known for its stunning ocean views and elegant, historic architecture.

Napatree Point Conservation Area is a thin, sandy peninsula stretching out from Watch Hill that’s a preserve for bird nesting and migration. It’s a beautiful area to walk and take in the scenic views on all sides, or sit and relax on one of the pristine beaches.

Watch Hill Lighthouse dates back to 1745 and can be found at the southernmost point of Watch Hill. The lighthouse with its surrounding ocean panoramas is an unforgettable sight to see.

Not far from there, you’ll come to Watch Hill Beach, the perfect place to relax in the sand and sun.

While in Watch Hill, take a ride on the oldest carousel in the U.S., the Watch Hill Merry-Go-Round, known for its “flying horses.”

While this post is focused on day trips, I would be remiss if I didn’t mention the historic Ocean House of Watch Hill, a luxurious seaside resort and the first and only AAA Five Diamond and Forbes Five-Star hotel in Rhode Island. Want to consider extending your visit? 😉

11. Narragansett, Rhode Island

Best as a day trip from Newport, RI; Providence, RI; New Haven, CT; Hartford, CT; Boston, MA

If you’re looking for a pretty Rhode Island beach town without the crowds of places like Newport, try Narragansett, only about a 20-minute drive away. Narragansett is home to beautiful beaches and seaside pathways where you can spend a perfect day in the salty ocean air.

One of my favorite places to visit in Narragansett is Point Judith, a small cape with a historic lighthouse and breathtaking views of the ocean from all sides. If you’re planning a visit to Block Island, there is a ferry that departs from Point Judith, too.

A unique aspect of Narragansett is The Towers, a castle-like structure that crosses Ocean Road and is an iconic venue for public and private events throughout the year. Even if you don’t go inside, the exterior of the building makes for a great photo op.

Near The Towers is a highly-rated seafood restaurant with ocean views called Coast Guard House Restaurant. You’ll also be right by Narragansett Town Beach, a mile-long stretch of sand that is one of the most popular places in Rhode Island for summer beachgoers.

Salty Brine State Beach is another fantastic beach option in Narragansett that’s especially nice for young kids as it’s situated along the seawall and has no waves. Kids will enjoy watching the boats and ferries go by here. Just note that the beach is small and you’ll need to reserve a parking pass ahead of time.

12. Bristol, Maine

Best as a day trip from Portsmouth, NH; Portland, ME; Augusta, ME

With its picturesque harbor and rocky coastline, Bristol captures the essence of Maine’s seaside charm. Come here to enjoy fresh lobster from local fisheries and immerse yourself in the town’s rich maritime heritage through its museums and historic landmarks.

A must-see place in Bristol is Pemaquid Point Lighthouse, where you can climb to the top of the light tower, tour the museum, and climb the rocks along the shore below. The scenery around the lighthouse will take your breath away.

If you’re craving a beach day, Pemaquid Beach Park is known for its gentle waves and smooth, sparkling sand. For a more local, rustic swimming experience, you can also visit The Swimming Hole at Bristol Dam.

La Verna Preserve is a 120-acre nature preserve in Bristol, where you can walk the entire rocky coastline at all tides and enjoy panoramic views of outer Muscongus Bay and its islands.

Not far from Bristol are the Coastal Maine Botanical Gardens, one of Maine’s top attractions. They have a variety of gardens and natural areas, including a butterfly house, bee exhibit, dahlia garden, children’s garden, fairy house village, and much more.

13. Nantucket, Massachusetts

Best as a day trip from various parts of Cape Cod, MA

Nantucket is a timeless, quintessential New England location known for its rich history and maritime culture. This island, located 30 miles off the coast of Cape Cod, offers a picture-perfect combination of pristine beaches, a charming downtown, and iconic grey-shingled houses.

In downtown Nantucket, you’ll find plenty of boutiques and galleries to explore. If you’re a history buff, you might also enjoy the Whaling Museum, which tells the story of Nantucket over four centuries.

Not far from downtown is Brant Point Lighthouse where you can take in beautiful harbor and ocean views.

One of the most remote and breathtakingly beautiful parts of Nantucket is the Costkata-Coatue Wildlife Refuge. At the very end of the seven-mile barrier beach that protrudes from the tip of Nantucket is the historic Great Point Lighthouse. This area of the island is one of the best places to see grey seals!

💡Note that if you plan to drive to Great Point, you will need to purchase a permit from the Trustees. But you can also bike in!

Taking a self-guided bike tour is one of the most popular activities in Nantucket. You can either bring your own bike onto the island or rent from one of the shops downtown.

Of course, since Nantucket is an island, there are beautiful beaches virtually anywhere you go. Some popular beaches include Madaket Beach, Surfside Beach, and Jetties Beach (the most family-friendly option, not far from town).

If you want to see both traditional Nantucket architecture and stunning ocean vistas, try the Sconset Bluff Walk. The path begins near town and winds through residential neighborhoods before opening to a scenic trail along the coast.

14. Litchfield Hills, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Worcester, MA

Litchfield Hills is a picturesque region in northwestern Connecticut filled with rolling hills and charming small towns. Here you can escape the traffic and crowds of more urban parts of New England and take in the scenic beauty of the Connecticut countryside.

Visit the Railroad Museum of New England in Thomaston to learn about the rich railroad heritage of Litchfield Hills. See more than 100 years of carousel history at the unique Carousel Museum in Bristol.

Near the town of Kent, hike the 0.25-mile trail at Kent Falls State Park to admire the series of waterfalls. In the small town of Cornwall, snap a photo of a traditional covered bridge, Cornwall Bridge.

Another prime summer activity in New England is fruit picking! March Farm in Bethlehem lets visitors pick their own cherries, blueberries, and peaches. Mmm.

Best Day Trips in New England in the Fall

It’s no secret that New England is one of the most beautiful parts of the U.S. to see fall foliage and enjoy all the cozy vibes of autumn. Here is my list of favorite New England day trips in the fall!

Scenic Views along Ocean Path in Acadia National Park

15. Acadia National Park, Maine

Best as a day trip from Augusta, ME, or Bangor, ME

Acadia National Park is one of the most beautiful and popular U.S. national parks and one of the best day trip options in New England (though you will likely want to visit for longer!). The park is comprised of more than 47,000 acres of mountains and forests with dramatic ocean vistas that will take your breath away.

One of the best things to do at Acadia is hike or drive to the summit of the largest mountain, Cadillac Mountain (note the Cadillac Mountain Summit Road is only open to vehicles from April to October). If you plan to drive up, you will need to reserve a timed entry slot on Recreation.gov.

Don’t want to drive?
🚌 Reserve a guided bus tour of Acadia National Park from Bar Harbor

Another must-see trail is the scenic Ocean Path Trail with its jaw-dropping ocean panoramas. The trail will lead you down to Sand Beach, one of Maine’s only sandy beaches (hence the name, perhaps?).

Be sure to stop at Jordan’s Pond House Restaurant for their well-known tea and popovers before hiking around Jordan’s Pond and seeing the iconic Bubbles — twin mountain peaks with rounded shapes.

Most of the key attractions at Acadia can be found by driving the scenic Park Loop Road. For a different vantage point, bring your bicycle and ride along the historic carriage roads that wind throughout the park.

Want more ideas of things to do at Acadia National Park? Check out this post!

Golden hour views of Frenchman Bay in Bar Harbor, Maine

16. Bar Harbor, Maine

Best as a day trip from: Bangor, ME; Augusta, ME

Bar Harbor is a picturesque coastal town on Mount Desert Island, right next to Acadia National Park. If you’re planning a trip to the park, it’s worth spending a day here as well.

For fresh Maine blueberry pancakes, start with breakfast at Jordan’s Restaurant. Then walk over to Agamont Park at the end of West Street, where you’ll have scenic views of the Bar Harbor pier and Frenchman Bay.

Try one-of-a-kind flavors at Mount Desert Island Ice Cream, including options like Bay of Figs, Lemon Poppy Berry Jam Swirl, and Salt Wildflower Honey.

You can enjoy your ice cream on a park bench in the Village Green across the street. There’s a community piano in the park’s gazebo that’s open for anyone to play — feel free to stop and plunk out a tune!

Main Street is filled with lots of shops and boutiques to explore, including Maine’s oldest bookstore, Sherman’s Bookstore.

After you’ve finished exploring downtown, you might also enjoy a stroll through Bar Harbor’s neighborhoods with their beautiful homes and gardens.

New England Day Trip: Burlington, Vermont

17. Burlington, Vermont

Best as a day trip from Stowe, VT; Middlebury, VT; Killington, VT

Burlington is a vibrant city on the shores of Lake Champlain, offering a mix of urban life and outdoor adventures. Because it’s home to the University of Vermont, Burlington has a youthful energy that complements its historic charm.

A highlight attraction in Burlington is Waterfront Park, a clean and spacious public park right on Lake Champlain, where you can see the Adirondack Mountains in the distance.

From the park, hop on the Burlington Greenway, an eight-mile scenic bike path that stretches from Queen City Park Road to the Winooski River. If you’re not up for a bike ride, you can also walk part of the trail and stop at the lookout points and beaches along the way.

Church Street Marketplace is another popular part of town. This pedestrian-only street is lined with shops, restaurants, and cafes on either side, where you can easily spend a few hours exploring.

Burlington is where Ben & Jerry’s ice cream was founded, so you definitely should stop for a scoop or two from the Church Street shop.

To experience more of Lake Champlain, book tickets for a Spirit of Ethan Allen cruise. You can enjoy a day tour or reserve a dinner cruise for something a little fancier.

If you’re traveling with kids, it’s also worth going to the ECHO, Leahy Center of Lake Champlain, an interactive science and nature museum on the waterfront.

New England Day Trip: Kancamagus Highway, New Hampshire

18. Kancamagus Highway, New Hampshire

Best as a day trip from Manchester, NH; Montpelier, VT; Bethel, ME

If you google the best places to see fall foliage in New England, the Kancamagus Highway of New Hampshire will likely appear at the top of the list. This 34.5-mile scenic drive begins in the town of Lincoln to the west and ends at North Conway to the east.

Check out these stops along the highway for some of the best leaf-peeping viewpoints:

Lincoln Woods Trail: Walk the suspension bridge over the Pemigewasset River and hike the leisurely out-and-back trail along the river with towering trees overhead.
CL Graham Wangan Overlook: Here you’ll see one of the prettiest views of the Swift River Watershed and White Mountain peaks in the distance.
Sabbaday Falls: A short hike will lead you to this beautiful waterfall, which has a guardrail on one side for you to stand and see the falls up close.
Sugar Hill Overlook: This popular stop features sweeping views of the Swift River Valley and surrounding mountains.
Rocky Gorge: Walk across the small footbridge over the gorge for scenic views of the Swift River.
Albany Covered Bridge: Snap a photo of one of New England’s traditional covered bridges.

19. Northampton, Massachusetts

Best as a day trip from Worcester, MA; Hartford, CT; New Haven, CT; Boston, MA

Northampton is a vibrant and eclectic city nestled in the scenic Pioneer Valley of Massachusetts. The city boasts an array of independent boutiques, art galleries, and live music venues, making it a haven for artists and creatives.

If you love coffee, you could spend a lot of time hopping from one coffee shop to the next in Northampton. There are many options to choose from — one of my favorites is The Roost.

While exploring the shops downtown, take time to admire the street art. There are large murals on the sides of buildings everywhere. It’s one of the features that make Northampton so unique.

Fall is the perfect time for apple picking! Park Hill Orchard and Outlook Farm are both close to Northampton and have pick-your-own areas where you can hunt for your own fruit.

About 15 minutes outside of Northampton is Look Park, filled with a variety of fun and relaxing activities for all ages, including a steamer train, water spray park, mini golf, pedal boats, playgrounds, tennis courts, walking trails, and more.

20. Stockbridge, Massachusetts

Best as a day trip from Worcester, MA; Hartford, CT; New Haven, CT; Albany, NY

Stockbridge is located in the heart of the Berkshire Mountains and offers a mixture of historic architecture and stunning natural landscapes. This town has been an inspiration to writers and artists for generations, including Norman Rockwell, who captured the essence of Stockbridge with his iconic paintings.

Visit the Norman Rockwell Museum to learn more about Rockwell’s life and see some of his original artwork.

Wander along Main Street to explore the antique shops, art galleries, and cozy cafes. Inside the old Stockbridge General Store is Main Street Cafe, which still maintains a lot of the original interior.

Stop by the historic Red Lion Inn (or book a night for the full experience), which has been a landmark of hospitality in the Berkshires for over 250 years. The hotel also owns two local boutiques, Township Four and Shop Around the Corner.

Tour a Gilded Age mansion, Naumkeag, which consists of 44 rooms and eight acres of gardens, including the famous Blue Steps. The property also features a seasonal outdoor Rose Garden Cafe, serving high tea in the gardens on select weekends.

People travel from near and far to visit Tanglewood, the famous summer home of the Boston Symphony Orchestra and a beloved music hall for many prominent musicians. Visit the Tanglewood website for the current line-up of performances.

21. Bennington, Vermont

Best as a day trip from Albany, NY; Stockbridge, MA; Manchester, NH

Surrounded by the stunning natural beauty of the Taconic Mountains, Bennington is a peaceful town filled with tree-lined streets, historic buildings, and a vibrant arts community.

Explore the Bennington Battle Monument, a symbol of Vermont’s role in the American Revolution, and learn more about the city’s history at the Bennington Museum.

See one of New England’s iconic white-steepled churches and Vermont’s oldest Protestant church (dating back to 1805), Old First Congregational Church.

Learn more about the history of Bennington by taking a self-guided Old Bennington Walking Tour (download the brochure from the Bennington website).

Enjoy carefully curated dollhouse exhibits at the Dollhouse and Toy Museum of Vermont. The museum itself is located in a quaint 1850s Victorian home. Bennington is also home to several antique shops, where you can find hidden treasures from days gone by.

If you’re on a hunt to find the most covered bridges in New England, Bennington is home to three of them: the Burt Henry, Paper Mill, and Silk Road bridges.

And for poetry lovers, the Robert Frost Stone House Museum is not far from Bennington, in the town of Shaftsbury.

22. Mystic, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Providence, RI; Newport, RI

Mystic is a 19th-century coastal village that enchants visitors with its scenic waterfront and traditional New England atmosphere. Located on the Mystic River, the town has a timeless charm that points back to its seafaring past.

Step back in time by touring the Mystic Seaport Museum, one of the largest maritime museums in the U.S., and see the nation’s oldest merchant vessel, the Charles W. Morgan whaleship.

⚓️ Take a guided tour of the Mystic Seaport Museum

Mystic’s Main Street has several character-filled boutiques and restaurants to explore. I really enjoyed the seafood at The Mariner.

Not far from downtown Mystic is Olde Mistick Village, a quaint outlet mall with dozens of shops selling handcrafted gifts, jewelry, accessories, and Mystic-made souvenirs.

Another top attraction in Mystic is the Mystic Aquarium, where you can see thousands of species of marine mammals, fish, invertebrates, and reptiles.

23. Marblehead, Massachusetts

Best as a day trip from Boston, MA; Portsmouth, NH; Ogunquit, ME

Marblehead is on the North Shore of Massachusetts and is renowned for its picturesque harbor, rocky shoreline, and beautifully preserved colonial architecture. It’s one of the oldest towns in the United States, with a rich history dating back to 1629.

One of my favorite things to do in Marblehead is browse the cute boutiques, especially along Atlantic Avenue and Washington Street. Sweetwater Trading Company, Chic Streets, and MacRae’s Sustainable Goods are some excellent places to check out.

Shubie’s Marketplace is a great place to stop for lunch. They have a deli counter where you can order delicious, fresh sandwiches, as well as coffee, cannolis, and other treats. If the weather is still nice, they have an outdoor seating area to enjoy, too.

A hidden gem in Marblehead is Castle Rock Park, one of my favorite places in all of New England. It’s located in the middle of a neighborhood, and if you blink, you’ll almost miss the entrance. Once you walk down the short path from the street, you’ll be greeted with the most stunning ocean views. There’s a giant rock formation you can climb to have an even better lookout point.

As weird as it sounds, one of the most picturesque graveyards in New England can also be found in Marblehead, called Old Burial Hill.

Not far from there is the historic Fort Sewall, an old fortification located on Gale’s Head, on the northeastern point of the Marblehead peninsula.

Like many New England towns, it’s also fun to simply walk the residential streets of Marblehead and admire the historic homes, which are kept up well and full of character and charm.

24. Salem, Massachusetts

Best as a day trip from Boston, MA; Portsmouth, NH; Portland, ME

Another North Shore gem is Salem, a town filled with cobblestone streets, colonial architecture, and a host of historic landmarks. It’s best known as the location of the Salem Witch Trials in 1692.

Traveling to Salem from Boston?
🚢 Book a high-speed ferry from Boston’s Long Wharf!

If you are curious about Salem’s dark past, visit the Salem Witch Museum, Salem Witch Trials Memorial, and Old Burying Point Cemetery. Because of Salem’s spooky history, the town is especially popular to visit around Halloween.

Salem is also famous for The House of Seven Gables, a historic home featured in Nathaniel Hawthorne’s 1861 novel of the same name. You can purchase tickets to tour the house and grounds.

Another key attraction in Salem is the Peabody Essex Museum, featuring over 1.8 million pieces of art, architecture, and cultural artifacts. What started as a collection of objects by Salem sea captains in 1799 has turned into one of the most famous museums in Massachusetts.

If you’re craving something sweet, stop by Harbor Sweets for some locally-made chocolate and other sugary goodness. Their sailboat-shaped Sweet Sloops, made of almond buttercrunch, white and dark chocolate, and pecans, are one of their most popular items. (I’ve tried them and can attest that they’re delicious!)

25. East Haddam, Connecticut

Best as a day trip from Hartford, CT; New Haven, CT; Providence, RI

Nestled along the Connecticut River, East Haddam offers a picturesque setting with rolling hills, peaceful rivers, and dense forests.

One of the top attractions in East Haddam (and all of Connecticut actually) is the quirky Gillette Castle, the former home of actor William Gillette. Pay to tour inside the fascinating residence or simply walk the grounds, which provide scenic views of the Connecticut River.

Devil’s Hopyard State Park has hundreds of acres of beautiful hiking trails. One of the most popular stops in the park is Chapman Falls, whose staircase-like shape represents what some people say to be the “devil’s footpath.”

Just outside of Devil’s Hopyard, stop by Boho Farm, a small family-owned farm near town with a gift shop selling handmade and locally sourced items.

Walk around East Haddam’s quaint Main Street to explore its boutiques and grab some ice cream. See a show at the iconic Goodspeed Opera House in town, which has been hosting performances since the 19th century.

Best Day Trips in New England in the Winter

Winter is a beautiful time to visit New England. Escape the crowds of summer and fall while still taking in the natural beauty and historic sites of the region. And of course, if you’re into winter sports like skiing or ice skating, then this is the prime time to go!

Here are my top picks for New England day trips in the winter:

26. Stowe, Vermont

Best as a day trip from Burlington, VT; Killington, VT; North Conway, NH

Located in northern Vermont, Stowe is known as the birthplace of alpine skiing in the state. Its first lift-operated ski trail started in 1937 on Mount Mansfield (the tallest point in Vermont at 4,939 feet).

The Stowe Mountain Resort is the place to be if you want to ski in Stowe. With 116 trails and 12 lifts, it has been an internationally acclaimed ski resort since the 1940s. Not far from Stowe is another popular skiing location, Smugglers’ Notch Resort.

If you’d prefer ice skating over skiing, there is a complimentary ice rink at the Spruce Peak Village Center, part of Stowe Mountain Resort. You can bring your own skates or rent them on-site.

Downtown Stowe is filled with quaint shops, galleries, and restaurants to explore — a great way to escape the winter cold. Be sure to snap a photo of the iconic white-steepled Stowe Community Church.

Another popular activity is the Stowe Recreation Path, which stretches from Stowe Village to Top Notch Resort on Mountain Road. In the winter, this 5.3-mile trail is open to walkers, runners, bikers, cross-country skiers, and snowshoers. There’s also a free shuttle that provides transportation along Mountain Road if you want to make it a one-way trip!

27. North Conway, New Hampshire

Best as a day trip from Manchester, NH; Portland, ME; Augusta, ME

North Conway is a scenic town in the heart of the White Mountains, in Mt. Washington Valley, and the perfect place to spend a snowy winter day.

In the town of North Conway itself, spend time browsing more than 100 shops, galleries, and factory outlets in North Conway Village.

If you’re interested in skiing, North Conway is within easy driving distance from three popular resorts: Cranmore Mountain Resort (5 minutes), Attitash Mountain Resort (15 minutes), and King Pine Ski Area (25 minutes).

While people flock to the Kancamagus Highway in the fall as one of the prime areas to see colorful foliage, this scenic road is equally beautiful in the winter with the snow-covered mountain peaks and fir trees. Just check the weather before you go as the highway sometimes closes when it snows.

North Conway isn’t far from Mount Washington, the tallest peak in the northeastern United States, towering at 6,288 feet.

The Mount Washington Auto Road is closed to private vehicles in the winter, but you can book a ride on a SnowCoach that takes you up two-thirds of the way, where you’ll have amazing views of the Presidential Range.

Hop on a traditional steam locomotive at the Conway Scenic Railroad. While train times are more limited in the winter, the company still offers picturesque trips through the snowy White Mountains. Check the website for available tours and to book tickets in advance.

If you don’t mind driving an hour to the other end of the Kancamagus Highway, experience the Ice Castles of New Hampshire in North Woodstock. This icy paradise includes ice slides, caves, and crawl tunnels, as well as an illuminated walking path, a snow tubing run, a Winter Fairy Forest, and more.

28. Killington, Vermont

Best as a day trip from Burlington, VT; Stowe, VT; Manchester, NH

On the Green Mountains side of New England lies the town of Killington, one of the most beloved skiing areas in the eastern United States.

Killington Resort is referred to as “The Beast,” with 1,509 skiable acres, 155 trails, and 21 lifts. Its tallest trail has an impressive 3,050-foot vertical drop.

Pico Mountain Ski Resort and Okemo Mountain Resorts are two other popular resorts not far from Killington.

If you fancy snowshoeing over skiing, try one of the trails in Gifford Woods State Park. This park is a common pass-through area for hikers on the Appalachian Trail from Georgia to Maine.

For an easy winter hike, the two-mile out-and-back Deer Leap Overlook Trail leads to a rock outcrop with beautiful views of the Coolidge Mountain Range and Sherburne Pass.

After a long day in the snow, warm up with a hearty dinner in downtown Killington. A couple of highly-rated restaurants include Casey’s Caboose and The Garlic.

New England Day Trip: Washington, Connecticut

29. Washington, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Albany, NY

Washington is a picturesque town in the Litchfield Hills of western Connecticut. Known for its charming New England ambiance, it offers a peaceful retreat away from the hustle and bustle of city life.

See the beautiful, white-steepled First Congregational Church before strolling through Washington’s quiet neighborhoods with their historic and well-landscaped homes.

Stop for lunch at Po Cafe, located in the old post office building. They have a delicious selection of food and drinks with both indoor seating and heated outdoor seating. (Note they are closed on Sunday and Monday and are only open until 2 p.m. on the other days.)

For a luxurious winter day trip experience, book a special spa treatment at the renowned Mayflower Inn & Spa. (If you’re a Gilmore Girls fan, this place inspired the creation of the Independence Inn on the show.)

Washington is also home to three scenic nature preserves, the Hidden Valley, Macricostas, and Steep Rock preserves. Each of these preserves allows cross-country skiers and snowshoers on their hiking trails during the winter months. Enjoy snow-covered landscapes as you glide along the various loop trails.

30. Concord, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Hartford, CT; Manchester, NH

Concord is a picturesque town just a short drive from Boston, with an interesting blend of colonial architecture, historic sites, and literary landscapes.

Concord looks like a postcard in the winter, especially during the Christmas season when its quaint Main Street is beautifully decorated with wreaths and lights.

One of my favorite shops in downtown Concord is Nesting, an eclectic boutique with unique gifts and home goods. You can find lots of Christmas ornaments and other winter decor there this time of year.

Another highlight attraction near Concord that’s open year-round is Minute Man National Historic Park, which preserves the sites involved in the first armed conflict of the American Revolution on April 19, 1775. A key place to visit in the park is Old North Bridge, where the famous “shot heard round the world” was fired.

Walden Pond State Reservation is the place that inspired Henry Wadsworth Longfellow’s novel Walden. Take a peaceful winter hike around the pond and you’ll come across the former site of his log cabin where he wrote the book.

For another historic, literary experience, take a tour of the Louisa May Alcott Orchard House, the home where the famous author wrote and set her novel Little Women in 1868.

31. Bethel, Maine

Best as a day trip from Portland, ME; Augusta, ME; North Conway, NH

Bethel is a popular ski town in Maine and is referred to as “Maine’s most beautiful mountain village.”

Sunday River Resort is one of Maine’s largest ski resorts with 19 lifts and 139 different trails and glades. It’s also home to the fastest eight-person chairlift in North America.

Not far from Sunday River Resort is the Sunday River Covered Bridge, built in 1872 and part of the U.S. National Register of Historic Places.

Mt. Abram Ski Area is a smaller ski resort near Bethel that is a popular choice for families and first-time skiers, or those looking for a quieter, more local skiing experience.

Another “gem” in Bethel is the Maine Mineral and Gem Museum, where you can see meteorites from Mars, the moon, and the Asteroid Belt. There’s also a Rock Garden showcasing 26 geological specimens from around the state.

If you’re up for a good winter hike, try the Old Speck Trail in Grafton Notch State Park, a 7.6-mile round-trip trail that ascends Maine’s third-highest mountain at 4,180 feet. There are also places in the park to cross-country ski or snowshoe.

Best Day Trips in New England in the Spring

New England gets a lot of press in the fall with its beautiful foliage colors, but I absolutely love it here in the spring. New England often has very harsh winters, so there’s nothing quite like seeing those first blooms after the snow has melted away. The weather starts to warm up, but you don’t have to worry about the crowds and traffic of summer.

Here are my top recommendations for New England day trips in the spring:

32. Boston, Massachusetts

Best as a day trip from Worcester, MA; Providence, RI; Hartford, CT; Manchester, NH; Ogunquit, ME

Boston makes for a great day trip in New England at any time of the year, but I especially love the city in the spring. After a long, harsh winter, it’s so pretty to see all the trees come into bloom, and the streets come alive with people once again.

To understand Boston’s important role in the American Revolution, take a guided or self-guided tour of the Freedom Trail, a 2.5-mile path that leads you to 16 different historic sites throughout the city. You can also experience a reenactment of the Boston Tea Party at the Boston Tea Party Ships & Museum.

🇺🇸 Book a guided Freedom Trail tour

Learn more about Boston’s history on a one-of-a-kind Duck Boat Tour, an amphibious vehicle that takes you past sights on both land and water.

🦆 Book your Duck Boat Tour (They sell out fast!)

Taste authentic Italian food in North End, also known as Boston’s Little Italy. Mike’s Pastry and Modern Pastry are rivals for the best cannoli. (Most locals seem to point to Modern Pastry, though I think both of them are good — but hey, I’m no cannoli connoisseur.)

Experience Boston’s Chinatown, a center of Asian-American life in New England. There are many amazing Asian restaurants to choose from, and I love to go here for bubble tea!

Walk over to Copley Square and tour the Boston Public Library, especially the historic section of the library that includes the stunning Bates Hall.

Spend some time browsing the shops along Newbury Street with its iconic brownstone buildings before heading to the Charles River Esplanade for scenic water and city views.

A visit to Boston wouldn’t be complete without walking through the Public Garden and Boston Common, two of America’s oldest and best public parks.

End your day with a walk down Charles Street in the charming Beacon Hill neighborhood (one of my favorite places in Boston!). If you have time, sneak up to Acorn Street to see one of the last original cobblestone streets in Boston. It’s one of the most photographed streets in America.

33. Martha’s Vineyard, Massachusetts

Best as a day trip from Provincetown, MA; Hyannis, MA; Providence, RI; Boston, MA

Martha’s Vineyard is a prime island getaway in New England, just off the coast of Cape Cod, Massachusetts. The high season for the island is in the summer, so I recommend visiting in May if you want to beat the crowds. (But if you want to see the stunning hydrangeas, those typically don’t start blooming until July.)

The only way to get to Martha’s Vineyard is by ferry or plane. There are several places to catch the ferry, including the Falmouth and Hyannis harbors on Cape Cod. There are also tour options from Boston!

🚢 Book a Martha’s Vineyard Day Trip from Boston

Once you get to the island, spend some time exploring the various shops and boutiques downtown, including the beloved Vineyard Vines store that was founded on the island.

Visit the Oak Bluffs area of the island to see the iconic gingerbread cottages. In this neighborhood, you will also find the Flying Horses Carousel, the oldest operating platform carousel in America. The carousel was first located in New York City but was moved to Martha’s Vineyard in the 1880s.

For stunning cliff and ocean views, stop by the Aquinnah Cliffs Overlook on the western side of the island. (This is an awesome place to watch the sunset, too!)

One of the best beaches on Martha’s Vineyard is South Beach, located on the southeast side of the island. But you really can’t go wrong — you’ll find stunning beaches all over Martha’s Vineyard.

34. Provincetown, Massachusetts

Best as a day trip from Boston, MA; Hyannis, MA; Plymouth, MA

On the tip of Cape Cod is the charming town of Provincetown. It’s the oldest continuous art colony in the United States, with numerous galleries, studios, and theaters showcasing the work of local artists. And with Provincetown stretching 60 miles into the ocean, it’s also filled with natural beauty and seaside fun.

Note that you can drive to Provincetown if you want to see the entire Cape, or take a ferry directly there from Boston’s Long Wharf.

Commercial Street is the center of activity in Provincetown, where you’ll find numerous shops and restaurants to explore.

Provincetown is also a prime location to catch a whale-watching tour. Boats depart from the Provincetown Harbor and last for 3-4 hours, giving you ample opportunity to see a variety of whales and dolphins in their natural habitat.

Check out the 252-foot-tall Pilgrim Monument, which is the actual place where the pilgrims first landed in the New World before sailing on to Plymouth.

The monument is part of the Provincetown Museum, where you can learn more about the Mayflower pilgrims’ arrival and the rich maritime and theater history of Provincetown.

Two of the best beaches in Provincetown include Race Point Beach and Herring Cove Beach. You may not want to swim yet in the spring, but it’s still worth walking along the shore or relaxing on the sand.

The Race Point Lighthouse is also worth seeing when you’re in Provincetown, but note that contrary to the name, the lighthouse is about a two-mile hike (or 11-minute drive) from Race Point Beach.

Province Lands Bike Trail, one of three bike trails at Cape Cod National Seashore, is a 5.45-mile trail winding through pine forests, sandy dunes, and cranberry bogs. The trail includes easy exit points to Race Point Beach and Herring Cove Beach.

35. New Haven, Connecticut

Best as a day trip from Hartford, CT; Mystic, CT; Providence, RI; New York, NY

New Haven is on the southwestern side of Connecticut, about an hour and a half from New York City. It’s a dynamic and diverse city with a vibrant academic atmosphere, rich history, and plenty of natural beauty to explore.

New Haven is most famous as the home of Yale University, one of America’s oldest and most prestigious colleges, founded in 1701. Book a walking tour to learn more about the university’s history and take in the stunning architecture.

Not far from Yale’s campus is the historic New Haven Green that has been around since 1638. Walk through this nine-acre green space, enjoy the canopy of elm trees above you, and stop to see three of New Haven’s historic churches: Trinity Church, United Church, and Center Church.

From the Green, walk a short distance to Louis’ Lunch, one of the tiniest restaurants you’ll ever see. This little hamburger joint has been around since 1900, and they still serve their burgers on toast.

If you’re craving time in nature, visit Lighthouse Point Park for scenic views of New Haven and Long Island Sound.

Another popular option is East Rock State Park, a unique trap rock formation in the middle of the city. Hike to the top of the “rock” for a birds-eye view of New Haven and Long Island Sound beyond.

In the neighboring town of Hamden, hike the trail around the peaceful Lake Wintergreen.

Bonus: About 20 minutes outside of New Haven, in Milford, is Silver Sands State Park, one of my favorite places in Connecticut.

This unique seaside park includes a sandy beach, boardwalk, and — the most unique feature — a “tombolo” (sandbar) that you can walk across to Charles Island only during low tide. (Be sure to come back before the tide rises or you’ll be stuck on the island with the nesting birds!)

36. Beverly, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Portsmouth, NH; Ogunquit, ME

Beverly is a hidden gem on the Massachusetts North Shore. Most people mention towns like Gloucester and Rockport when they talk about escaping the city for a day by the shore, but there are several attractions that make Beverly worth a visit, too.

Start your day in Beverly with a delicious cup of coffee and fresh scone from the tiniest little cafe you may ever see: Beantrust Coffeebar. There isn’t much space inside to sit and relax, but it’s worth grabbing your items to-go and strolling through the pretty neighborhoods nearby.

Lynch Park is known as the Crown Jewel of Beverly with its beautiful rose garden, beaches, amphitheater, playground, and splash pad. It’s the perfect place to spend an afternoon near the water. (Note that parking is $15 on weekdays and $25 on weekends during high season from the end of May through Labor Day.)

Dane Street Beach is one of the most popular beaches in Beverly, and one of the few beaches on the North Shore where you can find free street parking. You may not want to swim in the water in the spring, but it’s still a beautiful beach for a walk or to sit and watch the waves roll in.

See a show at the North Shore Music Theatre, the largest operating theatre in New England, attracting more than 250,000 people each year. It’s also one of the few remaining “theatre-in-the-round” stages left in the U.S.

Enjoy the lovely gardens and walking trails at Long Hill, the former summer home of the Sedgwick family from 1916 to 1979.

37. Hartford, Connecticut

Best as a day trip from New Haven, CT; Boston, MA; Worcester, MA; Providence, RI

Located in central Connecticut, the state’s capital city of Hartford offers an interesting mix of historic sights, public parks, and high-quality museums to explore.

The Connecticut State Capitol is one of the most beautiful capitol buildings I’ve ever seen, with its gold dome and Victorian Gothic architecture. Surrounding the capitol is the scenic Bushnell Park, featuring a historic carousel and several monuments.

Another beautiful park to check out is the Elizabeth Park Conservancy. Its focal point is the Helen S. Kaman Rose Garden with its many arches of roses that come into full bloom by mid-June.

Tour the 25-room mansion where the iconic author Samuel Langhorne Clemens (Mark Twain) and his family lived from 1874 to 1891. The Mark Twain House & Museum has been designated a National Historic Landmark.

If you’re interested in art history, visit the Wadsworth Atheneum Museum of Art, which is home to nearly 50,000 works of art spanning 5,000 years.

The Connecticut Science Center and The Children’s Museum are two other fun places to visit in Hartford if you have kids. Both museums are full of interactive exhibits where kids can try their hand at STEM activities and see scientific wonders.

Best New England Day Trips for Families

New England is a wonderful place to visit with the whole family! So many locations have attractions geared toward kids, and there are plenty of activities that can entertain all ages.

These are some of my top recommendations for family day trips in New England:

Hartford, Connecticut: Kid-focused museums and parks
Mystic, Connecticut: Fun maritime activities, including a historic ship and large aquarium
Acadia National Park, Maine: Endless hiking trails and areas to explore
Ogunquit, Maine: Shoreside fun, with beaches, trails, kayaking, and more
York, Maine: Home to one of New England’s largest zoos and awesome beaches
Boston, Massachusetts: Playgrounds, parks, and museums galore!
Gloucester, Massachusetts: Family-friendly beaches and a hidden castle
North Conway, New Hampshire: Snowy paradise with ice castles, ski resorts, and more
Burlington, Vermont: Lakeside parks, hiking trails, and a one-of-a-kind science museum

Best New England Day Trips for Couples

If you’re planning a romantic trip for two, here are my favorite options:

Litchfield Hills, Connecticut: Small towns and scenic landscapes to explore
Bar Harbor, Maine: Relaxing restaurant and cafe scene at the doorstep of Acadia National Park
Portland, Maine: Foodie paradise along with plenty of outdoor activities
Martha’s Vineyard, Massachusetts: Quaint island getaway with lots of history and charm
Nantucket, Massachusetts: Similar to Martha’s Vineyard, but even more remote
Portsmouth, New Hampshire: Walkable downtown and close proximity to beaches
Stowe, Vermont: Cozy mountain escape

Best Places to Stay in New England

If you’re taking multiple day trips in New England and need a “base camp” where you can crash for the night, here are some excellent options throughout the region: