7-Day New England Road Trip Itinerary: All 6 States from Boston (2026)

Planning a 7-day New England road trip itinerary from Boston?

Ah, New England. I have long been smitten with this historic region of the country, which includes Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

Having lived in New England for more than five years and traveled the region for 20+ years, I know the BEST places to see if you’re visiting for a short time.

Once you arrive in New England, you will likely wish you could stay much longer than 7 days. However, there are several highlight spots you can reach in one week to get a good taste of the region. That’s the list I have curated for you in this 7-day New England road trip itinerary!

Have more or less time to spare? I’ve also included 10-day and 5-day itinerary options to help you maximize your trip.

⏰ SHORT ON TIME?

🛌 DESTINATIONS + WHERE TO STAY
DAY 1: Boston, Massachusetts: Hyatt Regency Boston Harbor
DAY 2: Newport, Rhode Island: Hotel Viking
DAY 3: Mystic to Washington, Connecticut: Mayflower Inn & Spa
DAY 4: Stockbridge, Massachusetts to Killington, Vermont: Mountain Meadows Lodge
DAY 5: Stowe, Vermont: Trapp Family Lodge
DAY 6: White Mountains, New Hampshire: New England Inn & Lodge
DAY 7: Portland, Maine and Portsmouth, New Hampshire: Hampton Inn & Suites

🚗 NEED A CAR?
Book through Discover Cars for some of the best rates

7-Day New England Road Trip Itinerary

This road trip is a loop that begins and ends in Boston, Massachusetts, the largest city in New England. If you plan to fly to New England and rent a car there, you can usually find the best flight deals into Boston.

From Boston, you’ll travel south to Rhode Island and Connecticut, north through western Massachusetts and into Vermont, northeast to New Hampshire and Maine, and then back down to Boston.

🚗 WHAT TO EXPECT FROM THIS ROAD TRIP ITINERARY 🚗

I crafted this itinerary as a true “road trip,” meaning lots of time on the road and hopping from place to place. I personally love traveling this way because of the variety of things you can see in a short period of time.

However, I know this type of pace is not for everyone. If you’d rather stay in certain places longer, you could easily cut other destinations out. Make this trip feel right for you!

Day 1: Boston, Massachusetts

Driving time: None! This itinerary assumes you arrive in Boston early and have the full day to explore, then stay overnight here.

Kick off your 7-day New England itinerary with a tour of Boston. Explore North End, Boston’s Little Italy, to taste authentic Italian food, and then begin walking along the historic Freedom Trail by Old North Church.

Stop by Faneuil Hall Marketplace, known as the Cradle of Liberty because patriots would meet here in the days leading up to the Revolutionary War. Not far from Faneuil Hall you can also see Boston’s Old State House, Old South Meeting House, and the Benjamin Franklin statue.

Have lunch in Boston’s Chinatown, a center of Asian-American life in New England. Then walk over to Copley Square and explore the beautiful Boston Public Library (don’t miss Bates Hall!).

Browse the shops along Newbury Street before walking the Charles River Esplanade for scenic city views. End your day in Boston by exploring the picturesque cobblestone streets of Beacon Hill and walking through Boston Common and the Public Garden.

🇺🇸 For a fun way to learn about the history of Boston, check out this popular walking tour with an emphasis on storytelling.

➡️ See my 24 hours in Boston post for a more detailed list of things to do in Boston in a day, along with a sample route map.

Where to Stay in Boston

📍Hyatt Regency Boston Harbor: Mid-range hotel with great views of the Boston Harbor.

📍Omni Parker House: One of Boston’s most iconic and historic hotels, in operation since 1855.

Day 2: Newport, Rhode Island

Driving time: 71 miles (roughly 1.5 drive from Boston to Newport)

Only 1.5 hours south of Boston is the beloved coastal town of Newport, Rhode Island. It’s my husband and my favorite place in Rhode Island and one we never get tired of visiting.

The best thing to do in Newport is walk the scenic Cliff Walk, a 3.5-mile scenic trail with stunning views of the Atlantic Ocean almost the entire way. While you’re near the Cliff Walk, it’s also worth stopping by one of the iconic Newport mansions for a tour. The most famous of the mansions is The Breakers.

Book this five-star-rated Newport trolley tour for an easy way to tour the Breakers and see other key sites in Newport. ⭐️⭐️⭐️⭐️⭐️

Downtown Newport, especially Thames Street, is bustling with shops and restaurants within traditional New England architecture. The Red Parrot restaurant has delicious fish and chips, but if you want to visit the oldest operating restaurant in the U.S., go to White Horse Tavern.

🦀 Want to experience more of Newport’s food scene? Check out this highly-rated food and history walking tour.

After that, it’s worth stopping by Kilwins for ice cream and enjoying it on a bench in Queen Anne Square while looking out at Newport Harbor.

If you have time to spare, hop on the Newport Harbor Shuttle to Fort Adams State Park and take a walk around the old fort for beautiful water views.

Where to Stay in Newport

📍Jailhouse Inn: Stay in an actual former jail that dates back to 1772 and is on the National Register of Historic Places. This place is now a quirky bed and breakfast that’s retained some of its original jail features, like steel bars on the windows.

📍Hotel Viking: On the list of Historic Hotels of America, this hotel is also full of character and charm and within convenient walking distance of Newport’s downtown.

Day 3: Mystic to Washington, Connecticut

Driving time: 145 miles (roughly 1 hr from Newport to Mystic and 1 hr, 45 minutes from Mystic to Washington)

On day 3 of this 7-day New England road trip, you will head one hour west to the moody port town of Mystic—one of Connecticut’s most beautiful places.

Here you will find one of the largest maritime museums in the United States, Mystic Seaport, as well as the oldest merchant vessel in the U.S., the Charles W. Morgan whaleship.

The main street of Mystic has several cute boutique shops and restaurants. If you’re craving seafood, you might enjoy The Mariner for a tasty lunch. Their menu ranges from oysters and clams to fish and lobster.

If you’re a book lover, it’s worth visiting the Book Barn in Niantic for an hour or two. It’s one of the largest used booksellers in New England with more than 500,000 books, and it’s only about a 25-minute drive west of Mystic.

From there, you will drive about 1.5 hours northwest to the charming town of Washington, Connecticut.

Park near the old post office, which is now the popular Po Cafe serving delicious food and drinks. (Note they are only open until 2 p.m. and are closed on Sunday and Monday, so I suggest coming here for breakfast on Day 4.)

Not far from the cafe, you can walk past the picturesque First Congregational Church, a large white-steepled church typical of New England, and then stroll through the quiet neighborhoods with their quaint, well-landscaped homes.

Where to Stay in/Near Washington

📍Mayflower Inn & Spa: This is the place to stay if you’re looking for a splurgy treat. And if you’re a Gilmore Girls fan, this hotel will be especially meaningful, as it’s said to have inspired the Independence Inn on the show.

📍Litchfield Inn (in Litchfield, about 20 min. from Washington): Stay in a classic colonial estate with 32 guest rooms and 10 acres of beautiful grounds to explore.

Day 4: Stockbridge, Massachusetts to Killington, Vermont

Driving time: 176 miles (roughly 1 hr, 20 min from Washington to Stockbridge and 2.5 hours from Stockbridge to Killington)

Start your day with breakfast at the Po Cafe in Washington before driving about an hour and 20 minutes north to the historic town of Stockbridge, Massachusetts, located in the scenic Berkshires highlands.

Inside the old Stockbridge General Store building is Main Street Cafe, which still maintains a lot of the original interior. The old general store was made famous in one of Norman Rockwell’s paintings.

Speaking of Norman Rockwell, the Norman Rockwell Museum is also located in Stockbridge, if you want to see some of the original artwork from the iconic American painter.

After spending some time in Stockbridge, you’ll continue driving about 2.5 hours north into the lush Green Mountains of Vermont.

If you’re up for a hike after all that driving, you could do the moderate 2-mile out-and-back Deer Leap Overlook Trail near Killington, which takes just over an hour to complete.

Finish the day with a hearty dinner at Casey’s Caboose or The Garlic, both located in Killington.

Where to Stay in Killington

📍Mountain Meadows Lodge: Cozy rooms and delicious breakfast, with gorgeous mountain views.

📍The Snowed Inn: Close to Killington ski resort, this hotel has a year-round outdoor hot tub.

Day 5: Stowe, Vermont

Driving time: 75 miles (roughly 1.5 drive from Killington to Stowe)

On day 5 of this 7-day New England road trip, you will visit the magical town of Stowe, Vermont.

About an hour and a half north of Killington, Stowe is known as the birthplace of alpine skiing in Vermont. Its first lift-operated ski run began in 1937 on Mount Mansfield (the tallest point in Vermont at 4,939 feet).

However, Stowe is great to visit any time of the year. In the fall, tourists flock here for some of the best fall foliage vistas in New England. Spring is the perfect time to go on a maple syrup tour to learn how Vermont’s famous sugary goodness is made.

In the fall, spring or summer, enjoy one of Stowe’s many hiking and biking trails or kayak along the Winooski or Lamoille Rivers.

Best hiking trails in Stowe

• Stowe Pinnacle via Pinnacle Meadow Trail (Moderate): This 3.2-mile out-and-back trail takes about two hours to complete and connects with the popular—but more challenging—Stowe Pinnacle Trail that leads up to Stowe Pinnacle.
  
• Bingham Falls Trail (Easy): This 0.5-mile out-and-back trail only takes about 20 minutes to complete and provides lovely views of Bingham Falls at the end. People have commented that the rocks can get slippery near the bottom, so be careful!
  
• Stowe Recreation Path (Easy): This paved 5.5-mile, out-and-back greenway is great for bikes and strollers. There are numerous shops and restaurants along the path where you can stop to browse or grab a bite to eat.

Other things to do in Stowe

• Visit Moss Glen Falls located along the scenic VT 100 highway.
• Tour Smugglers Notch State Park and drive the VT 108 highway.

Where to Stay in Stowe

📍Green Mountain Inn: Rooms decorated in handcrafted Vermont furnishings, located in the center of historic Stowe.

📍Trapp Family Lodge: Austrian-inspired architecture and furnishings with gorgeous mountain views.

Day 6: White Mountains, New Hampshire

Driving time: 132 miles (roughly 2 hours from Stowe to Lincoln, NH, then a scenic drive along the 34.5-mile Kancamagus Highway)

Now that you’ve experienced the Green Mountains of Vermont, drive a couple hours east to the White Mountains of New Hampshire.

Start in the small town of Lincoln, where you will find the beginning of the famous Kancamagus Highway, a scenic 34.5-mile drive through White Mountain National Forest. There are numerous stops along the highway for stunning outlooks and hiking trails:

• Lincoln Woods Trail: This is one of the first stops along the Kancamagus Highway. Walk the suspension bridge over the rocky Pemigewasset River and you’ll end up on a leisurely out-and-back trail along the river with towering trees overhead.
  
• CL Graham Wangan Overlook: From this point, you will have 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. There is a picnic area nearby, making for a picturesque spot to enjoy lunch.
  
• Sugar Hill Overlook: This is one of the most popular viewpoints along the Kancamagus Highway, where you can see the Swift River Valley and surrounding mountains.
  
• Rocky Gorge: Take the small footbridge across the gorge for scenic views of the Swift River.
  
• Albany Covered Bridge: See one of New England’s traditional covered bridges right along the Kancamagus Highway.

The Kancamagus Highway ends near North Conway, where you can enjoy a laid-back, all-American meal at the highly-rated Muddy Moose Restaurant & Pub or Delaney’s Hole in the Wall.

Where to Stay in North Conway

📍New England Inn & Lodge: Comfortable and cozy rooms in a wood cabin-style hotel.

📍White Mountain Hotel & Resort: Features a heated pool and hot tub overlooking the mountains.

Day 7: Portland, Maine to Portsmouth, New Hampshire and back to Boston

Driving time: 168 miles (roughly 1.5 hours from North Conway to Portland, 1 hour from Portland to Portsmouth, and 1 hour from Portsmouth to Boston)

On the last day of this 7-day New England road trip, head southeast to the iconic coastal town of Portland, Maine. Here you will see a blend of traditional New England architecture and history, along with contemporary, artsy vibes.

Visit Bug Light Park to see the beloved Bug Light, standing at only 26 feet tall, and walk along the scenic Eastern Promenade for stunning views of Casco Bay.

Take a ride on the historic Maine Narrow Gauge Railroad, and snag some fresh seafood from the Portland Farmer’s Market (open Wednesdays and Saturdays) or Harbor Fish Market.

The #1 thing to do in Portland is visit America’s most photographed lighthouse, Portland Head Light, located on Cape Elizabeth. Not only is the lighthouse itself beautiful, but the surrounding landscape will take your breath away.

The very last stop on this 7-day New England road trip is Portsmouth, New Hampshire, another picture-perfect town about an hour from Cape Elizabeth.

Park downtown and browse the shops and boutiques along Congress Street. For dinner, I highly recommend The Flatbread Company, which makes delicious wood-fired pizza with locally sourced ingredients.

Where to Stay in or near Portsmouth

📍Hampton Inn & Suites: Centrally located in Portsmouth with breakfast included, this hotel is a short walking distance from restaurants and other town attractions.

📍Wentworth by the Sea: Located in New Castle, just outside of Portsmouth, this dreamy hotel offers cozy rooms with stunning harbor views. I’ve stayed here a couple of times and absolutely loved it.

Portsmouth is about an hour from Boston, where you can return to end your epic New England road trip!

Note: Technically, if you stay overnight in Portsmouth, you’d be driving back to Boston on Day 8. If you’re truly locked in to seven days including travel time, you could skip Portsmouth on Day 7 and drive straight back to Boston from Portland OR drive back to Boston late on Day 7 after splitting the day between Portland and Portsmouth.

New England 7-Day Road Trip Map

Such a beautiful circle, covering a lot of ground!

Know Before you Go: Road Trip Tips

Driving in New England

Driving can be unpredictable in New England, especially in densely populated or touristy areas like Boston, Newport, Acadia and Cape Cod. 

While it might be hard to completely avoid traffic, there’s less congestion during workdays (outside rush hour), so it might be good to plan your stops in more touristy destinations on weekdays instead of weekends.

The driving itself is pretty straightforward. Many rural and scenic roads are narrow and winding (and can be icy in winter months), so use some caution there.

🌟 Fun fact: In New England, roundabouts are called “rotaries” (which I find most endearing). You’ll often see these being used instead of intersections with traffic lights. The same rule as usual applies: Yield to traffic within the circle.

Boston deserves its own special mention here:
When you’re in Boston, I’d recommend keeping your car parked at your hotel or elsewhere and using public transportation or walking to get around. 

Not only can the traffic be crazy, but the roads are also not in a typical grid-like pattern (thanks to being one of the country’s oldest cities!) and there are a LOT of underground tunnels that veer in many different directions. It’s easy to get a bit turned around if you’re not paying attention. 

“The T,” Boston’s subway, is pretty reliable and easy to navigate, and it’s my preferred way to get around the city (after walking).

Cell service

Like most places, cell service in New England is best in cities and towns and spottier in more rural areas. At Acadia National Park and in the White Mountains, in particular, I remember not having much cell service at all. 

If you think you’ll want a map to navigate around, I’d recommend downloading it on your phone ahead of time or keeping a printed version on hand.

What to pack

I’m a bit of a minimalist when I travel, trying to never fly with more than a carry-on. So that means sticking to the essentials. 

Here are the key items I would pack for a 7-day road trip in New England.

CLOTHING AND ACCESSORIES

• Waterproof jacket for rainy days, or a thicker coat if you’re going in winter
• Hat, scarf and gloves for colder months; swimsuit, sunhat and sandals for warmer months
• Light layers like sweaters or sweatshirts for cooler evenings (even in summer!)
• Sturdy sneakers or hiking shoes if you plan to hike some trails
• Comfortable walking shoes for exploring cities and towns, many which have cobblestone walkways
• Bug spray and sunscreen, especially in summer

FOR THE CAR

• Phone mount and charger
• Offline maps downloaded for your route, in case cell phone coverage drops in places like rural Vermont, New Hampshire or Maine
  • Consider also having a printed map on hand just in case
• Reusable water bottle and snacks
• Basic first aid kit and any medications
  • Dramamine may also be handy if you plan to do any boat cruises and are prone to motion sickness
• And of course, don’t forget your driver’s license, insurance and any rental car confirmation. 😉

Parking

Parking can vary across New England, but here are a few key points to keep in mind:

• In Boston, expect pricey parking garages or metered street parking (mostly parallel).
• Many other New England towns also use metered parking.
• Expect paid or limited lots near popular beaches and tourist attractions. If you don’t mind walking, you can usually find free street parking further away.
• If you plan to include Acadia in your itinerary: Parking is free at Acadia National Park’s visitor centers, with a free shuttle you can then hop on to explore the park. I definitely recommend this option over driving inside the park, especially if you’re going during high season, as there’s tons of traffic and it can be hard to find parking near the most popular scenic points.

Car rental

Unless you’re planning to drive your own car in New England, I highly recommend renting a car vs. trying to use public transportation. You’ll have so much more freedom and flexibility.

➡️ Find the best rental car through DiscoverCars 🚗

What to book in advance

While there’s nothing I love more than taking it easy during a road trip and leaving things open to spontaneous discovery, there are still times where booking specific activities ahead of time makes sense.

Here are a few things you may want to consider reserving in advance:

• Popular restaurants where you want a guaranteed table
• Boat tours and cruises
• Any other guided tours
• Tickets to shows or other reserved events

🌟 RESERVE AHEAD: SOME THOUGHT-STARTERS FOR YOU 🌟

TOP-RATED BOAT TOURS AND CRUISES 🛳
Boston Duck Boat Sightseeing Tour
Newport Sailing on Schooner Adirondack
Portland Sunset Lighthouse Cruise

TOP-RATED GUIDED TOURS 🚶‍♀️
Boston Freedom Trail Walking Tour
Newport Food and History Walking Tour
Portland City and Lighthouse Tour

Extended Itinerary: 10 Days in New England (adds Acadia National Park + Burlington, VT!)

Have even more time to spare? Here’s how I would map out a 10-day New England road trip. Note that most of these places are included in the seven-day itinerary, so scroll back up for details on those repeat destinations. I’ve included my best tips for the *new* additions for this itinerary below!

Day 1: Boston, Massachusetts

Driving time: None! This itinerary assumes you arrive in Boston early and have the full day to explore, then stay overnight here.

Day 2: Newport, Rhode Island

Driving time: 71 miles (roughly 1.5 drive from Boston to Newport)

Day 3: Mystic to Washington, Connecticut

Driving time: 145 miles (roughly 1 hr from Newport to Mystic and 1 hr, 45 minutes from Mystic to Washington)

Day 4: Stockbridge, Massachusetts to Killington, Vermont

Driving time: 176 miles (roughly 1 hr, 20 min from Washington to Stockbridge and 2.5 hours from Stockbridge to Killington)

Day 5: Stowe to Burlington, Vermont

Driving time: 110 miles (roughly 1 hr, 30 min drive from Killington to Stowe, 45 min from Stowe to Burlington)

Drive from Killington to Stowe first thing in the morning and spend the first half of the day exploring the popular ski town.

With just a few hours, I’d recommend spending part of the time browsing the shops downtown and then going on a moderate hike, such as Stowe Pinnacle via Pinnacle Meadow Trail.

In the afternoon, you can head up to Burlington, which is only about 35 miles north of Stowe.

Burlington is the largest city in Vermont, with a fun, artsy vibe and a great food and shopping scene. It’s nestled along Lake Champlain, Vermont and New England’s largest lake that shares borders with New York and Quebec, Canada.

Best things to do in Burlington:

• Enjoy Waterfront Park and the Burlington Greenway for gorgeous Lake Champlain views
• Explore Church Street Marketplace for great food and shopping
• Take a Spirit of Ethan Allen cruise on Lake Champlain
• Grab some Ben & Jerry’s ice cream. The company was founded here!

Where to stay in Burlington

📍Hotel Vermont: A popular boutique hotel conveniently located near the downtown shops and restaurants.

📍Cozy Airbnb: This is where I stayed during my Burlington trip — a simple, cozy room within close driving distance to downtown.

💡Want more Burlington tips? I’ve written a detailed post here.

Day 6: White Mountains, New Hampshire

Driving time: 136 miles (roughly 2 hr, 10 min from Burlington to Lincoln, NH and about 1 hour (with no stops) to drive the Kancamagus Highway to Conway)

Days 7-8: Bar Harbor and Acadia National Park, Maine

Driving time: 194 miles (roughly 4 hours from Conway, NH to Bar Harbor)

I didn’t include Bar Harbor and Acadia National Park in my 7-day New England itinerary because it’s a bit too far north, but if you have 10 days, this “crown jewel of the North Atlantic coast” is an absolute must-see.

Bar Harbor is literally right next to Acadia and it’s the perfect “base camp” to explore all of its beauty. The town itself is worth spending some time in — lots of shops and restaurants, but also incredible views of Frenchman Bay.

Must-try places in Bar Harbor:

• Jordan’s Restaurant, known for its Maine blueberry pancakes
• Mount Desert Island Ice Cream for its eclectic flavor combinations
• Lobster Pound for what I believe is the best lobster roll I’ve ever had (their house garlic aioli sauce is amazing)

Some of my favorite things to do at Acadia National Park:

• Reserve a time slot on Recreation.gov to take in the mesmerizing views at the summit of Cadillac Mountain.
  • Note: The Cadillac Mountain Summit Road requires timed entry from May through October. Reserve a slot at recreation.gov before you go.
• Relax on one of Maine’s only sandy beaches, aptly named “Sand Beach” and walk along the jagged coastline on the Ocean Path Trail.
• Hike around Jordan’s Pond and try the famous tea and popovers at Jordan’s Pond House Restaurant.

Where to stay in Bar Harbor

📍Coach Stop Inn: A super cute bed-and-breakfast about a 15-minute drive from downtown Bar Harbor.

📍Bar Harbor Inn & Spa: A great option if you want to be right downtown and close to all the shops and views.

⛰ Check out this post for even more ideas on what to do at Acadia National Park!

Days 9-10: Portland, Maine to Portsmouth, New Hampshire and back to Boston

Driving time: 268 miles (roughly 3 hours from Bar Harbor to Portland, 1 hour from Portland to Portsmouth, and 1 hour from Portsmouth to Boston)

On Day 9, drive from Bar Harbor to Portland and spend the afternoon exploring there.

On Day 10, drive from Portland to Portsmouth and spend some time there before slowly meandering back down to Boston.

Note: If you’re still up for more exploration, consider a quick stop in Marblehead, MA on your way down from Portsmouth, before going back to Boston. Climb the rocks at Castle Rock for one of my favorite viewpoints in New England. Downtown Marblehead is also really cute.

Shorter Version: 5 Days in New England

Don’t have a full week to spend in New England? Not to worry. You can still cover a lot of ground in fewer days. Here’s a recommended five-day itinerary for you.

Note: This itinerary is a bit ambitious and assumes you really enjoy a good road trip and don’t mind being in the car for a few hours most days (with driving time split between different locations). If you don’t want to do that much driving, you could cut a couple destinations and go at a more relaxed pace.

🌟 One of the things I love most about traveling in New England is how relatively close a lot of destinations are. You can see a lot of amazing sites within a short period of time. This, coming from someone who grew up in the Midwest, where you can spend an entire day driving from one part of a state to another. 🙃

Day 1: Boston, Massachusetts

Driving time: None! This itinerary assumes you arrive in Boston early and have the full day to explore, then stay overnight here.

Day 2: Newport, Rhode Island to Mystic, Connecticut

Driving time: 118 miles (roughly 1 hr, 30 min drive from Boston to Newport and 1 hr, 10 min drive from Newport to Mystic)

Spend the first half of the day exploring Newport before driving further west to Mystic for the rest of the day.

Day 3: Killington and Stowe, Vermont

Driving time: 283 miles (3 hr, 40 min drive from Mystic to Killington, 1.5 hr from Killington to Stowe)

Leave early in the morning to drive from Mystic to Killington, and spend a few hours there before driving up to Stowe and staying the night there.

Day 4: White Mountains, New Hampshire

Driving time: 126 miles (roughly 2 hr from Stowe to Lincoln, NH and about 1 hour (with no stops) to drive the Kancamagus Highway to Conway)

Day 5: Portland, Maine to Portsmouth, New Hampshire and back to Boston

Driving time: 168 miles (roughly 1.5 hours from North Conway to Portland, 1 hour from Portland to Portsmouth, and 1 hour from Portsmouth to Boston)

Other Must-See Places in New England

Okay, we’re getting crazy now, BUT if you have even more than 10 days to travel around New England, here are some of my other all-time favorite places.

Fair warning: I’ve spent a LOT of time in New England and still feel like there are endless places to explore. You’ll never run out of things to see and do, but I’m trying my best to help you narrow down the list. 🙂

Ogunquit, Maine

Ogunquit is a popular destination here in New England but not as well-known in other parts of the U.S. It’s one of the first towns after crossing the border into Maine, and it has a lot of fun things to do.

• Ogunquit Beach Lobster House: Not far from Ogunquit Beach, this restaurant serves amazing seafood. This is the place where I first fell in love with lobster rolls.
  
• Ogunquit Beach: This family-friendly beach is especially popular in the summer as it’s a large beach and there are many shops and restaurants nearby.
  
• Perkins Cove: Browse through this cluster of shops and restaurants in traditional New England architecture. Be sure to stop at the Corner Cafe for delicious Maine blueberry pie ice cream!
  
• Marginal Way: Near Perkins Cove is Marginal Way, a 1.25-mile trail with ocean panoramas the entire way. It gives the Cliff Walk in Newport, RI a run for its money.
  

How to incorporate Ogunquit into your New England itinerary:

After visiting Portland, Maine, you could go to Ogunquit instead of visiting Portsmouth, New Hampshire. Or consider visiting both Ogunquit and Portsmouth, either on the same day or on their own dedicated days. It all depends on if you like to keep things fast-paced or spend a little more time in each place.

Salem, Massachusetts

Salem is best known as the location of the Salem Witch Trials in 1692. If you are curious about the town’s dark past, visit the Salem Witch Museum, Salem Witch Trials Memorial, and Old Burying Point Cemetery. Unsurprisingly, Salem is especially popular to visit during the Halloween season.

The House of Seven Gables, made famous by Nathaniel Hawthorne’s 1861 novel with the same name, is also located in Salem and worth a tour.

How to incorporate Salem into your New England itinerary:

Stay an extra day in Boston and visit Salem as a day trip. Salem is only about 25 miles north of Boston. You could also visit Salem after Portland/Portsmouth in the itineraries above, before heading back to Boston at the end of your journey.

Cape Cod, Massachusetts

For beautiful New England architecture, bright and blossoming hydrangeas, and some of Massachusetts’ best beaches, visit the state’s iconic curved peninsula, Cape Cod. It’s one of Massachusetts’ most popular destinations, and with good reason.

🙇🏻‍♀️ I was actually really torn about whether to include Cape Cod as part of this road trip itinerary, because it really is one of my favorite places in New England. But I also feel like Cape Cod (along with Nantucket and Martha’s Vineyard) almost deserves its own dedicated trip, which is why it didn’t make the final cut. All that to say: It’s definitely a must-see if you want to include it in your plan!

Cape Cod is busiest in the summer months when New Englanders and out-of-towners flock to the beaches. If swimming isn’t your #1 priority, you might choose to visit in the spring or fall instead.

Coast Guard Beach is one of the best beaches on Cape Cod, but Keyes Memorial Beach is also a good option. If you have time to drive all the way to the tip of Cape Cod, the town of Provincetown is known for its art galleries and delicious restaurants.

How to incorporate Cape Cod into your New England itinerary:

The start of the Cape is just a little over an hour from Boston, so this could be the perfect destination to tack onto the beginning or end of this road trip itinerary. (Maybe after a week or more of road tripping, spending a few extra days at the beach is just the thing you need!)

Martha’s Vineyard or Nantucket, Massachusetts

And finally, I would be remiss if I didn’t mention Martha’s Vineyard or Nantucket as potential destinations.

In many ways, these iconic islands represent what people traditionally associate with New England: wind-weathered, shingled homes, harbors filled with sailboats and seagulls, and quaint shops and restaurants. A visit to one of these islands will make you feel like you escaped to another world.

How to incorporate these islands into your New England itinerary:

I recommend visiting Cape Cod and one or both of the islands at the same time, as one of the best ferry options to the islands departs from Hyannis or Woods Hole on Cape Cod.

The ferry ride from Hyannis to Nantucket is roughly one hour, and from Woods Hole to Martha’s Vineyard is about 45 minutes.

FAQs

Here are answers to some common questions about New England.

When is the best time to visit New England?

This all depends on what interests you most! New England is beautiful any time of the year, but winter is the most unpredictable in terms of weather. It’s not uncommon for there to be large snow storms that make travel conditions especially difficult.

Unless you are going with the intention of skiing in Stowe and doing other winter activities, you may want to avoid a road trip to New England from December to mid-March.

Do you enjoy exploring in the winter? Check out Massachusetts in Winter: Things to Do, Places to Visit, and More.

Spring is beautiful in New England with all the blossoming trees, but expect a little more rain than usual from March to June. Some hiking trails might still be muddy from the rain and melting snow.

New England summers are really nice, with warm temperatures that are typically not overbearing and lots of sunny days. July to September is when spending time at the beaches and lakes is the most enjoyable.

Of course, New England attracts lots of tourists in the fall because of the colorful foliage. What’s also great about this time of year is the temperatures are a bit cooler but still pleasant enough for hiking and sightseeing.

When is the best time to see fall foliage?

This can be tricky to say, depending on which part of New England you visit and what the weather is like.

For example, in 2022, we visited the White Mountains of New Hampshire in mid-October and already missed the peak period for colorful foliage. At the same time, the leaves were only just beginning to change color in Boston.

For northern New England states, including Vermont, New Hampshire and Maine, the end of September to the beginning of October will likely be the best time to see the fall colors.

For southern New England, including Massachusetts, Connecticut, and Rhode Island, peak season will likely be a bit later, from the beginning of October to early November.

For some of the best fall foliage sightseeing in New England, check out 10 Best Stops on the Kancamagus Highway, New Hampshire.

How many days do I need in New England? Is 7 days enough?

As you have probably gathered from this post, there is A LOT to see in New England. At a minimum, I recommend spending an entire week in this region to get a taste of all six New England states.

However, if you have a little more time to spare, two weeks would allow you to tack on additional destinations not included in this 7-day road trip, such as Cape Cod or Acadia National Park.

How many miles does this 7-day itinerary cover?

This itinerary covers 755 miles, an average of 108 miles per day (close to two hours of driving time).

A couple days have a bit more driving than others:

• Day 3: Newport to Mystic, and then Mystic to Washington = 145 miles or around 3 hours of driving
• Day 4: Stockbridge to Killington = 122 miles, or about 2.5 hours of driving

Generally, I tried to space out the amount of driving fairly evenly, but this itinerary is definitely a true road trip: Lots of time on the road. 🙂

Is New England expensive?

This varies based on what time of year you go and what activities you want to do. Generally, costs in New England are a bit higher than other parts of the U.S. but as with any trip, there are ways to spend more money and ways to save.

For example, if you plan to spend the majority of your time hiking and walking outdoors, your trip will not be nearly as expensive as if you book a lot of special tours and activities or often dine in restaurants.

Tourism in New England is highest in the summer and fall, so hotel costs will likely climb during these seasons.

Can you do this road trip without a car?

I personally would much prefer bringing my own car or renting a car to tackle this road trip itinerary. While you could find a train or bus to take you to each location, it would require a lot of switching between vehicles, figuring out time tables, etc.

I love the flexibility of having a car and getting to stop whenever I want. While I’ve tried to map out key stops throughout New England, part of the fun of.a road trip is stumbling across things that aren’t part of your plan.

Having a car allows room for spontaneity, whereas using other forms of transportation will box you in.

Conclusion

New England is such a historic and beautiful part of the country, with something for everyone to enjoy. To recap, here is a quick summary of this 7-day New England road trip:

• Day 1: Boston, Massachusetts
• Day 2: Newport, Rhode Island
• Day 3: Mystic to Washington, Connecticut
• Day 4: Stockbridge, Massachusetts to Killington, Vermont
• Day 5: Stowe, Vermont
• Day 6: White Mountains, New Hampshire
• Day 7: Portland, Maine to Portsmouth, New Hampshire

If you’ve determined that New England is too awesome to limit your visit to just one week, here are some great add-ons:

• Acadia National Park, Maine (after White Mountains)
• Ogunquit, Maine (after Portland)
• Salem, Massachusetts (after Boston or Portsmouth)
• Cape Cod, Massachusetts (tack on at the end of this itinerary)
• Martha’s Vineyard or Nantucket, Massachusetts (tack on at the end of this itinerary)
• Lake Champlain, Vermont (after Stowe)

Have a fabulous time!

PLANNING A TRIP?
These are the resources I recommend:
✈️ Flights: Skyscanner
🛌 Hotels: Booking.com
​🚗 Rental cars: DiscoverCars
🎟 Tours: Viator or GetYourGuide