The Perfect 7-Day New England Road Trip from Boston (2025)
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.
Now that I’ve lived in New England for five years, I have a better understanding of 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!
⏰ SHORT ON TIME?
🛌 DESTINATIONS + WHERE TO STAY
Boston, Massachusetts: Hyatt Regency Boston Harbor
Newport, Rhode Island: Hotel Viking
Mystic to Washington, Connecticut: Mayflower Inn & Spa
Stockbridge, Massachusetts to Killington, Vermont: Mountain Meadows Lodge
Stowe, Vermont: Trapp Family Lodge
White Mountains, New Hampshire: New England Inn & Lodge
Portland, Maine and Portsmouth, New Hampshire: Hampton Inn & Suites
🚗 NEED A CAR?
Book through Discover Cars for some of the best rates
New England Road Trip for 7 Days
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 into New Hampshire and Maine, and then back down to Boston.
Day 1: Boston, Massachusetts
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
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
📍America’s Cup Inn: A small hotel within easy walking distance of most downtown Newport attractions. Each room is uniquely decorated with antique, colonial furnishings.
📍Hotel Viking: On the list of Historic Hotels of America, this hotel is full of character and charm.
Day 3: Mystic to Washington, Connecticut
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 Washington
📍A Whimsical Cottage: This cozy vacation home will give you a more local experience of Washington.
📍Mayflower Inn & Spa: If you’re a Gilmore Girls fan, this luxurious hotel will be especially meaningful, as it’s said to have inspired the Independence Inn on the show.
Day 4: Stockbridge, Massachusetts to Killington, Vermont
Start your day with breakfast at the Po Cafe in Washington before heading 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 a little over two 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
On day 5 of this 7-day New England road trip, you will visit the magical town of Stowe, Vermont.
About an hour and 20 minutes 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
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 and Portsmouth, New Hampshire
On the last day of this 7-day New England road trip, head 1.5 hours 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.
New Castle is less than an hour from Boston, where you can return on Day 8 to end your epic New England road trip!
New England 7-Day Road Trip Map
More Places to Add to Your Itinerary
If you want to extend your trip beyond a week (I would not blame you one bit), here are a few other places to add to your itinerary!
Acadia National Park, Maine
The crown jewel of the North Atlantic coast, Acadia National Park is an absolute must-see. I didn’t include it in this 7-day New England itinerary because it’s a bit too far north, but if you have a few more days to spare, you won’t regret a visit here.
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 is only open from around April to October).
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.
And of course, you must pay a visit to the picturesque town of Bar Harbor, right next to Acadia National Park. Jordan’s Restaurant is known for its amazing blueberry pancakes, and Mount Desert Island Ice Cream serves some of the most interesting flavors.
How to incorporate Acadia National Park into your New England itinerary:
Acadia National Park would naturally fit after Day 6 in this itinerary, but you would want to give yourself at least three extra days to drive up there and fully explore the region before heading south to Portland.
Ogunquit, Maine
Ogunquit is a popular destination here in New England but not as well-known in other parts of the USA. 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:
You could swap Portsmouth, NH with Ogunquit, ME on Day 7 and visit Portsmouth on Day 8, OR dedicate an entire day to Portland, ME and spend Day 8 in Ogunquit and Portsmouth.
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.
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.
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:
Extend this 7-day itinerary by another day or two (or longer, if you plan to visit Martha’s Vineyard or Nantucket as well!).
Martha’s Vineyard or Nantucket, Massachusetts
In many ways, the iconic islands of Martha’s Vineyard and Nantucket 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.
Lake Champlain and Burlington, Vermont
Lake Champlain is Vermont and New England’s largest lake, which is also shared with New York and Quebec, Canada. There are plenty of things to do on and around the lake, including boating, kayaking, swimming, shopping, dining, and more.
Burlington is the largest city in Vermont and is nestled right along Lake Champlain. It’s a hip, artsy town with an awesome food and shopping scene.
How to incorporate Lake Champlain into your New England itinerary:
An extra day or two to visit Lake Champlain and Burlington could be sandwiched between Days 5 and 6 in this New England itinerary.
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 where we live.
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?
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.
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.
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, Rhode Island 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 (between Days 6 and 7)
- Ogunquit, Maine (on or after Day 7)
- Salem, Massachusetts (between Days 1 and 2 or after Day 7)
- Cape Cod, Massachusetts (after Day 7)
- Martha’s Vineyard or Nantucket, Massachusetts (after Day 7)
- Lake Champlain, Vermont (between Days 5 and 6)
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
