The Ultimate New England Road Trip

January 31 2022, 9:31pm

Pack up the car because it’s time to hit the road once again in New England. You’re about to discover one of America’s most charming regions, where the lush mountainous regions covered in colorful fall foliage extend towards the scenic rocky coastline. Here, past meets the present as you explore sites of early American history and settlements. Even driving in-between stops is filled with beautiful sights and sleepy towns.

We’ll help you prepare for the ultimate New England road trip with exciting stops in each state. Completing the entire road trip itinerary will take approximately two weeks, but you can always personalize the itinerary when you begin planning a new England road trip.

So, when you’re ready, start your engines and let’s go to New England!

Boston to Cape Cod – 70 miles

boston skyline

The journey from Boston to Cape Cod will be your first glimpse at the beautiful coast lining the region. And while there is a ferry that crosses Cape Cod Bay, why miss out on taking the scenic route? Traveling along MA-3 S, you’ll reach a few interesting places en route to the cape. So, if you’re in no rush to get to the beach, take a few hours to detour to a few of the top sights.

Arriving in Plymouth is like traveling in time where you’ll discover the origins of America. This site was home to the first settlement in the country after the pilgrims arrived at the ‘New Land.’ History comes alive at the Plimoth Patuxet Museums, whose 17th-century village recreates life in colonial times. Costumed actors reimagine the lifestyle of pilgrims, and it’s even the site of the landmark Plymouth Rock. In addition, artifacts exhibited in the Pilgrim Hall Museum provide evidence of the early settlement.

Several quaint seaside towns line Cape Cod. Hyannis is one of the most famous towns you’ll drive through on this road trip. It’s a town that’s attracted the likes of former President John F. Kennedy and his family for frequent vacations. The John F. Kennedy Hyannis Museum exhibits archives about his experiences on the cape while the lush gardens surrounding the John F. Kennedy Memorial were dedicated in his honor. Before leaving town, go for a walk down Main Street, where boutique shops, bars, and restaurants line the strip.

Provincetown is the tip of Cape Cod. It’s where the picturesque Race Point Lighthouse stands 45-ft tall illuminating the entrance to Cape Cod Bay. Enjoy views of the lighthouse while relaxing on Race Point Beach, one of the best beaches on Cape Cod. Head into the artsy downtown area, where charming galleries and shops showcase the talents of local artists.

Cape Cod to Rhode Island – 76 miles

rhode island

It’s time to say goodbye to Massachusetts because you’ll soon cross over the Rhode Island State Line. Rhode Island is the smallest state in the US but packs a big punch when it comes to fun things to do on your New England road trip. Visit a few of the popular cities in Rhode Island to see the best that it has to offer.

Driving on I-195 W will take you directly to Providence, the capital of Rhode Island. Providence is a significant contrast to the small coastal towns. This giant metropolis is a hub for political and cultural activity and can easily take a few days to explore. 

Admire the stately Rhode Island Capitol Building sitting prominently on a hill with free tours offered inside. Next, head to the Brown University Campus to see the historical buildings and lecture halls preserving its IV league reputation. The art scene is lively, with venues like the RISD Museum showcasing works of American art and the WaterFire public art installation burning in Waterplace Park.

Drive down to Bristol, sitting on the coast that was a magnet for wealthy Rhode Islanders. First, tour the stunning Blithewold Mansion, with views of the coast from its manicured gardens and over 300 floral species in the arboretum. Then, head to Linden Place, a house museum set in one of Bristol’s most extravagant estates.

After a short stop in Bristol, Newport is next up. This port town has become a popular tourist destination when driving through Rhode Island. It’s most famous for the Gilded Age Vanderbilt mansions lining the coast, showing us just how lavish the other side lived. Go for a stroll on the Cliff Walk, where you’ll pass by The Breakers, The Elms, Marble House, and other opulent mansions open to the public for tours.

Rhode Island to Connecticut – 100+ miles

yale university

Grab some snacks as you leave Newport because there are approximately 100 miles before you reach your next destination: New Haven. Seeing the ‘Welcome to Connecticut’ sign while traveling along I-95 S means that you can check yet another state off your bucket list during this Ultimate New England road trip.

New Haven is located near Connecticut’s southern coast. Take in sights of the sea while checking out Lighthouse Point Park. The tall, white lighthouse casts a shadow over the sandy beaches where you can enjoy a mid-trip picnic and go for a refreshing swim. Dry off, then drive into the city, home of Yale University. Gothic architecture surrounds the campus of this prestigious educational institution with landmarks like the Harkness Tower or discovering art masterpieces from Rubens and Rothko inside the Yale University Art Gallery.

Continue north, where you’ll encounter Connecticut’s mountainous region nearby the city of Meridan. It’s time to enjoy outdoor recreation because there are lots to explore in this diverse landscape region. Venture beneath the canopies of the woodlands covering Hubbard Park to see natural landmarks like Mirror Lake. Or uncovering the mesmerizing cascading falls hidden within the Wadsworth Falls State Park. Challenge yourself with a hike to the summit of Chauncey Peak or go skiing in the winter at Powder Ridge Mountain Park.

These picturesque nature sights transform into a large metropolitan area as you approach Hartford, the capital of Connecticut. The glimmering golden dome of the Connecticut State Capitol Building shining above Bushnell Park makes it one of the most beautiful capitals in the US. Immerse in the local cultural heritage by retracing the steps of famed authors at the Mark Twain House and Museum and Harriet Beecher Stowe Center. And to escape the busy city streets, retreat to Riverside Park for a picnic or scenic stroll on the riverbanks.

Connecticut to Vermont – 200+ miles

vermont

The beautiful natural landscape of Massachusetts unfolds before you as you bypass it on the way between Connecticut and Vermont. Enjoy views of the scenic drive while cruising along I-91 North.

See how Vermont earns its nickname as the ‘Green Mountain State’ when visiting the Green Mountain National Forest. The route leads directly into these mountainous woodlands, where you can enjoy a range of recreational activities. During the summer, explore the forest grounds on a nature trail where moose, coyote, and black bears lurk evasively between the trees. During the winter, ski the famous slopes at Stratton Mountain Resort or Okema Mountain Resort.

Follow the signs directing towards Montpelier as you emerge from the Green Mountain National Forest. Montpelier is the capital of Vermont and a must-visit for any New England road trip. You’ll immediately recognize the shining gold done decorating the Vermont State House, where guided tours reveal impressive artworks housed inside of it. The grassy fields of Hubbard Park are the perfect place to enjoy a leisure day where even pets are allowed to trek the hiking routes. And if you’re feeling hungry, pick up a few fresh produce and veggies at the Capital city Farmers Market.

Veer west from Montpelier, and you’ll soon find yourself in Burlington. A quiet, lakeside townhome to the University of Vermont. Lake Champlain sits passively in front of you as you relax on the Waterfront Park. Rent a couple of bikes and explore the trails winding around the lake. After you’ve admired the views, hop on a Lake Champlain cruise. Then, venture into town and revel in the lively atmosphere at the Church Street Marketplace, where you’ll have lots of dining and entertainment.

Vermont to New Hampshire – 140 miles

new hampshire

Hopefully, you’ve got enough of the New England big city life because New Hampshire will give plenty of lovely sights taking in lush, colorful scenery. Every season reveals a rejuvenated beauty across the state, from its mountain summits to the rugged shores.

White Mountains National Forest greets you soon after crossing into New Hampshire. This vast region of mountains and mixed forests is where you can get active or simply enjoy the sights. Jump on the Mt. Washington Cog Railway for a scenic ride to the top of the highest peak in New Hampshire. Mt. Washington is a popular destination for hiking in the summer and skiing in the winter. If you have the energy, attempt a hike along a section of the iconic Appalachian Trail or retreat to your car to cruise the famous Kancamagus Scenic Drive.

Continue down to the coast where the charming port city of Portsmouth awaits. Docked boats line the harbor as you stroll along the boardwalk. Relive the past when you enter inside Strawbery Banke Museum, one of the largest living museums in the US. It preserves the legacy of New Hampshire’s oldest community, with many of its original 17th and 18th-century buildings restored. Later, frolic through the colorful riverside gardens in Prescott Park.

Get out of town with a day at the lake. Lake Winnipesaukee is the largest lake in New Hampshire. Enjoy the sandy coastline at Weirs Beach, where sunbathers and swimmers flock to when the weather cooperates. If you can splurge a bit on your New England road trip cost, how about renting a yacht to cruise the lake. Views from Castle in the Clouds make you appreciate the lake and the beauty of the Finger Lakes Region.

New Hampshire to Maine – 70 miles

maine

Although we’re nearing the end of our ultimate New England road trip, the good news is that Maine is one of the most exciting states in the region. You’ve survived until now, so get ready for the grand finale because Maine is a stop you don’t want to skip over.

Set your GPS directly to the coast, and you’ll reach Portland in less than two hours. This port town sits on Casco Bay, where the Portland Head Light stands regally at the mouth of the bay. It’s the oldest lighthouse in the state and a popular postcard photo opportunity. Refuel with a taste of the famous lobster roll at Highroller Lobster Co. before indulging in your guilty pleasure with an artisanal-flavored treat from The Holy Donut. Finally, reminisce on the past with a stroll through along the piers of the Old Port District.

It’s a straight stop to Augusta, the capital city, when you hop on I-295 North. Large color-changing trees fill the blocks in the city, making it a scenic destination in any season. A visit to Capitol Park makes sightseeing easy with the Maine State House and governor’s house located onsite. History buffs will enjoy a trip to Old Fort Western with guided tours available of this historic wooden structure built in 1754. Don’t forget to take in the views of the Kennebec River.

Enter the gateway to one of Maine’s most breathtaking regions when you visit Bar Harbor. It attracts many people looking to get away to nature or even whale watching during migration season. Hike to the summit of Cadillac Mountain in Acadia National Park to admire sweeping views of the lush landscape. Explore cliffside trails at Otter Cliff and Ocean Path. Or put on cruise control as you enjoy 27-miles of foliage along Park Loop Road.


Congrats! It’s been a long trip, but you’ve finally made it. We’ve traversed the scenic coastline of Cape Cod and got a taste of the Gilded Age in Newport. From admiring architectural wonders lining the New Haven skyline to exploring natural wonders of the White Mountain National Forest to the outdoor recreation in Acadia National Park, the ultimate New England road trip is complete

Are you planning a New England road trip? Let me know in the comments some of the items on your bucket list to include on the trip!

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