A Guide to the Best New England Road Trip Itinerary

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Stephanie is a cherished member of the Sampling America writing team, dedicated to crafting captivating narratives that transport readers to thrilling adventures across the country and beyond.

Anyone on the East Coast knows New England has something to offer anyone. From white sand beaches to rocky cliffs and pine needle forests, New England makes one of the best road trip locations in the country.

Follow our guide to the ultimate New England road trip itinerary to get the most out of traveling around these historic states.

Boston, Massachusetts

Boston Massachusetts 1
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Beginning your New England trip should obviously begin in the exciting city of Boston, Massachusetts

Boston is a hub of culture, history, architecture, and education. Consider taking a tour of historic Harvard University before visiting one of the city’s many five-star restaurants.  

For outdoor activities, you can hike the scenic Freedom Trail, walk through the historic neighborhood of Beacon Hill, or visit the Boston Common Public Garden. 

Salem, Massachusetts

Salem Massachusetts 1
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Home to the Salem Witch Trials, this city is one of the oldest cities in the country, dating back to the 1600s. Visit the Salem Witch Museum to learn all there is to know about this historic part of United States’ history. 

If you’re lucky enough to drive through New England in the fall, you’ll experience the bustling excitement of the Halloween festivities in Salem. 

Coastal Byway, New Hampshire

New Hampshire
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New Hampshire’s 18-mile coastal highway sits between Main and Massachusetts. Here, you’ll pass by beaches, historic forts and mansions, and many state parks.

Consider stopping in Hampton Beach to walk through the bustling resort town and enjoy the white sand beach and its boardwalk.

York, Maine

York Maine
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Driving through Maine is a quintessential part of a trip to New England. The town of York offers a stunning coastal experience.

If you want to explore nature, get your hiking gear and head to The Marginal Way, a scenic coastal trail in Ogunquit. There will also be plenty of restaurants to try out an authentic Maine lobster roll or an oyster bake.

Portland, Maine

Portland Maine
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Check out the Old Port in the center of the historic town of Portland. Many buildings and roads built hundreds of years ago are still standing.

Portland also has a thriving craft brewery scene, so embrace this old-town attitude and head to the breweries for a pint. You’ll also find some of the world’s best freshly caught lobster and crab here.

White Mountains, New Hampshire

White Mountains New Hampshire
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During the fall season, you’ll see the best foliage in the White Mountains of New Hampshire. Driving, hiking, or even camping in these woods is a recommended experience for anyone who wants to see the best of New England.

If you’d prefer to stay in a hotel with all the amenities, consider the Omni Mount Washington Resort and stay for all the luxurious spa treatments.

Mad River Valley, Vermont

Mad River Valley Vermont
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Mad River Valley sits in the Green Mountains of Vermont. It’s a popular tourist destination for anyone touring New England.

There are several towns here that you can stop in: Duxbury, Fayston, Moretown, and Warren, as well as a few notable ski resorts.

This is the perfect place to rent a cozy cabin in the woods. The lush red Vermont foliage is a stunning background to this vacation, and the outdoor activities are boundless. Enjoy hiking, camping, biking, swimming, and kayaking on the rivers and lakes. 

Burlington, Vermont

Burlington Vermont
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After spending a few days in nature, head to Burlington, Vermont, to experience this quaint, bustling city. Many New Englanders suggest you stop by the Church Street Marketplace for shopping or the Burlington Farmers Market to try local meats and treats.

Burlington sits on the gorgeous Lake Champlain. So take a wander through the town and walk past the harbor.

Block Island, Rhode Island

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Block Island is one of New England’s hidden gems. Many people describe this area as similar to Martha’s Vineyard and Nantucket.

This island is brimming with outdoor adventures and coastal Victorian charm. There are several historic lighthouses, rustic farms, and windswept beaches to walk along.

Newport, Rhode Island

Newport Rhode Island
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Newport was once the home of the rich and the famous. Well-known for Gilded Age Mansions built during the 19th century, Newport is an excellent place to learn about how the wealthy lived in early America.

The Breakers is the most iconic mansion, initially built for the Vanderbilt Family. You can tour this stunning mansion and see the amazing gold-covered walls and hand-painted ceilings.

Cape Cod, Massachusetts

Cape Cod Massachusetts
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Cape Cod is one of the most iconic beaches in America. It’s a place of iconic American scenery and infrastructure with an amazing culinary scene

The quaint Sandwich Village is the oldest town in the cape, dating back to the early 1600s. Many houses, hotels, and B&Bs date back to this time. You can also visit the Heritage Museums & Gardens to learn about the area.

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Miami Beach
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