The Best New England Road Trip Itinerary

Coastal cities, mountain resorts, autumn leaves, fresh clam chowder. Are we describing your dream vacation? If so, look no further than a New England road trip.

As the first region colonized in America by English settlers in the 17th century, New England has an enriching history and some of the most stunningly diverse geography in the country. Choosing just one New England destination is more than a bit challenging.

The best New England road trip covers all six states––Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont. From historic lighthouses that line rocky shores to ski slopes filled with knee-deep powder, you will be amazed by all that New England has to offer.

Let’s begin our New England journey.

Start Your Engines in Boston

As the biggest city in this region and home to a major airport, Boston is the ideal starting point for your adventure. Boston also happens to be heaven on Earth for history buffs, foodies, artists, and sports fanatics alike.

One of Beantown’s many must-see attractions is Boston Tea Party Ships and Museum. Here, you can relive the event that transformed American history by throwing crates of tea off replica 18th century vessels. 

Walking along the Freedom Trail is also a must. The 2.5-mile stretch encompasses 16 areas of historical significance, including the Boston Common, Paul Revere House, the USS Constitution, Old South Meeting House, and the site of the Boston Massacre.

Once you’ve gotten your dose of colonial America, indulge in Boston culture by catching a game at Fenway Park. Home to the Red Sox since 1912, this historic stadium is the oldest active ballpark in Major League Baseball. 

For a picturesque night out, take a stroll in Boston’s quaint Beacon Hill, lined with narrow cobblestone streets, federal-style row houses, and gaslit street lamps. This homey neighborhood is home to many boutique shops and delicious eateries. 

Drive to the Ocean State

Once you’ve had your fill of Boston, make the drive over to its smallest state – Rhode Island. Rhode Island is only 1,200 square miles in total area, but it has more than 400 miles of beautiful serene coastline.

Strolling Newport’s Cliff Walk is one of the best ways to experience Rhode Island. This easy 3.5-mile hike hugs the rugged coastline that Rhode Island is known for. You’ll find peace as you breathe in the fresh ocean air and listen to the waves slowly lap against the rocky shores.

Along this walk, you can also catch a glimpse of Rhode Island’s opulent gilded-age mansions. One such estate is The Breakers, a 70-room mansion with more than 62,000 square feet of living space and a total area of 125,000 square feet. Built for Cornelius Vanderbilt II, this National Historic Landmark is now open to the public.

A trip to Rhode Island would not be complete without visiting Bowen’s Wharf, where you can enjoy fresh seafood and hot chocolate before a vast ocean view.

Cruise Through Scenic Connecticut  

If you’re traveling in the fall, you will be amazed by the red-orange forests that populate this beautiful state. Litchfield Hills – a geographic region in Northwest Connecticut encompassing more than a dozen towns and cities – has no shortage of that. This hidden gem offers a variety of outdoor activities, including hiking, canoeing, and fishing. 

Another notable stop is the scenic seaside town of Mystic. Here, you can explore the historic Mystic Seaport. Tour America’s oldest commercial ship and the last wooden whaleship in the world. After walking through a recreated 19th-century coastal village and working shipyard, you can get a bite and browse the shops in the quaint downtown area.

Take Another Stop in Massachusetts

Your route will take you to the unique town of Lenox, Massachusetts. The center of the Berkshires of Massachusetts, this lovely town combines both nature and culture.

In the summertime, you can enjoy concerts from top symphonies and folk artists like James Taylor. You can also take in live theatre at the world-renowned Shakespeare and Company.

Between picturesque hikes of the vastly forested Berkshire region, check out even more Gilded Age mansions. One notable mansion in this area is the Mount, Edith Wharton’s turn-of-the-century estate––a must-see for literature lovers. Lenox is also home to the Ventfort Hall Mansion and Gilded Age Museum, a 1890s mansion open for tours.

Take in Vermont’s Scenery

As you drive through scenic Route 7, you will end up in Vermont’s biggest city, Burlington. Here, you will find a variety of boutique shops, book stores, and restaurants. You’d be remiss not to indulge in some of Vermont’s famous maple syrup.

Burlington also overlooks the shimmering Lake Champlain. Join in on such lake-centric activities as sailing, stand-up paddleboarding, or a ferry ride over to upstate New York. You can also rent bikes and cruise along the Burlington Bike Path, which hugs the lake’s perimeter.

You will then head up the scenic Route 100 to get to Stowe, Vermont. The first true mountain town on your road trip, Stowe epitomizes the beauty synonymous with Vermont. In addition to a smattering of hikes throughout its surrounding mountains, you can also find a white-steepled church, old-timey general store, and 50’s style diner. This quaint town feels like a time capsule.

Stowe is home to some of the best East Coast skiing and is worth a stop if you’re traveling during the winter. There are few other places in the country with the deep, airy powder of Vermont’s mountains.

Hike Through the Mountains of New Hampshire

If you were impressed by Vermont’s mountains, you’d feel right at home in New Hampshire. The next stop along your journey in North Conway, home to the tallest mountain range in New England––the White Mountains.

Needless to say, this region offers the best hiking that you will find on your trip. In Franconia Notch State Park, you can visit the Basin, a natural granite pool carved out by the flow of a waterfall. The nearby Flume Gorge is a narrow ravine that you can cross via a boardwalk at its base.

You’re sure to fall in love with the variety of mountain towns in this area. Conway is home to a lovely array of shopping, restaurants, and outdoor activities such as paddle boarding and river tubing. Over in Barlett, you can dip into Diana’s Baths, a stunning area of cascading waterfalls and pools.

One of the parts of this entire road trip will be driving the Kancamagus Highway. This 26-mile stretch winds through one of the lushest forests in New England. The drive is even more picturesque in the fall when the surrounding trees turn red, yellow, and orange.

End Your Adventure in Maine

As the East Coast’s northernmost point, Maine has over 3,400 miles of coastline. One of your first stops will be Ogunquit, a picturesque town that’s home to over three miles of white-sand beaches. Indulge in world-renowned Maine Lobster at the Perkins Cove harbor.

As you drive north to Portland, stop at Cape Elizabeth, home to the storied Portland Head Light, a lighthouse built in 1791. In Portland, you can enjoy the working fish wharves, quaint shops, and the gallery walk of this seaside town. 

Continue traveling north to Georgetown and Rockland, where you can enjoy even more coastline and lobster. After over 230 miles, you will reach Acadia National Park. In addition to some 45 miles of bike trails, Acadia offers the best hiking in the northeast. 

One of our favorite trails is Thunder Hole, a small inlet in Acadia’s unrivaled coastline where waves crash against the rocks, creating a booming sound and spraying water up to 40 feet in the air. For a more serene vibe, check out South Bubble, where you can achieve an unmatched view of the still Jordan Pond and season-changing East Coast trees.

The Drive Back 

While you can make the drive back to Boston in just over four hours, you can also take the scenic route, which we always recommend at HearHere. 

As you head down south, make a stop in Portsmouth, New Hampshire. This beautiful seaside town has a vintage vibe that you can spend hours exploring. If you haven’t yet, take a chance to watch a New England sunset. The orange sun beaming off the crystal clear water is truly awe-inspiring.

Another noteworthy stop is the infamously historic Salem, Massachusetts. Whether you’re a history buff or enjoy a good spook, you’ll want to tour the various sites of the Salem Witch Trials. To kick it up a notch, partake in a frightening night-tour of these tragic events.

By the time you get back to Boston, you’ll have experienced one of the stunning journeys available in the United States.

Explore New England With HearHere

Are you looking for something to listen to on your next road trip to New England? Download HearHere and discover what makes New England a unique destination for outdoor enthusiasts and history buffs alike. We curate content based on your interests – from sports to history to local culture – and package it into a high-quality “road trip companion” you can access at any time, so you don’t miss a thing.

Check out HearHere today. The world is waiting for you. 

Sources: 

These Are the Best Road Trips in New England | BestLifeOnline.com

Tips for Walking the Freedom Trail in Boston | EarthTrekkers.com

25 Best Things to Do in Mystic, Connecticut | VacationIdea.com

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