Experience The Best Of New England In 7 Days: A Road Trip Itinerary

EPIC New England Road Trip Guide (BEST DESTINATIONS IN 2021)

New England has some of the most diverse, beautiful, and historic destinations in the United States. From the rocky Atlantic coast to the rolling hills of Vermont and New Hampshire, this region is full of unique experiences that can only be found here. If you have seven days to explore New England, here’s a road trip itinerary to help you make the most of your time and see the best of this area.

Day 1: Boston, Massachusetts

Start your trip in Boston, the largest city in the region and home to some of the oldest, most iconic landmarks in the United States. Spend the morning walking the Freedom Trail, a 2.5-mile route that takes you to 16 historically significant sites, including the Paul Revere House, the Old North Church, and the USS Constitution Museum. In the afternoon, take a stroll along the Charles River Esplanade, a scenic path along the banks of the Charles River, and end your day with a visit to Fenway Park, the home of the iconic Boston Red Sox.

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Day 2: Portland, Maine

On day two, make your way up the coast to Portland, Maine. This quintessential New England port city is full of quaint cobblestone streets, historic lighthouses, and delicious seafood. Spend the morning exploring the Portland Head Light, one of the oldest lighthouses in the United States, and walking through the city’s cobblestone streets. In the afternoon, take a boat tour of Casco Bay and see the many islands that dot the coast. End your day with a meal at one of Portland’s renowned seafood restaurants.

Day 3: White Mountains, New Hampshire

On day three, head north to the White Mountains of New Hampshire. This rugged mountain range is home to a wealth of outdoor activities, including hiking, camping, skiing, and snowmobiling. Spend the morning exploring the Franconia Notch State Park. Take a scenic drive along the Kancamagus Highway and stop at the many overlooks to take in the stunning views of the mountains. In the afternoon, drive up to the summit of Mount Washington, the highest peak in the northeast, and take a scenic chairlift ride to the peak.

Day 4: Woodstock, Vermont

On day four, travel to the picturesque town of Woodstock, Vermont. This charming village is full of charming homes, covered bridges, and rolling hills. Spend the morning exploring the Marsh-Billings-Rockefeller National Historic Park, which offers miles of hiking trails and impressive views of the surrounding landscape. In the afternoon, visit the Billings Farm and Museum, which offers a glimpse into 19th century Vermont life. End your day with a visit to the Woodstock Inn and Brewery, a historic inn and brewery located in the center of town.

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Day 5: Plymouth, Massachusetts

On day five, make your way back down the coast to Plymouth, Massachusetts. This small town is full of history, as it was the site of the first permanent English settlement in the New World. Spend the morning exploring the Plymouth Plantation, a living history museum that recreates the life of the original settlers. In the afternoon, take a day trip to nearby Cape Cod and visit the famous lighthouses and pristine beaches. End your day with a stroll through the town’s historic downtown and grab a bite to eat at one of the many restaurants.

Day 6: Newport, Rhode Island

On day six, travel to Newport, Rhode Island. This charming coastal town is full of history and culture. Spend the morning exploring the many historic mansions, including the Breakers, Rosecliff, and Marble House. In the afternoon, take a boat tour of the harbor and see the many quaint islands that dot the coast. End your day with a visit to one of the many art galleries and restaurants in town.

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Day 7: Hartford, Connecticut

On your final day, make your way to Hartford, Connecticut. This small city is home to some of the most notable sites in the region. Spend the morning exploring the Mark Twain House and Museum, which is housed in the former home of the famed author. In the afternoon, take a stroll through Bushnell Park and visit the Connecticut State Capitol Building. End your day with a visit to the Wadsworth Atheneum Museum of Art, the oldest public art museum in the United States.


New England is full of unique, historic, and beautiful destinations that are perfect for a road trip. This seven-day itinerary will take you to some of the most iconic sites in the region, and you’ll have plenty of time to explore each destination. From Boston to Hartford, and everywhere in between, this road trip will give you an unforgettable experience and a true appreciation for the beauty of New England.