Escape the Crowds on a Six-State Roundtrip Across New England 

It’s hard to deny, vacationing in New England has an enduring appeal for visitors, no matter what time of year you come. However, despite the appeal of a city break to Boston, if you’re on the hunt to reveal the true extent of New England’s historical towns, magnificent rolling scenery, not to mention its dramatic coastline settings, then we’ve got the perfect vacation itinerary for you. 

Whether you’re wanting an unforgettable family getaway or a solo trip adventure of a lifetime to celebrate America 250, we’ve curated a dream six-state New England road trip that will make you fall in love with the region’s warm hospitality and charm. 

Day 1 & 2 – Plymouth to Seekonk, Massachusetts 

Where better to start our road trip than by heading down to one of America’s most celebrated towns, Plymouth, Massachusetts, famously tied to the country’s early origins dating back more than 400 years. Once you’ve arrived, make sure you spend the afternoon strolling around Plymouth’s historic downtown streets and storybook harbor frontage before settling in for a great night’s sleep at the Best Western Plus Cold Spring to kick start your trip in style.  

Before heading off on the first leg of your New England road trip, be sure to climb aboard one of the ships that started it all, the Mayflower II. Here, this meticulously crafted reconstruction of the original Mayflower ship gives guests a fascinating glimpse into the tight living conditions the Pilgrims endured during their 66-day journey across the Atlantic in 1620. 

Exploring New England’s more recent nautical connections next, we recommend stopping in to survey the incredible war memorial and historic military museum at Battleship Cove in Fall River on route to Seekonk, Massachusetts. Featuring US Naval ships, including the USS Massachusetts and USS Lionfish, Battleship Cove is packed full of outstanding exhibits and makes for an immersive afternoon of discovery before ending the day with a relaxing night’s stay at the Best Western Providence-Seekonk Inn. 

Day 3 – Seekonk to Manchester, Connecticut 

Day three sees us heading into our second New England state on our road trip on a mission to explore the spectacular, ornate National Historic Landmark, better known as The Breakers in Newport, Rhode Island. After a morning wandering around this fabulous building’s elegant halls and admiring its sweeping Atlantic Ocean vistas, we continue along the New England coastline to the seaport town of Mystic, Connecticut. 

After a spot of lunch surrounded by picturesque harbor views, we also suggest paying a visit to the much-loved Mystic Aquarium to meet with some of its resident Beluga Whales, African Penguins, and Sand Tiger Sharks. Afterward, we say goodbye to the New England coastline for a few days as we head north along some of the Constitution State’s beautiful rural highways, making our way to our next rest spot at the Best Western Manchester in Connecticut. 

Day 4 – Manchester to Springfield, Vermont 

Before setting off northwards again, our road trip through New England sees us heading west to spend the morning checking out Wethersfield, also known as ‘Oniontown’ – home to the world-famous Wethersfield red onion. While you’re in town, you can wander around the beautifully preserved homes, tree-lined streets, and centuries-old architecture, and browse the traditional Wethersfield Farmers’ Market held every Thursday between May and October. 

Afterward, the afternoon becomes a tale of two Springfields, as we head north, re-entering Massachusetts briefly for an exciting pilgrimage to the Naismith Basketball Hall of Fame in Springfield, MA. Then, after enjoying the Hall of Fame’s interactive exhibits and roll call of over 450 inductees, we continue north along the stunning Connecticut River Valley before checking in for the night at the Best Western Springfield Hotel in Springfield, Vermont. 

Day 5 – Springfield to Lincoln, New Hampshire 

We kick start our Vermont leg of our six-state road trip tour of New England on day five, heading next to the village of Woodstock to meet with the staff of the family-owned Billings Farm & Museum. Fun for visitors of all ages, this inspirational farm and museum showcases the inner workings of a fully functioning Vermont dairy farm. Not only that, aside from the real-life dairy farm exhibits, Billings Farm & Museum also offers you the chance to jump on a horse-drawn ride or a snowy sleigh ride, depending on what time of year you visit.  

Before you leave Woodstock, we’d also suggest you don’t miss the chance to stroll across the historic Middle Covered Bridge, one of the town’s most iconic postcard-perfect landmarks, which makes for a quintessential Vermont snapshot of your trip. Leaving the Green Mountain State behind, your road trip journey now takes you through the Granite State’s White Mountains before settling down for a cozy night’s sleep at the Woodwards White Mountain Resort, BW Signature Collection in Lincoln, New Hampshire. 

Day 6 – Lincoln to York, Maine 

Undoubtedly, the primary attraction when staying in Lincoln has to be Flume Gorge, an 800-foot-high natural gorge in the heart of New Hampshire’s Franconia Notch State Park. Here, you and your family and friends can walk along the mounted boardwalk that runs along the stream towards the base of Avalanche Falls, the gorge’s very own 45-foot cascading waterfall.  

Leaving New Hampshire behind as we head to our final state on our extraordinary New England road trip, we cruise along the Kancamagus Highway, renowned as one of the best fall foliage roads on the planet. With countless river pulls-offs and mountain overlooks, not to mention a bounty of waterfalls to spot along the way, the Kancamagus Highway illustrates the unspoiled wilderness of the region as we head to our final coastal rest spot at the Best Western York Inn in York, Maine. 

Day 7 – Exploring Nearby Ogunquit 

What better way to commemorate your road trip across New England than to kick-start the day with a tour around the exquisite Ogunquit Museum of American Art. First opened in 1953 by Lost Generation artist Henry Strater, the museum’s carefully curated collections of art are all displayed against a marvelous backdrop of the venue’s sweeping ocean views out over the Atlantic. 

Finally, before you head home, we recommend celebrating your momentous tour of all six states with a stroll along Ogunquit Beach to let the soft sands and the rhythmic sounds of the waves rejuvenate you before you leave. And, while this may mark the end of your awe-inspiring New England road trip, don’t be surprised if you’re already planning a return trip before you even get home.