Massachusetts Road Trip Itinerary Nobody Tells
There are hidden gems, historic small towns and scenic routes that many travelers miss in Massachusetts.
Although Boston and Cape Cod get a lot of attention, there’s so much else to see in this stunning New England state.
If you are seeking the road trip of a lifetime that goes off the beaten path, this itinerary will take you through some of Massachusetts’ best-kept secrets.
1. First Stop: Shelburne Falls — The Quaint Functional Town of Bridges and Flowers
Start in the scenic town of Shelburne Falls, in the foothills of the Berkshires.
Just northwest of Amherst is the lesser-known town of Shelburne Falls, famous for the Bridge of Flowers, an old trolley bridge transformed into a private walkway/flower garden.
If you’re there for a few days, this is a beautiful pedestrian walkway, which is covered with colorful blooms from spring to fall, and the best spot to walk in the morning.
A few steps down the road from the bridge, you can stroll along the Glacial Potholes in the Deerfield River.
The glacier creates these natural formations where the water began to swirl, a geological wonder worth seeing.
2. Mohawk Trail: Historic Scenic Drive
Out of Shelburne Falls, hop in your car and travel along the iconic Mohawk Trail.
Once a Native American trade route, this scenic byway boasts some of the state’s most breathtaking views.
Take a pit stop at the highest peak in Massachusetts, Mount Greylock.
The drive to the summit gives you panoramic views for as far as 90 miles if the weather is clear.
Be sure to visit the Veterans War Memorial Tower at the summit.
Another interesting stop along the route is the Western Gateway Heritage State Park in North Adams.
This gives you some background on the legendary Hoosac Tunnel, a 19th-century marvel of engineering.
3. Head to the Creative Hub of North Adams, Massachusetts
Continue your travels to North Adams, a small city with a big art scene.
MASS MoCA, among the largest contemporary art centers in the country, is in North Adams.
This sprawling museum, which occupies a repurposed factory complex, can easily take a few hours to explore.
With a constantly rotating selection of exhibitions, installations and performances, the museum is not to be missed for art lovers.
A drive short drive from downtown, Natural Bridge State Park is home to the only natural white marble arch in North America.
The short hike to see the bridge (and surrounding gorge) is just as impressive, providing a unique natural playground.
4. Take Me to the Berkshires: Nature, Culture and Small-Town Charm
The Berkshires area is a cultural and natural wonderland.
From rolling hills to colorful art scenes, there’s something for everyone.
Start in Lenox, a lovely town full of cultural attractions, including Tanglewood, the summer residence of the Boston Symphony Orchestra.
If you’re visiting in the summer, don’t miss seeing a concert here.
If you’re in Lenox, visit The Mount, the historic home of the author Edith Wharton.
The mansion and its exquisitely manicured gardens provide a menagerie of the Gilded Age.
Traveling south: Great Barrington, a vibrant town with a fantastic food scene and quirky shops.
You can hike Monument Mountain nearby, for more spectacular views of the Berkshires.
These articles help you make the most of your trip.
5. On the return trip east, you could detour to the tiny village of Shelburne in Franklin County
Backend here, past Shelburne Farm and Deli, a local farm stand serving fresh produce, homemade pies and other local goodies.
The farm is particularly famous for its apple cider donuts, a fall classic.
Nearby in South Deerfield, Magic Wings Butterfly Conservatory houses more than 4,000 butterflies.
It’s a magical experience, especially for families, and gives you a serene stop on your road trip.
6. Concord: Where History Meets Nature
As you head further toward Boston, spend a day in Concord, a town where America’s history and literary significance collide.
Stroll the battlefields at Minute Man National Historical Park, where the first shots of the American Revolution were fired.
Its scenic trails along the path of the original battle make it both a historic and picturesque destination.
See the mecca of Walden Pond, where Henry David Thoreau lived and wrote the poetry of Walden.
You can swim, hike the surrounding trails, or just soak in the tranquility at Walden Pond.
7. Coastal Ipswich: beaches with colonial history
No road trip in Massachusetts would be complete without some coastal fare. Go to Ipswich for the beautiful beaches and the history.
Begin with what’s arguably the most gorgeous beach in New England, Crane Beach.
It’s well-suited for a quiet walk along the sand dunes or a cool plunge in the Atlantic.
After the beach, one option is to tour Castle Hill on the Crane Estate, a palatial 59-room mansion built on 3,500 acres of manicured grounds.
The Great House is open for tours and the grounds reveal sweeping views of the ocean.
Cap off the day with a stroll through Russell Orchards, a family-owned farm where you can pick-your-own apples, sample fresh-made cider, and enjoy tasty baked goods.
8. Salem: Witch Trials and Oceanside Charm
Finish your road trip in Salem, a town known for its 1692 witch trials and maritime history.
Explore the dark past of the Salem Witch Trials at the Salem Witch Museum, which features an engaging and educational experience about this notorious chapter in American history.
Visit the House of the Seven Gables, the historic home that inspired Nathaniel Hawthorne’s classic novel.
The house and gardens are sumptuously preserved, affording a glimpse of life in the 17th century.
Take a stroll along the waterfront at Pickering Wharf, where you can shop, feast at waterfront restaurants and even enjoy a sunset cruise to finish your trip on a high note.
Massachusetts Road Trip Itinerary Conclusion
Massachusetts has its quirks, and this road trip itinerary hits some of the state’s most unusual and off-the-radar tourism spots.
From the art-centric streets of North Adams to the storied beauty of Concord to the coastal haven of Ipswich, this trip is a trifecta of art, history and nature.
Pack your bags, buckle up and explore the Massachusetts you don’t hear about in the news.
