The Upper Berkshires is packed with mountain views, hidden waterfalls, fascinating history, and unforgettable outdoor adventures, making it one of the best road trip destinations in Massachusetts.
Along the way, you’ll discover incredible places that are easy to miss if you only stick to the main highways, with everything from impressive natural wonders to fascinating historic sites and picture perfect small towns.
Whether you want to hike to breathtaking viewpoints, learn something new, or simply take a relaxing drive through the mountains, this route has something waiting around every corner.
Fill up the gas tank, grab your camera, and get ready for an Upper Berkshires road trip that is full of memorable stops, amazing scenery, and plenty of reasons to take your time.
1. Hancock Shaker Village
Hancock Shaker Village is located in Pittsfield, just off Route 20 in the beautiful Berkshires.
This living history museum preserves one of the best-surviving Shaker communities in the United States, with 20 historic buildings set within a walkable village on a 750-acre property.
Step inside the famous Round Stone Barn, built in 1826 with a unique circular design that made feeding livestock more efficient.
Then tour the Brick Dwelling, workshops, and gardens while learning how the Shakers became known for simple furniture, seed sales, and inventive craftsmanship.
Costumed interpreters, hands on demonstrations, heritage breed sheep, goats, chickens, and walking trails make it easy to picture everyday Shaker life during the 1800s.
2. Ashuwillticook Rail Trail
After exploring centuries of history, head to the Ashuwillticook Rail Trail, a paved 12.7-mile path stretching from Adams through Cheshire to Lanesborough, where you can walk, bike, or rollerblade past some of the Berkshires’ prettiest scenery.
The trail follows a former railroad line along the shoreline of Cheshire Reservoir, giving you long water views, mountain backdrops, peaceful forests, and plenty of benches and picnic spots for a relaxing break.
Keep your eyes open for great blue herons, ducks, bald eagles, and other wildlife, especially during the quieter morning hours, and bring a camera because the views of Mount Greylock are fantastic on clear days.
With mostly gentle grades, convenient parking areas, bike rental options nearby, and easy access to local restaurants and ice cream shops in Adams and Cheshire, this is one of the best outdoor stops on an Upper Berkshires road trip.
3. Mount Greylock State Reservation
Make your way to Mount Greylock State Reservation, home to Massachusetts’ highest peak at 3,491 feet, where scenic roads, hiking trails, and sweeping mountain views steal the show.
Drive the 16.3-mile Mount Greylock Scenic Byway or tackle popular hikes like the 6.6-mile round-trip Cheshire Harbor Trail.
Then climb the Veterans War Memorial Tower for incredible views stretching across Massachusetts, New York, Vermont, New Hampshire, and Connecticut on clear days.
More than 70 miles of trails wind through the reservation, including a section of the famous Appalachian Trail, passing waterfalls, hardwood forests, and rocky overlooks that change beautifully with every season.
Pack a picnic, stop by the Bascom Lodge near the summit for a meal or overnight stay, and visit in autumn when brilliant red, orange, and golden leaves turn this mountain into one of the most spectacular fall color destinations in New England.
4. Adams
Next, spend some time in Adams, a small Berkshire town packed with local history, outdoor adventures, and easy access to several top attractions.
Start at the Susan B. Anthony Birthplace Museum to learn about the famous women’s rights leader, then stroll through the compact downtown filled with historic brick buildings, local cafés, and independently owned shops.
Adams also hosts community events throughout the year, including the annual Fall Foliage Festival, making it a fun stop where you can mix history, great scenery, and small town charm in one easy visit.
5. Natural Bridge State Park
Just a few minutes from downtown Adams, Natural Bridge State Park protects North America’s only natural white marble arch.
Carved by glacial meltwater flowing through Hudson Brook around 13,000 years ago, it remains one of the area’s most striking geological landmarks.
An easy network of walking paths takes you past the natural marble bridge spanning a steep 60-foot gorge and the remains of an old marble quarry.
Signs along the way explain how the region’s famous marble formed and how it was later quarried for buildings throughout the Berkshires.
You can also watch the rushing water tumble through the narrow rock channel, spot unique marble formations, and enjoy shady picnic areas surrounded by towering cliffs and forest.
6. The Cascades Trail (North Adams)
If you’re ready to stretch your legs again, head to The Cascades Trail in North Adams, where a short, family friendly hike leads to one of the Berkshires’ most beautiful waterfalls.
The well marked out-and-back trail is about 2.1 miles round trip, winding through a shady forest before reaching The Cascades, a waterfall that drops about 45 feet over moss-covered rocks into a cool, clear pool.
Wooden footbridges, small streams, and the sound of rushing water make the walk just as enjoyable as the destination, especially after a rainy day when the falls are at their strongest.
Wear sturdy shoes because sections of the trail can be rocky and muddy, and bring a camera to capture one of the most photographed waterfalls in the northern Berkshires.
7. Williamstown
Slow the pace in Williamstown, a charming college town in the northwest corner of Massachusetts that blends world class art, scenic streets, and beautiful mountain views.
Spend a few hours exploring the renowned Clark Art Institute, home to works by Renoir, Monet, and Winslow Homer.
Then wander the museum’s 140-acre campus, where walking trails, meadows, reflecting pools, and water basins are framed by the Taconic and Berkshire Mountains.
Just a short drive away, the Williams College Museum of Art showcases an impressive collection spanning thousands of years.
Nearby Spring Street is lined with local bookstores, cafés, restaurants, and specialty shops that are perfect for an afternoon stroll.
If you are visiting in summer, check the schedule for the Williamstown Theatre Festival, a nationally recognized performing arts event that has welcomed celebrated actors, directors, and playwrights for decades.
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