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Must-See Berkshires Roadside Attractions

Berkshires Roadside Attractions
Camille Reddick
Camille Reddick
June 12, 2026

There's so much beauty hiding in plain sight in the Berkshires! One road trip is all you need to see that this little region tucked into the mountainous countryside of Massachusetts offers peak New England beauty and charm. As you plan your itinerary, it helps to know about some of the best roadside attractions in the Berkshires you might zip past unless you know where to stop. Here's a list of roadside wonders waiting to make your Berkshires trip even more magical.

Herman Melville's Arrowhead

Herman Melville's Arrowhead

Step into a piece of rich literary history with a visit to this stunning farm and estate. Arrowhead is where Herman Melville lived while completing "Moby-Dick" in the early 1850s. Purchased by Melville in 1850, Arrowhead is nestled among the tranquility of nature and the unmatched views of Mount Greylock. In fact, the lure is that Melville actually gained his inspiration for the majestic whale hump in "Moby-Dick" from the sweeping view of the mountain from his property! When you come, you're free to explore this 45-acre estate on your own to capture photos of mountain views, meadow landscapes, and trails. You can also step into the estate to tour Melville's private study and browse the gift shop.

Balance Rock State Park

Part of Pittsfield State Forest, Balance Rock State Park is home to rare geological features that locals simply know as the "strange rocks" in the woods. The naturally occurring rock formation here features a rock precariously balanced on top of a smaller rock, in a gravity-defying display. In addition to snapping a few photos of the rock, you can also enjoy a 3-mile loop trail for hiking, take advantage of one of the many picnicking spots within the park, or follow the more expansive hiking and ATV trails that weave throughout the landscape.

Ashuwillticook Rail Trail

Ashuwillticook Rail Trail

This one's for you if you love walking, jogging, or biking on scenic routes. Ashuwillticook Rail Trail is built over an old railroad line that once ran from Pittsfield to North Adams. Expect views galore as you cover the route! Some notable features include rivers, lakes, ponds, and views of Mount Greylock. The best part is that the trail is flat and paved, making deep immersion in nature feel very accessible. You'll also find plenty of picnic tables where you can stop and rest along the 14 miles of this trail that cut through the beautiful Hoosac River Valley.

Natural Bridge State Park

Don't skip the marble quarry at Natural Bridge State Park in North Adams. Not many people know that this park is home to the only glacier-formed white marble arch in America! Open from mid-May through mid-October, lovely Natural Bridge State Park actually follows the ridgeline of a former quarry. Enjoy an easy walking trail along the cliffs that shows off spectacular views. You can even follow a trail to walk along the top of the gorge within the park. There are also several wonderful picnic spots within the park.

MASS MoCA

MASS MoCA

Not all of the best roadside attractions in the Berkshires are tucked away behind mountains and quarries. The Massachusetts Museum of Contemporary Art (MASS MoCA) is one of the country's premier hubs for contemporary visual art and performing arts. The museum offers 300,000 square feet of open space within its sprawling galleries, more than 75 annual performances and residencies, and dozens of rotating exhibits. You'll definitely want to set aside an entire morning or afternoon to get lost in the splendor and wonder of MASS MoCA's visual and multisensory exhibits.

Finding Unique Beauty in the Berkshires Is Easy

The one thing that's for certain is that you're going to come home with a camera roll full of beautiful and breathtaking photos after stopping at roadside attractions in the Berkshires. In addition to the popular roadside wonders shared here, you can go a little further off the beaten path when you add some of our favorite unique Berkshires roadside attractions to your itinerary.