Fall Drives in the Berkshires

Autumn is a beautiful time of year for a road trip. 

Looking for colorful foliage and scenic views? These routes through the Berkshires offer both—plus great places to eat, stay, and explore!

Northern Berkshires (Williamstown-North Adams-Pittsfield)

If you’re headed for North Adams and MASS MoCA (FreshGrass Music Festival, September 19-21), take the scenic route. Start on the Mohawk Trail (Route 2), with its dramatic hairpin turn at the North Adams line and breathtaking panoramic views. If you’re in the area on October 5, check out the city’s beloved Annual Fall Foliage Parade. This year’s cosmic theme, To Northern Berkshire & Beyond, promises to be an extraordinary show!

From North Adams, set out for Williamstown and The Clark  for world-class art and woodland walking trails. Don’t miss the outdoor sculpture exhibition, Ground/work 2025, on campus through October 2026. 

No Berkshire foliage tour would be complete without a visit to Mt. Greylock, the state’s highest peak. Head for the summit via Rockwell Road in Lanesborough or from Notch Road, which begins near Williamstown and North Adams. Both are seasonal routes open until late October, weather permitting.

From Mt. Greylock, cap off your northern Berkshire foliage tour with a stay at Hotel on North in Pittsfield’s downtown cultural district. Centrally located in the Berkshire’s largest city, this boutique hotel is close to shops, cafes, theater, and the Berkshire Museum. Grab a microbrew at Hot Plate Brewing Co., dinner at District Kitchen & Bar, or cocktails at Methuselah Bar and Lounge. Hot Harry’s is a local favorite for tacos and takeout.

Photo by Bill Madden.

Central to Southern Berkshires (Lenox-Stockbridge-Great Barrington)

Begin your southern Berkshires tour in picturesque Lenox with a stay at an historic inn or wellness resort. The town’s annual Apple Squeeze festival is a highlight of the autumn season (September 27). Nearby, walking trails at Mass Audubon’s Pleasant Valley Wildlife Sanctuary, Kennedy Park, and Parsons Marsh Reserve showcase the changing colors of the autumn landscape. Into haunted happenings? Get in the spirit of the season with a ghost tour at The Mount or Ventfort Hall (minimum age 12).

From Lenox, head south to Stockbridge. Spend a cozy night at The Inn at Stockbridge or the iconic Red Lion Inn. Art and culture lovers will enjoy a visit to Chesterwood, Naumkeag, and the Norman Rockwell Museum. For an enjoyable day hike, take one of the well-mapped routes maintained by the Berkshire Natural Resources Council, or join a curated guided experience with Housatonic Heritage Walks.

Back on the road, head south to Great Barrington’s downtown cultural district for shops, restaurants, or a performance at the Mahaiwe Performing Arts Center. Drive to Bartholomew’s Cobble or the Appalachian Trail in Sheffield for a scenic day hike. For picnic goodies, stop at Guido’s Fresh Marketplace or the Berkshire Food Co-Op (and don’t forget the sweet treats at Robin’s Candy Shop)!

Wherever you are in the Berkshires this fall, there are comfortable places to stay near farm-to-table restaurants, microbreweries and wineries. Local orchards and farmer’s markets offer seasonal produce. And did we mention the fresh cider donuts at farm stands along the way?

Find more of what’s happening in the Berkshires this fall here.

For more world-class travel ideas in the Berkshires, visit berkshires.org.  

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