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)

As temperatures cool between mid- to late September and mid-October, the leaves change from shades of green to bright gold and crimson. Mother Nature and the weather determine exactly when that happens each year. More certain is that higher elevations, such as the northern Berkshires, see the seasonal transformation before the lowlands.

If you’re headed for North Adams and MASS MoCA (FreshGrass Music Festival, September 22-24), take a drive on Route 2 through forests of pine, hemlock, and sugar maples. At an elevation of 1,700 feet, the road winds into a breathtaking hairpin turn with panoramic views of the Hoosac Valley, Mt Greylock, and beyond. Stop along the Blue Vista Motor Lodge, which sits at the highest point of the Mohawk Trail offering 100-mile vistas from each of the guest rooms.

Continue west on Route 2 to Williamstown (or travel from the north and south on Route 7). This college town is also home to The Clark, where you’ll find a vast permanent collection of world-class art, special exhibitions (Edvard Munch ‘Trembling Earth’ through October 15), and a network of walking trails with rewarding views.

Heading south on Route 7 from Williamstown, turn left onto the access road to Mt. Greylock in Lanesborough. This will take you to the Visitors Center via Rockefeller Rd. where you’ll find history and nature exhibits, trail maps, and the start of the tree-lined 8-mile auto road to the summit. 

Back on Route 7, drive south to Pittsfield’s downtown cultural district. Hotel on North is centrally located and a comfy home away from home during your Berkshires fall adventure. Enjoy shops, cafes, theater, and the Berkshire Museum all within walking distance.

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

Picturesque Lenox sits just off Route 7. Well-known as the summer home of the Boston Symphony Orchestra and Tanglewood, it is also a popular fall destination for a restful retreat at an historic inn, Kripalu, Miraval Berkshires, or Canyon Ranch. The compact downtown has unique shopping and excellent eateries. Don’t miss the historic house and gardens built by Edith Wharton at The Mount (outdoor Sculpture Now exhibition) or a nature walk through Mass Audubon’s Pleasant Valley Wildlife Sanctuary. 

On Route 7 in Stockbridge, the iconic Red Lion Inn sits at one of the best people-watching corners in the Berkshires. For lovers of culture, art, and historic estates, there’s Chesterwood, Naumkeag, and the Norman Rockwell Museum nearby. All sit in picture-perfect settings with walking trails that connect you to the natural beauty of the Berkshires. For an enjoyable day hike, there are well-mapped routes in the area maintained by the Berkshire Natural Resources Council, including Jackson Pond, Olivia’s Overlook (Yokum Ridge South), and Stevens Glen.

Follow Route 7 further south to Great Barrington for a hike on Monument Mountain or a stroll through its vibrant downtown, where you’ll find one-of-a-kind shops, award-winning restaurants for every palette, and the Mahaiwe Performing Arts Center. 

Wherever you are in the Berkshires this fall, there are comfortable places to stay with farm-to-table restaurants, microbreweries and wineries nearby. Be sure to also explore the tastes of the Berkshires at local farm stands, orchards, and farmer’s markets!

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

For more world-class travel ideas in the Berkshires, visit berkshires.org. Learn more about visiting Massachusetts at VisitMA.com. 

Return to the Berkshires Blog.