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!

MASS MoCA, credit Ogden Gigli

Northern Berkshires (Williamstown-North Adams-Pittsfield)

If you’re headed for North Adams and MASS MoCA this fall (FreshGrass Music Festival, September 20-22), take the scenic route. Start with the Mohawk Trail (Route 2), which takes you to a hairpin turn at the North Adams line with breathtaking panoramic views of the Hoosac Valley, Mt. Greylock, and beyond. Stop at the Blue Vista Motor Lodge for eastern-facing views from the highest point on the Trail. If you are visiting on October 6, check out the 68th Annual Fall Foliage Parade! This year’s theme, Berk Du Soleil: The Greatest Show in North Berkshire, promises to be a spectacular show. 

From North Adams, continue to Williamstown and The Clark  for world-class art and mapped woodland hiking trails with views of the surrounding Berkshires.

Continue from Williamstown to Lanesborough and the Mt. Greylock access road. From the Visitor Center parking lot, pick up a trailhead on foot or drive the eight-mile seasonal road to the summit. It can get busy up there during peak foliage season, so plan accordingly.

From Mt. Greylock, head south to Pittsfield’s downtown cultural district to cap off your foliage tour with a stay at Hotel on North. Centrally located in the city and the Berkshires, this small boutique hotel is within walking distance to shops, cafes, theater, and the Berkshire Museum.

Lenoxdale, credit Ogden Gigli

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

Begin your southern Berkshires tour in picturesque Lenox with a stay at an historic inn, Kripalu, Miraval Berkshires, or Canyon Ranch. The walkable downtown area has unique shops and excellent eateries. Plus, there are scenic nature trails at Mass Audubon’s Pleasant Valley Wildlife Sanctuary or Kennedy Park. Don’t miss the historic Gilded Age house and gardens built by Edith Wharton at The Mount (Sculpture at The Mount through October 20).

From Lenox, head to Stockbridge where the iconic Red Lion Inn sits at one of the best people-watching corners in the Berkshires. Chesterwood, Naumkeag, and the Norman Rockwell Museum are all good day trips for art and culture lovers. Each site also has walking trails that connect you to the picture-perfect beauty of autumn in 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 (Yokun Ridge South), and Stevens Glen. If you are seeking a more curated approach, Berkshire Camino and Housatonic Heritage Walks offer myriad guided walks across the Berkshires.

Back on the road, head south to Great Barrington’s downtown cultural district for shopping, a delicious meal, or a performance at the Mahaiwe Performing Arts Center. For a scenic day hike, drive south to Bartholomew’s Cobble or the Appalachian Trail in Sheffield.

Wherever you are in the Berkshires this fall, there are comfortable places to stay with farm-to-table restaurants, microbreweries and wineries close by. 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. Learn more about visiting Massachusetts at VisitMA.com. 

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