The Berkshires Blog

Prettiest Fall Foliage Villages in Massachusetts

New England Foliage, September, 2020
By Necee Regis

Heading to Massachusetts this autumn? Our list of the prettiest fall foliage villages in Massachusetts offers ten spots you won’t want to miss.

When the air turns crisp, and the deciduous forests trade in their tired green attire for vivid hues of crimson, gold and flaming orange, it’s time for a road trip. Here are 10 favorite fall foliage villages in Massachusetts to visit this season.

10 Prettiest Fall Foliage Villages in Massachusetts

New Marlborough

The rural farmlands and surrounding hills make this bucolic town, consisting of five tiny villages, a terrific get-away-from-it-all destination in the lower Berkshires. Make a stop at Umpachene Falls Park, a tributary of the Housatonic, and hike an easy trail to the 40-foot waterfalls.

Mount Greylock State Reservation

At 3,491 feet, the summit is the highest point in Massachusetts and a must-see foliage destination with eye-popping views of the Berkshires and beyond. The reservation offers 70 miles of designated trails for hiking and mountain biking, including an 11.5-mile section of the Appalachian National Scenic Trail.

West Stockbridge

Tucked into the Southern Berkshires, four miles from its better-known neighbor, the area’s ponds, streams, open fields and hills offer lovely spots to enjoy autumn’s colorful displays. The picturesque Williams River flows through the artsy and walkable town center. Don’t miss a stop at Six Depot for breakfast or lunch.

Richmond

Combine leaf-peeping with apple picking and wine tasting in this scenic, rural town abutting the New York State border in the Berkshires. Traverse tree-lined roads alongside open fields that lead to apple farms such as Hilltop Orchards, a popular spot offering sweeping views of rolling hills ablaze with fall color. richmondma.org, hilltoporchards.com

Williamstown

Nestled in the northwesternmost corner of the state, bordering Vermont to the north and New York to the west, this vibrant town—home to Williams College and the Clark Institute—offers terrific foliage-festooned glimpses of the Taconic Range, Brodie Mountain, the Green Mountain National Forest and Mount Greylock.