Prettiest Fall Foliage Villages in Massachusetts

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

Ashburnham

Hikers and foliage lovers flock to this small, historic town to ascend Mount Watatic (elevation: 1,832 feet), an undeveloped mountain east of the Connecticut River in northern Worcester County. On a clear fall day, the rocky double summit offers views of a carpet of colors in every direction, including Mount Wachusett to the south, and Mount Monadnock to the north. ashburnham-ma.gov/Pages/index

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. newmarlboroughma.gov/pages/index

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. mass.gov/eea/agencies/dcr/massparks/region-west/mt-greylock-state-reservation-generic.html SEE MORE: The New American Hogwarts is So New England and We Love It

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. weststockbridgetown.com

Shelburne Falls

This historic village in Franklin County offers quintessential New England fall foliage photo ops along the Bridge of Flowers, a 400-foot-long trolley bridge spanning the Deerfield River. In addition to more than 500 varieties of flowers that bloom through October, the bridge offers vistas of the colorful surrounding hills. shelburnefalls.com SEE MORE: The Bridge of Flowers | From Ragweed to Roses

Boylston

Incorporated in 1786, this small village with a historic town common borders the Wachusett Reservoir, a recreational areas with hiking and walking trails offering wonderful foliage views. It is also home to the scenic, 132-acre Tower Hill Botanical Garden, open year round. mass.gov/eea/agencies/dcr/massparks/region-central/wachusett-reservoir.html, towerhillbg.org

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. williamstownchamber.com

North Andover

For scenic foliage hikes not far from Boston, this Essex County town—bordered by the Merrimack River and Lake Cochichewick—is home to Weir Hill, a Trustees of Reservations preserve with hiking paths offering sweeping views of the Merrimack Valley and beyond. thetrustees.org/places-to-visit/north-shore/weir-hill.html

Petersham

Adjacent to the conservation lands of the Quabbin Reservoir—the largest inland body of water in the state—this picturesque town in Worcester Country is also home to the Federated Women’s State Forest, Swift River Reservation and the Harvard Forest, all offering trails and hikes with great leaf-peeping opportunities. harvardforest.fas.harvard.edu SEE MORE: Lost Towns of the Quabbin Reservoir What tops your list of favorite foliage villages in Massachusetts? This post was first published in 2016 and has been updated. 

SEE MORE: Prettiest Fall Foliage Villages in Vermont Prettiest Fall Foliage Villages in Southern New England New England Weekend Fall Foliage Planner 10 Places to Visit in New England in Fall 

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