10 Of The Quietest Massachusetts Towns
Peel away Massachusetts's college towns and Revolutionary War landmarks and what remains is a quieter half of the state. Hill towns of a few hundred people. Cape Cod fishing villages. A Wampanoag-owned commercial district on Martha's Vineyard. Berkshire estates whose owners summered alongside Edith Wharton and J.P. Morgan's sister. Some of the ten towns below sit next to a 1957 drive-in still showing first-run films through the summer. Some are anchored by 4,000-acre state forests with no commercial development for miles. Some have populations under 200. The ten communities below are slower than the parts of the state most travelers see, in some cases markedly so.
Stockbridge
Stockbridge sits in the southern Berkshires with several specific anchors packed into a small footprint. The Norman Rockwell Museum, the largest collection of Rockwell's original work in the country, holds 998 paintings and drawings on a 36-acre estate that includes Rockwell's relocated studio. The Berkshire Botanical Garden, in continuous operation since 1934, runs 24 acres of cultivated and native gardens open from May 1 through October 30. Naumkeag House and Gardens, a 44-room shingle-style house designed by Stanford White in 1885 for Joseph Choate (later US Ambassador to the United Kingdom), sits on 8 acres of landscaped grounds with an ice-blue Blue Steps stairway designed by landscape architect Fletcher Steele. From late June through Labor Day, Tanglewood, the summer home of the Boston Symphony Orchestra since 1937, runs a music festival across an open lawn just over the town line in Lenox.
Rockport
Rockport sits at the eastern tip of Cape Ann, a working harbor town that has held an artists' colony since the late 19th century. The painted red fishing shack on Bradley Wharf, known as Motif No. 1, is one of the most painted buildings in the country and has been reconstructed at least twice on the original ground. The Thacher Island Twin Lights, two granite lighthouses on a 50-acre island half a mile offshore, are the only operating twin-light pair on the East Coast and can be reached by ferry through the warm months. Millbrook Meadow, a four-acre downtown park, holds a frog pond, a stone bridge, and resident wildlife including ducks, beavers, and otters. Several of the working galleries on Bearskin Neck and Main Street trace their lineage back to the 1920s Rockport Art Association.
Lenox
Lenox hosts Tanglewood across the town line each summer and runs the Berkshires' densest concentration of Gilded Age estates. The Mount, Edith Wharton's home from 1902 to 1911, is preserved as a National Historic Landmark with its 1902 gardens restored and the house open for self-guided tours, evening lectures, and an outdoor sculpture program. Ventfort Hall, the 1893 Jacobean Revival summer house of Sarah Spencer Morgan (sister of J.P. Morgan), is open for tours and runs a working museum on Gilded Age life in the Berkshires. Mass Audubon's Pleasant Valley Wildlife Sanctuary, a 1,300-acre preserve, runs seven miles of trails through wetlands, beaver ponds, and hardwood forest with a marked summit climb to Lenox Mountain.
Wellfleet
Wellfleet, on the lower Cape, has been an oyster town since the 17th century and runs roughly 100,000 bushels of cultivated oysters from its harbor each year. The Wellfleet Bay Wildlife Sanctuary, a 1,100-acre Mass Audubon property at the southern edge of town, runs five miles of trails across pine woods, salt marsh, and a tidal flat, with naturalist-led programs through the warm months. The Wellfleet Drive-In, opened in 1957 on Route 6, is one of the last operating drive-ins in New England and still runs first-run double features through the summer. The Wellfleet Farmers Market on Main Street follows a clear seasonal rhythm: asparagus and strawberries in spring, corn and tomatoes in summer, cranberries and squash in autumn.
Raynham
Raynham, in southeastern Massachusetts, was first settled by English colonists in 1652 as part of the original Bridgewater purchase from Wampanoag sachem Massasoit. The Raynham Flea Market, at the corner of Routes 24 and 44, runs every Sunday year-round with about 500 dealers across 16 acres of indoor and outdoor space, the largest flea market in southeastern New England. Massasoit State Park, a 1,500-acre forest with three ponds and roughly 11 miles of mixed-use trails, runs hiking, mountain biking, fishing, and seasonal camping. The Hannant House, a 1770s Cape-style home that serves as the Raynham Historical Society headquarters, is open to the public by appointment. The Milk Bottle, a Route 44 roadside diner inside an actual oversized milk bottle, runs a long-standing breakfast trade with a house omelet on the menu.
Aquinnah
Aquinnah occupies the western tip of Martha's Vineyard and is the smallest town on the island by population, with around 300 year-round residents. The Aquinnah Cultural Center, in the 1890 Edwin DeVries Vanderhoop Homestead, runs exhibits on the Wampanoag Tribe of Gay Head (Aquinnah), the federally recognized tribe whose ancestral land includes the entire town. The shops at the Aquinnah Circle on the cliffs are tribally owned, with profits returning to the tribe. The Gay Head Cliffs, a National Natural Landmark, drop about 150 feet from the lighthouse to the water in bands of red, yellow, gray, and white clay, and they hold fossil deposits from the Cretaceous and Pleistocene. Lobsterville Beach, a long stretch of low-traffic shoreline on the northern coast of the town, is the standing locals' beach.
Monroe
Monroe, in the far northwestern corner of Massachusetts, has the second-smallest population of any town in the state at around 110 year-round residents. Monroe State Forest covers 4,321 acres and runs from sunrise to sunset year-round with marked hiking, horseback, and snowmobile trails, plus access to Hunt Hill (a 2,420-foot summit with a fire-tower platform that gives a clear view across the Deerfield River valley into Vermont). The Deerfield River, on the southern edge of town, runs Class II to IV whitewater on dam-released water through the Dryway and Fife Brook sections, with several outfitters running guided rafting trips out of nearby Charlemont. The town has no commercial district to speak of; access is via Monroe Road off Route 2.
Warwick
Warwick is a north-central hill town on Route 78 against the New Hampshire border, anchored by Mount Grace State Forest. The forest covers 1,689 acres and includes Mount Grace itself, which rises to 1,617 feet and is one of the higher summits in north-central Massachusetts; a marked western trail reaches the summit fire tower in roughly an hour and a half. Warwick State Forest, also along Route 78, runs additional hiking and includes Sheomet Lake (stocked with brook and brown trout each spring) and the Indian Cave, a small natural rock shelter accessible by a short trail. The Warwick Historical Society holds a regional collection of photographs, costumes, furniture, and tools from the town's 19th-century industrial period.
New Salem
New Salem, in southeastern Franklin County, has just under 1,000 year-round residents and sits on the eastern shore of the Quabbin Reservoir. The Quabbin protects 81,000 acres of watershed land for the Boston metro water supply, all of it closed to motorized access; foot traffic, bicycles, and horses are permitted, with marked trails running from gates around the perimeter. The Swift River Valley Historical Society in town runs a museum on the four towns (Dana, Enfield, Greenwich, and Prescott) that were dismantled and flooded in the 1930s to create the reservoir. The Bear's Den, a small gorge on the Middle Branch of the Swift River, is a quarter-mile walk from a small parking area off Neilson Road and drops about 70 feet through bedrock to a small waterfall and pool. The annual Old Home Day each September runs games, crafts, food, and music on the town common.
Plainfield
Plainfield, in the western Hampshire County hills along Route 116, sits on the Mohawk Trail extension and is one of the smaller hill towns in the Berkshires at around 650 year-round residents. The Westfield River, a federally designated Wild and Scenic River for 78 miles of its main stem and tributaries, runs along the southern edge of town with road-accessible fishing access and shoreline walking. Dubuque Memorial State Forest covers 7,822 acres on the eastern side of town with 35 miles of marked trails for mountain biking, hiking, and snowmobiling, plus canoeing, kayaking, and trout fishing on Hallockville Pond.
Bay State Of Mind
The ten towns above sit at the quieter end of the state's range, from a 110-person hill town in the northwest corner to a Wampanoag enclave on the western tip of Martha's Vineyard. Each runs on something specific (a 1957 drive-in, a Wharton estate, a 4,000-acre state forest, the Quabbin watershed, a federally Wild and Scenic river) and the right one for a weekend mostly comes down to which anchor matches the trip.
