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and the Appalachian Trail, which enters Massachusetts here, provide miles of hiking trails and other recreational opportunities and preserve a natural landscape that feels wild and remote, yet is close to Routes 23, 44 and 22, and the Taconic Parkway.

New Marlborough

New Marlborough, which traces its history to 1738, encompasses New Marlborough village and the hamlets of Clayton, Hartsville, Mill River, and Southfield. Bordering North Canaan, Connecticut, it is 15-20-minute drive from Great Barrington. A sophisticated rural, residential community, New Marlborough retains its historic character in its charming village green, around which cluster the original New England Meeting House, now a venue for concerts, lectures, and art shows, Gedney Farm, and The Old Inn on the Green, a charming 18th-century stagecoach inn still in operation: the Inn’s restaurant is considered one of the best in the region. Other eateries are The Southfield Store, Gedney Farm, and Cantina 229. A portion of Lake Buel borders New Marlborough. Other recreational amenities include Cookson State Forest, access to the Sandisfield State Forest, Umpachene Falls, and the Konkapot River.


Otis is a small rural community along the southeastern border of Berkshire County, bordering Becket, Tyringham, Monterey, and Sandisfield. Encompassing several second-home, lake-access communities, it is crossed by Routes 8 (north-south) and 23 (eastwest). The town enjoys a diverse landscape with soaring elevations, a beautiful reservoir, open fields, and marsh. Outdoor recreation is year-round, with fishing, water sports, skiing, and hiking in a variety of settings, including the Otis Reservoir, the largest recreational body of water in Massachusetts, Tolland State Forest, Otis Ridge Ski Resort, and fishing in various lakes, ponds, and the Farmington River. First settled because of the location along the Old Knox Trail, it was incorporated in 1810 as the town of Otis, honoring politician Harrison Gray Otis, whose Boston home now headquarters Historic New England, the preservation organization.


This bucolic New England town, nestled between the Farmington River Valley and Sandy Brook, is the largest by area in Berkshire County. Home to only about 800 full-time residents, its population swells to 2,500 in summer, thanks to its country ambiance, beautiful landscapes, serenity, and outdoor recreational amenities. These include Sandisfield State Forest and York Lake, the Farmington and Clam rivers, Upper Spectacle Pond, West Lake, and Yanner Park. First settled in 1750 and incorporated in 1762, Sandisfield retains a thriving logging industry, numerous farms, nurseries, an apple orchard, and the New Boston Inn, an 18th-century stagecoach stop that is still in operation. Bordering Connecticut, Sandisfield is about 25 minutes southeast of Great Barrington.