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Rambling On East Road, Lenox, Massachusetts
Highlights: Can we say pastoral? Enjoy fast, curvy dirt road descents? Tread: 7.2 miles on dirt road; 3.2 miles on ...
Beartown Trails Epic, Lee, Massachusetts
Highlights: Riding deep in the woods, imagining yourself as Thoreau. Tread: 13 miles of doubletrack; 2.8 miles of p...
The Boulders - Better Than Boulder, Dalton, Massachusetts
Highlights: Cruising easy trails and waving at joggers and hikers, your mind unburdened by concerns of the Big Bad ...
Lenox Mountain, Lenox, Massachusetts
Not the longest trip but lots of fun, with a nice track that?s a warm-up for a very challenging climb to a great mo...
Yokun Ridge Loop, Lenox, Massachusetts
Highlights: Genuine skinny singletrack with tight turns, unpredictable rolling terrain, and plenty of peace and qui...
Cruising In Kennedy, Lenox, Massachusetts
Highlights: Dancing over an obstacle-strewn uphill you doubted you could, breathing in crisp autumn air in a forest...
October Mountain State Forest, Lenox, Massachusetts
In the towns of Lenox, Washington, and Becket, 5 miles north of Interstate 90 and 6 miles south of Pittsfield. Watc...
High Country Ponds, Pittsfield, Massachusetts
A high-energy ride up single-track trails to some of the highest-elevation ponds in Massachusetts. Pittsfield State...
Kennedy Park, Lenox, Massachusetts
Miles of fun trails through wooded hills, including such destinations as Balance Rock, a picnic site with a view, a...
Dean Hill Road Loop, Richmond, Massachusetts
Highlights: Cruising fast dirt roads around corners and up and down huge hills. A stunning autumn ride. Tread: 7.5 ...
Kennedy Park - Aspinwall Loop, Lenox, Massachusetts
Highlights: Hairpin turns, roller-coaster singletrack, unpredictable terrain. Tread: 3.6 miles of singletrack; 1.2 ...
Ashuwillticook Rail Trail
Nestled in the Hoosic River Valley between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashu...
John Drummond Kennedy Park, Lenox, Massachusetts
This is a fine family hiking trip to points of historic interest, including the site of the famed Aspinwall Hotel, ...
Pittsfield State Forest
Just west of Pittsfield and U.S. Highway 7. The amount of climbing and descending will vary depending on the areas ...
Taconic Skyline Trail - Route 20 To Berry Pond, Hancock,...
Highlights: Cruising fast flats, speeding up technical hills that occur infrequently enough for you to remain enthu...