1

Rambling On East Road, Lenox, Massachusetts

Richmond, MA    

0 out of 5 based on 0 ratings

Highlights: Can we say pastoral? Enjoy fast, curvy dirt road descents? Tread: 7.2 miles on dirt road; 3.2 miles on ...

2

Beartown Trails Epic, Lee, Massachusetts

South Lee, MA    

0 out of 5 based on 0 ratings

Highlights: Riding deep in the woods, imagining yourself as Thoreau. Tread: 13 miles of doubletrack; 2.8 miles of p...

3

The Boulders - Better Than Boulder, Dalton, Massachusetts

Dalton, MA    

0 out of 5 based on 0 ratings

Highlights: Cruising easy trails and waving at joggers and hikers, your mind unburdened by concerns of the Big Bad ...

4

Lenox Mountain, Lenox, Massachusetts

Lenox, MA    

3 out of 5 based on 1 ratings

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...

5

Yokun Ridge Loop, Lenox, Massachusetts

Richmond, MA    

0 out of 5 based on 0 ratings

Highlights: Genuine skinny singletrack with tight turns, unpredictable rolling terrain, and plenty of peace and qui...

6

Cruising In Kennedy, Lenox, Massachusetts

Lenox, MA    

4 out of 5 based on 1 ratings

Highlights: Dancing over an obstacle-strewn uphill you doubted you could, breathing in crisp autumn air in a forest...

7

October Mountain State Forest, Lenox, Massachusetts

Becket, MA    

3 out of 5 based on 1 ratings

In the towns of Lenox, Washington, and Becket, 5 miles north of Interstate 90 and 6 miles south of Pittsfield. Watc...

8

High Country Ponds, Pittsfield, Massachusetts

Pittsfield, MA    

0 out of 5 based on 0 ratings

A high-energy ride up single-track trails to some of the highest-elevation ponds in Massachusetts. Pittsfield State...

9

Kennedy Park, Lenox, Massachusetts

Lenox, MA    

0 out of 5 based on 0 ratings

Miles of fun trails through wooded hills, including such destinations as Balance Rock, a picnic site with a view, a...

10

Dean Hill Road Loop, Richmond, Massachusetts

Richmond, MA    

0 out of 5 based on 0 ratings

Highlights: Cruising fast dirt roads around corners and up and down huge hills. A stunning autumn ride. Tread: 7.5 ...

11

Kennedy Park - Aspinwall Loop, Lenox, Massachusetts

Lenox, MA    

0 out of 5 based on 0 ratings

Highlights: Hairpin turns, roller-coaster singletrack, unpredictable terrain. Tread: 3.6 miles of singletrack; 1.2 ...

12

Ashuwillticook Rail Trail

Massachusetts 8, Pittsfield, MA     (413) 442-8928

4 out of 5 based on 6 ratings

Nestled in the Hoosic River Valley between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashu...

13

John Drummond Kennedy Park, Lenox, Massachusetts

Lenox, MA    

0 out of 5 based on 0 ratings

This is a fine family hiking trip to points of historic interest, including the site of the famed Aspinwall Hotel, ...

14

Pittsfield State Forest

Cascade St, Pittsfield, MA     (413) 442-8992

5 out of 5 based on 6 ratings

Just west of Pittsfield and U.S. Highway 7. The amount of climbing and descending will vary depending on the areas ...

15

Taconic Skyline Trail - Route 20 To Berry Pond, Hancock,...

New Lebanon, NY    

0 out of 5 based on 0 ratings

Highlights: Cruising fast flats, speeding up technical hills that occur infrequently enough for you to remain enthu...