1

Mt. Greylock - Old Adams Road Loop, New Ashford, Massachusetts

Lanesboro, MA    

3 out of 5 based on 1 ratings

Highlights: Fast cruising on Old Adams Road. Raspberries galore in midsummer. Finding a good climbing rhythm up Che...

2

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 ...

3

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...

4

Wahconah Falls

OFF PROSPECT ST, Dalton, MA     (413) 442-8992
Parks 

4 out of 5 based on 2 ratings

Just off Massachusetts Highway 9/8A, between Dalton and Windsor, 8 miles east of Pittsfield. The ride begins with a...

5

Berlin Mountain

Berlin, NY    

0 out of 5 based on 0 ratings

NY and MA are separated by a long mountainous ridge - the Taconic ridge. The Taconic Crest Trail runs along mos...

6

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 ...

7

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...

8

Windsor - Jammin' The Jambs, Windsor, Massachusetts

Plainfield, MA    

0 out of 5 based on 0 ratings

Highlights: Seeing only emerald as you ride through a spruce forest dripping with moss. Tread: 3.7 miles on doublet...

9

Rolling Through The Hilltowns, Worthington, Massachusetts

Worthington, MA    

0 out of 5 based on 0 ratings

Highlights: Lounging at a swimming hole positioned midway through this rural ride. Tread: 14.9 miles on dirt road; ...

10

Savoy Mountain State Forest

260 Central Shaft Rd, North Adams, MA     (413) 663-8469

4 out of 5 based on 8 ratings

This loop follows a two-track multi-use trail through northern hardwood forests, then climbs past Lewis Hill to the...

11

Mount Greylock State Reservation, North Adams, Massachusetts

Williamstown, MA     (413) 499-4262

4 out of 5 based on 2 ratings

Stand atop the Commonwealth?s highest peak, 3,491-foot Mount Greylock, and take in the panoramic five...

12

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 ...

13

The Jambs Of Windsor, Windsor, Massachusetts

Windsor, MA    

0 out of 5 based on 0 ratings

A ride to Windsor Jambs and a tour of the plateau forest. This ride takes you over packed-dirt forest roads and aba...

14

Windsor State Forest*

River Rd, Windsor, MA     (877) 422-6762

0 out of 5 based on 0 ratings

Town of Windsor, 3 miles north of Massachusetts Highway 9, and about 8 miles south of MA 8A. Be prepared to switch ...

15

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...