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The Berkshires

Area suggestions or local tips? Tell us!

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Distance
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J F M A M J J A S O N D

37 mi 59 km of trail 1 Featured Ride

Easy Trails 3 Trails Intermediate Trails 10 Trails Hard Trails 2 Trails

Local Info

Berkshire County is loaded with hidden singletrack. Head to Balance Rock, Kirvin Park, Pittsfield State Forest, or Kennedy OPark where you can find friendly locals you can ride with or get beta from. The local bike shops like Arcadian Shop, Plaine's, and Berkshire Bike & Board have knowledgeable riders working in the shops who can also provide suggestions or tell you about their weekly rides.

Folks ride year round regardless of weather. Trails will have roots, rocks, downed trees, and other technical elements to navigate. In the fall expect heavy leaf coverage unless the trail fairies have been out blowing. In the winter, expect snow and ice; I recommend studs, bar mitts, and insulated boots. Spring can be wet and muddy. We generally stay off the trails for a day or two after heavy rain to minimize erosion. Enjoy a wonderful shaded canopy all summer long and into the foliage season.

Food & Drink

After the Ride: Local Favorites

SUBWAY februany, non-prem footlongs $5 all Feb long!
924 Hopmeadow St, Simsbury CT — (860) 651-4334
Maple Tree Cafe Fantastic food, great bar and wonderful people! My favorite stop in Simsbury!
781 Hopmeadow St, Simsbury CT — (860) 651-1297
Metro Bis at Simsbury 1820 House Caesar salad was all the white parts of the plant chopped up and no dressing. Trout looked like it was under the heat lamps way too long For THAT price??!!
Joe Pizza Love, Love, Love the pizza! Great place
2 Wilcox St, Simsbury CT — (860) 217-0312
Plan B Burger Bar the burgers are unique in flavor, same for the wide range of beers available
4 Railroad St, Simsbury CT — (860) 658-4477
McLadden's Simsbury Good beer selection, friendly staff and good burgers
6 Wilcox St, Simsbury CT — (860) 408-9626
Peaberry's Cafe May sound strange but the Blueberry Crumble coffee flavor is great. Apple Cinnamon however does NOT work!
712 Hopmeadow St, Simsbury CT — (860) 658-2930
Brookside Bagels Try cinnamon sugar bagel - absolutely amazing
563 Hopmeadow St, Simsbury CT — (860) 651-1492
Little City Pizza The Local Grill is an excellent choice for great innovative food, fabulous staff, and a very laid back and relaxing atmosphere. Walk in with friends, or alone, you will feel very welcomed!
152 Simsbury Rd, Avon CT — (860) 404-5810
Little City Pizza Best pepperoni in the northeast and long trail on tap. Nina is the best!
926 Hopmeadow St, Simsbury CT — (860) 658-4001
Republic Try the truffle popcorn!!
39 Jerome Ave, Bloomfield CT — (860) 216-5852

Featured Rides in The Berkshires - 1

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Trails in The Berkshires - 14

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1.5 mi 2.4 km
#1 Lulu Brook Trail
Lanesborough, MA
1.5 mi 2.4 km Lanesborough, MA
Unknown
Update
0.6 mi 1.0 km
#2 Tappan Zee
Lanesborough, MA
0.6 mi 1.0 km Lanesborough, MA
Unknown
Update
2.0 mi 3.3 km
#3 Turner Trail
Lanesborough, MA
2.0 mi 3.3 km Lanesborough, MA
Unknown
Update
13.3 mi 21.3 km
#4 Taconic Skyline Trail
Lanesborough, MA
13.3 mi 21.3 km Lanesborough, MA
Unknown
Update
2.8 mi 4.5 km
#5 PSF Honolulu Trail
Lanesborough, MA
2.8 mi 4.5 km Lanesborough, MA
Unknown
Update
Lanesborough, MA
1.8 mi 2.9 km Lanesborough, MA
Unknown
Update
1.3 mi 2.1 km
#7 Balance Rock Trail
Lanesborough, MA
1.3 mi 2.1 km Lanesborough, MA
Unknown
Update
3.8 mi 6.0 km
#8 C.C.C. Trail
Richmond, MA
3.8 mi 6.0 km Richmond, MA
Unknown
Update
Lanesborough, MA
1.9 mi 3.0 km Lanesborough, MA
Unknown
Update
Pittsfield, MA
1.3 mi 2.2 km Pittsfield, MA
Unknown
Update
3.0 mi 4.9 km
#11 Burbank Trail
West Stockbridge, MA
3.0 mi 4.9 km West Stockbridge, MA
Unknown
Update
1.6 mi 2.6 km
#12 Daniels Trail
Lanesborough, MA
1.6 mi 2.6 km Lanesborough, MA
Unknown
Update
1.3 mi 2.0 km
#13 Old Baldhead Road
Lenox, MA
1.3 mi 2.0 km Lenox, MA
Unknown
Update
Lenox, MA
0.6 mi 0.9 km Lenox, MA
Unknown
Update

Photos of The Berkshires - 3

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