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The Berkshires

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287 mi 461 km of trail 2 Featured Runs

Easy Trails 12 Trails Intermediate Trails 15 Trails Hard Trails 4 Trails

Food & Drink

After the Run: 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
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Featured Runs in The Berkshires - 2

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Trails in The Berkshires - 29

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Canaan, CT
89.1 mi 143.4 km Canaan, CT
Unknown
Update
2.4 mi 3.9 km
#2 Mt. Frissell Trail
Canaan, CT
2.4 mi 3.9 km Canaan, CT
Unknown
Update
1.7 mi 2.8 km
#3 Race Brook Trail
Sheffield, MA
1.7 mi 2.8 km Sheffield, MA
Unknown
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Williamstown, MA
1.4 mi 2.3 km Williamstown, MA
Unknown
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1.6 mi 2.6 km
#5 Glen Meadow Loop
Adams, MA
1.6 mi 2.6 km Adams, MA
Unknown
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2.4 mi 3.8 km
#6 Pond Loop Trail
North Adams, MA
2.4 mi 3.8 km North Adams, MA
Unknown
Update
0.5 mi 0.7 km
#7 Shoreline Trail
North Adams, MA
0.5 mi 0.7 km North Adams, MA
Unknown
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13.3 mi 21.4 km
#8 Taconic Skyline Trail
Lanesborough, MA
13.3 mi 21.4 km Lanesborough, MA
Unknown
Update
Lanesborough, MA
1.8 mi 2.9 km Lanesborough, MA
Unknown
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Lanesborough, MA
1.3 mi 2.1 km Lanesborough, MA
Unknown
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3.8 mi 6.0 km
#11 C.C.C. Trail
Richmond, MA
3.8 mi 6.0 km Richmond, MA
Unknown
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Lanesborough, MA
1.9 mi 3.0 km Lanesborough, MA
Unknown
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19.7 mi 31.7 km
#13 South Taconic Trail
Pine Plains, NY
19.7 mi 31.7 km Pine Plains, NY
Unknown
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Sheffield, MA
0.8 mi 1.2 km Sheffield, MA
Unknown
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Bennington, VT
126.2 mi 203.1 km Bennington, VT
Unknown
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Lenox, MA
1.1 mi 1.8 km Lenox, MA
Unknown
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2.6 mi 4.1 km
#17 North Pond Loop
Adams, MA
2.6 mi 4.1 km Adams, MA
Unknown
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1.0 mi 1.6 km
#18 Overbrook Trail
Lenox, MA
1.0 mi 1.6 km Lenox, MA
Unknown
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0.1 mi 0.2 km
#19 Blueberry Trail
North Adams, MA
0.1 mi 0.2 km North Adams, MA
Unknown
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North Adams, MA
0.4 mi 0.6 km North Adams, MA
Unknown
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0.4 mi 0.7 km
#21 Park Trail
North Adams, MA
0.4 mi 0.7 km North Adams, MA
Unknown
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, MA
2.5 mi 3.9 km , MA
Unknown
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3.0 mi 4.8 km
#23 Gould Trail
, MA
3.0 mi 4.8 km , MA
Unknown
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Adams, MA
2.0 mi 3.3 km Adams, MA
Unknown
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Adams, MA
1.8 mi 2.8 km Adams, MA
Unknown
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1.7 mi 2.8 km
#26 Sperry Road
Adams, MA
1.7 mi 2.8 km Adams, MA
Unknown
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, MA
0.4 mi 0.6 km , MA
Unknown
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1.6 mi 2.6 km
#28 Daniels Trail
Lanesborough, MA
1.6 mi 2.6 km Lanesborough, MA
Unknown
Update
North Adams, MA
0.3 mi 0.5 km North Adams, MA
Unknown
Update

Photos of The Berkshires - 10

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