The best road cycling routes in Windsor State Forest
41
riders
11
rides
Last updated: October 14, 2025
2
riders
1. Westfield River Access loop from Dalton
48.1km
02:24
720m
720m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
11
riders
2. Plainfield Pond loop from Dalton
83.5km
04:05
1,230m
1,230m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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2
riders
3. View of Lake Ashmere Bridge – East Windsor road loop from Dalton
38.0km
02:00
620m
610m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
4. Pelham Lake Beach – Hoosac Tunnel East Portal loop from Charlemont
81.4km
03:57
1,170m
1,170m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
2
riders
5. Ashuwillticook Rail Trail Head – Trail end loop from Adams
52.9km
02:45
930m
930m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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