The best road cycling routes around Cheshire
5.0
(2)
202
riders
7
rides
Last updated: October 29, 2025
38
riders
1. Ashuwillticook Rail Trail Head – Mount Greylock loop from Adams
61.3km
03:07
1,030m
1,030m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
35
riders
2. Rockwell Road – Mount Greylock loop from Lanesborough
63.4km
03:23
1,080m
1,080m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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5.0
(2)
60
riders
3. Roadbike loop from Adams
31.4km
01:26
270m
270m
Intermediate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
4
riders
4. Cheshire Reservoir – Ashuwillticook Rail Trail Head loop from Cheshire
86.0km
04:09
1,180m
1,180m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
5. Cold Spring Preserve – Mount Greylock loop from Lanesborough
101km
05:23
1,910m
1,910m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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