The best cycling routes around Lenox
5.0
(1)
55
riders
23
rides
Last updated: October 27, 2025
17
riders
1. Housatonic River Reservoir – Card Pond loop from West Stockbridge
42.9km
02:46
510m
510m
Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
4
riders
2. Gould Meadows loop from Stockbridge
27.2km
01:50
320m
320m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3
riders
3. George Canon Road loop from Lee
43.1km
02:46
530m
530m
Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
4. Olivia's Overlook loop from Lenox
28.4km
01:53
430m
430m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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