The best road cycling routes around Great Barrington
219
riders
36
rides
Last updated: October 27, 2025
39
riders
1. Hudson and Leet Ore Beds Ponds – Gould Meadows loop from Great Barrington
60.9km
02:44
630m
630m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
15
riders
2. Roadbike loop from Egremont Plain
41.4km
02:01
370m
370m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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12
riders
3. Gould Meadows – Barbieri Reservoir loop from Great Barrington
50.2km
02:13
470m
470m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
4. Piano Pond loop from Egremont Plain
51.2km
02:33
490m
490m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
5. Elisabeth Freeman Denkmal statue loop from Great Barrington
61.8km
02:57
480m
480m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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