The best road cycling routes around Middlebury
5.0
(3)
467
riders
27
rides
Last updated: October 22, 2025
10
riders
1. Chimney Point loop — Middlebury
54.5km
02:22
490m
490m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
2. Forest Dale & Brandon loop — Middlebury
65.6km
02:47
550m
560m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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171
riders
3. Appalachian Gap – Middlebury Gap loop from Middlebury
117km
05:39
1,660m
1,660m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
32
riders
4. Huntington Falls loop from Middlebury
39.3km
01:45
390m
390m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
5. Middlebury Falls – Main Street loop from Middlebury
78.8km
03:21
620m
620m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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