The best road cycling routes around East Middlebury
5.0
(3)
479
riders
33
rides
Last updated: November 15, 2025
10
riders
1. Chimney Point loop — Middlebury
54.5km
02:22
490m
490m
Moderate 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
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Sign up for free
171
riders
3. Appalachian Gap – Middlebury Gap loop from Middlebury
117km
05:39
1,660m
1,660m
Hard 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
Moderate 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
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular routes around East Middlebury
Most popular attractions around East Middlebury
Get inspired with the komoot mobile app
Explore more
Browse the best Road cycling routes in other regions.
Get ready to conquer new peaks
Sign up for Free