The best road cycling routes in Addison County
5.0
(3)
651
riders
53
rides
Last updated: September 27, 2025
10
riders
1. Chimney Point loop — Middlebury
54.5km
02:22
490m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
4
riders
2. Forest Dale & Brandon loop — Middlebury
65.6km
02:47
550m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
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61
riders
3. Rochester – Brandon Gap loop from Granville
94.6km
04:54
1,170m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
Expert
141
riders
4. Middlebury Gap – Appalachian Gap loop from Middlebury
117km
05:38
1,620m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
Expert
28
riders
5. Huntington Falls loop from Middlebury
39.3km
01:45
390m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
20
riders
6. Middlebury Falls – Main Street loop from Middlebury
78.8km
03:21
620m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
24
riders
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
19
riders
8. Leicester loop from Salisbury
22.3km
00:57
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
17
riders
9. Spade Farm Covered Bridge loop from Ferrisburgh
29.6km
01:11
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
19
riders
10. Main Street – Middlebury Gap loop from Middlebury
49.1km
02:21
680m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
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