The best road cycling routes around Cumberland
5.0
(2)
54
riders
7
rides
Last updated: October 16, 2025
1
riders
1. Greenfield loop via Pennsy Trail — Hancock County
48.3km
01:57
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
23
riders
2. Pennsy Trail loop from Rivoli Park
33.6km
01:26
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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9
riders
3. Central Indiana Canal – Pennsy Trail loop from St. Joseph
77.8km
03:18
170m
170m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
3
riders
4. Pennsy Trail – Mass Avenue loop from Meridian Kessler
72.9km
02:51
170m
170m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
6
riders
5. Charlevoix Lake loop from Trilobi Hills
21.5km
00:57
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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