The best road cycling routes around Rutland
5.0
(7)
38
riders
17
rides
Last updated: November 9, 2025
3
riders
1. Wachusett Loop
81.7km
03:55
990m
990m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(3)
5
riders
2. MA Mountain Loop
83.4km
04:13
1,010m
1,010m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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3. Holden to Sterling – road cycling in MA
17.1km
01:03
60m
170m
Easy road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
5.0
(3)
5
riders
4. Quinapoxet Reservoir – Central Tree of Massachusetts loop from Holden
80.3km
04:08
940m
940m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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