The best cycling routes around Winchester
4.4
(335)
5,676
riders
267
rides
Last updated: October 13, 2025
18
riders
1. Middlesex Fells Bicycle Loop
9.94km
00:57
110m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
7
riders
2. Mystic River loop — Arlington
40.7km
02:24
120m
120m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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2
riders
3. Horn Pond loop — Boston, Massachusetts
10.6km
00:44
100m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(10)
58
riders
4. Battle Road Trail – Minuteman Bikeway loop from Arlington Heights
37.4km
02:33
160m
160m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.8
(6)
28
riders
5. Minuteman Bikeway – Lexington Battle Green loop from West Medford
51.3km
03:01
230m
230m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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