The best cycling routes around Winchester
5.0
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16
riders
5
rides
Last updated: November 1, 2025
2
riders
1. Fort Hill Recreational Trail — Hindsdale, New Hampshire
21.3km
02:00
110m
110m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
2. Winchester to Swanzey loop via Ashuelot Rail Trail — Cheshire County
45.0km
03:24
220m
220m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3
riders
3. Keene to Wincester via Ashuelot Rail Trail
42.0km
03:47
130m
130m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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3
riders
4. Ashuelot Rail Trail loop from Keene
52.8km
03:26
450m
450m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
5. Ashuelot Rail Trail – Troy Train Depot loop from Fitzwilliam
69.1km
04:32
640m
640m
Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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