Cycling in Winchester
Discover a map of 61 cycling routes and bike trails near Winchester, created by our community.
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Get to know Winchester
Find the right bike route for you through Winchester, where we've got 61 cycle routes to explore. Most people get on their bikes to ride here in the months of June and August.
1,148 km
Tracked distance
61
Cycle routes
21,374
Population
Community
Most active users in Winchester
From our community
The best bike routes in and around Winchester
Downtown to Highlands to Cross St (8mi)
Cycling route in Winchester, Massachusetts, United States of America
Mostly paved and safe; some intersections.
- 13 km
- Distance
- 63 m
- Ascent
- 60 m
- Descent
Winchester/Arlington/Lexington/Concord/Carlisle Loop
Cycling route in Winchester, Massachusetts, United States of America
- 67.3 km
- Distance
- 395 m
- Ascent
- 354 m
- Descent
Downtown to Highlands 5.3mi
Cycling route in Winchester, Massachusetts, United States of America
Not well paved; sections with no sidewalk; dangerous; DO NOT USE.
- 8.5 km
- Distance
- 83 m
- Ascent
- 82 m
- Descent
Commute to Alnylam
Cycling route in Winchester, Massachusetts, United States of America
- 15.1 km
- Distance
- 63 m
- Ascent
- 68 m
- Descent
Discover more routes
390 S Border Rd, Winchester to 390 S Border Rd, Winchester- Distance
- 36.5 km
- Ascent
- 282 m
- Descent
- 282 m
- Location
- Winchester, Massachusetts, United States of America
Winchester Cycling- Distance
- 9.9 km
- Ascent
- 209 m
- Descent
- 207 m
- Location
- Winchester, Massachusetts, United States of America
Winchester/Arlington/Lexington/Concord/Carlisle With End Hill Loop- Distance
- 74.7 km
- Ascent
- 512 m
- Descent
- 494 m
- Location
- Winchester, Massachusetts, United States of America
Lincoln Street 30, Winchester to Lincoln Street 26, Winchester- Distance
- 19.1 km
- Ascent
- 83 m
- Descent
- 86 m
- Location
- Winchester, Massachusetts, United States of America
57 Salisbury St, Winchester to 2 Mulberry Cir, Andover- Distance
- 33.1 km
- Ascent
- 256 m
- Descent
- 232 m
- Location
- Winchester, Massachusetts, United States of America
Downtown to Highlands to Cross St (5mi)- Distance
- 8.2 km
- Ascent
- 50 m
- Descent
- 49 m
- Location
- Winchester, Massachusetts, United States of America
13 Oak St, Winchester to 186 Kent St, Brookline- Distance
- 17.7 km
- Ascent
- 164 m
- Descent
- 172 m
- Location
- Winchester, Massachusetts, United States of America
From Winchester to Northampton- Distance
- 187.6 km
- Ascent
- 2,132 m
- Descent
- 2,119 m
- Location
- Winchester, Massachusetts, United States of America