Cycling in Winchester
Discover a map of 70 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 70 cycle routes to explore. Most people get on their bikes to ride here in the months of July and August.
1,304 km
Tracked distance
70
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
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
- 67.3 km
- Distance
- 395 m
- Ascent
- 354 m
- Descent
Downtown to Highlands 5.3mi
Cycling route in Winchester, Massachusetts, United States
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
- 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
Winchester Cycling- Distance
- 9.9 km
- Ascent
- 209 m
- Descent
- 207 m
- Location
- Winchester, Massachusetts, United States
Winchester/Arlington/Lexington/Concord/Carlisle With End Hill Loop- Distance
- 74.7 km
- Ascent
- 512 m
- Descent
- 494 m
- Location
- Winchester, Massachusetts, United States
Lincoln Street 30, Winchester to Lincoln Street 26, Winchester- Distance
- 19.1 km
- Ascent
- 83 m
- Descent
- 86 m
- Location
- Winchester, Massachusetts, United States
57 Salisbury St, Winchester to 2 Mulberry Cir, Andover- Distance
- 33.1 km
- Ascent
- 256 m
- Descent
- 232 m
- Location
- Winchester, Massachusetts, United States
Downtown to Highlands to Cross St (5mi)- Distance
- 8.2 km
- Ascent
- 50 m
- Descent
- 49 m
- Location
- Winchester, Massachusetts, United States
13 Oak St, Winchester to 186 Kent St, Brookline- Distance
- 17.7 km
- Ascent
- 164 m
- Descent
- 172 m
- Location
- Winchester, Massachusetts, United States
New Winchester to Medford 8/14/25- Distance
- 8.2 km
- Ascent
- 123 m
- Descent
- 80 m
- Location
- Winchester, Massachusetts, United States