Winchester To Sheepfold
- 11.6 km
- 129 m
- 130 m
- Winchester, Massachusetts, United States
Cycling in Winchester
Discover a map of 70 cycling routes and bike trails near Winchester, created by our community.
Region portrait
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
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
- 8.5 km
- Distance
- 83 m
- Ascent
- 82 m
- Descent
New Winchester to Medford 8/14/25
Cycling route in Winchester, Massachusetts, United States
- 8.2 km
- Distance
- 123 m
- Ascent
- 80 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
- Route in Winchester
- 6.9 km
- 119 m
- 115 m
- Winchester, Massachusetts, United States
- Shore Ride v1
- 82.1 km
- 766 m
- 767 m
- Winchester, Massachusetts, United States
- Downtown to Highlands to Cross St (8mi)
- 13 km
- 63 m
- 60 m
- Winchester, Massachusetts, United States
- 390 S Border Rd, Winchester to 390 S Border Rd, Winchester
- 36.5 km
- 282 m
- 282 m
- Winchester, Massachusetts, United States
- Winchester to Minuteman Bikeway
- 17.7 km
- 79 m
- 62 m
- Winchester, Massachusetts, United States
- Downtown to Highlands to Cross St (5mi)
- 8.2 km
- 50 m
- 49 m
- Winchester, Massachusetts, United States
