Cycling in Chesterfield
Discover a map of 26 cycling routes and bike trails near Chesterfield, created by our community.
Region portrait
Get to know Chesterfield
Find the right bike route for you through Chesterfield, where we've got 26 cycle routes to explore.
1,261 km
Tracked distance
26
Cycle routes
1,222
Population
Community
Most active users in Chesterfield
From our community
The best bike routes in and around Chesterfield
Windsor loop
Cycling route in Chesterfield, Massachusetts, United States of America
From West Chesterfield past the Cummington Fair.Route 9 ino Windsor and up fist slope of Windsor Mountain Left onto cut over to 143, en 143 back to West Chesterfiel
- 33.2 km
- Distance
- 444 m
- Ascent
- 442 m
- Descent
Chesterfield-Holyoke (South St)
Cycling route in Chesterfield, Massachusetts, United States of America
One unpaved section in Easthampton climbing the back way to get to Southampton Rd in Holyoke. TOURING BIKE ONLY
- 38.6 km
- Distance
- 382 m
- Ascent
- 738 m
- Descent
Therese's weeknight ride
Cycling route in Chesterfield, Massachusetts, United States of America
Start at the Chesterfield Gorge. Leaving the parking lot, turn right onto Ireland Street. Follow Ireland Street to the intersection of route 143. At the stop sign, go straight across the intersection and onto Cummington Road. Follow Cummington Road into Cummington (it becomes Fairgrounds Road)
- 13 km
- Distance
- 177 m
- Ascent
- 177 m
- Descent
Ashfield Loop w/Chesterfield Gorge
Cycling route in Chesterfield, Massachusetts, United States of America
- 52.1 km
- Distance
- 849 m
- Ascent
- 852 m
- Descent
Discover more routes
Ashfield Loop- Distance
- 38.9 km
- Ascent
- 533 m
- Descent
- 536 m
- Location
- Chesterfield, Massachusetts, United States of America
Goshen - Holyoke- Distance
- 38.1 km
- Ascent
- 108 m
- Descent
- 497 m
- Location
- Chesterfield, Massachusetts, United States of America
Therese's Trek- Distance
- 55.1 km
- Ascent
- 554 m
- Descent
- 554 m
- Location
- Chesterfield, Massachusetts, United States of America
Therese's Work Ride- Distance
- 10.7 km
- Ascent
- 264 m
- Descent
- 264 m
- Location
- Chesterfield, Massachusetts, United States of America
Chesterfield-Holyoke (East St)- Distance
- 39.7 km
- Ascent
- 313 m
- Descent
- 670 m
- Location
- Chesterfield, Massachusetts, United States of America
Worthington Loop- Distance
- 44.6 km
- Ascent
- 842 m
- Descent
- 842 m
- Location
- Chesterfield, Massachusetts, United States of America
Hyde Hill Loop- Distance
- 20.9 km
- Ascent
- 391 m
- Descent
- 395 m
- Location
- Chesterfield, Massachusetts, United States of America
Shelburne Falls Road Route- Distance
- 69.6 km
- Ascent
- 952 m
- Descent
- 956 m
- Location
- Chesterfield, Massachusetts, United States of America