The best road cycling routes around Medfield
4.6
(76)
780
riders
134
rides
Last updated: October 22, 2025
5.0
(4)
9
riders
1. Walpole to Dover Loop
49.1km
02:19
460m
460m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2. Medfield to Moose Hill Reservation loop via Willet Pond
44.9km
01:52
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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1
riders
3. Walpole to Sudbury Reservoir loop via Ashland
89.3km
03:49
640m
640m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(4)
7
riders
4. Tangerini Farm – North Street loop from Walpole
44.9km
02:01
410m
410m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
5. Claybrook Road – Gregg Conservation Land loop from Sherborn
28.7km
01:17
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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