The best road cycling routes around Wellesley
5.0
(4)
377
riders
46
rides
Last updated: November 4, 2025
22
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
14
riders
2. Farrar Pond from Wellesley Farms
45.0km
01:53
330m
330m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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10
riders
3. Wellesley Hills to Borderland State Park loop via Seekonk Street
84.7km
03:31
600m
600m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4. Wellesley Hills to Lakeville loop via Claybrook Road
196km
08:08
1,050m
1,050m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
78
riders
5. Gregg Conservation Land – Wilsondale Street loop from Wellesley Hills
45.5km
01:57
320m
320m
Intermediate road ride. Good fitness required. 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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