The best road cycling routes around Dedham
4.6
(92)
3,066
riders
302
rides
Last updated: October 26, 2025
9
riders
1. Massachusetts to Rhode Island Loop
105km
04:28
740m
740m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
2. Lake Massapoag loop – road cycling in MA
49.7km
02:05
400m
400m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Sign up for free
3
riders
3. Crystal Lake & Jamaica Pond loop from Dedham
26.9km
01:08
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4. Wachusett Mountain Climb from Needham via Carville Basin
160km
07:20
1,720m
1,720m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
29
riders
5. Claybrook Road – Wilsondale Street loop from Islington
42.8km
01:49
340m
340m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular attractions around Dedham
Get inspired with the komoot mobile app
Explore more
Browse the best Road cycling routes in other regions.
Get ready to conquer new peaks
Sign up for Free