The best road cycling routes around Winthrop
4.5
(220)
7,417
riders
147
rides
Last updated: September 20, 2025
5.0
(4)
27
riders
1. Boston to Deer Island Park via Deer Island Loop Trail
25.1km
01:03
80m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
2
riders
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
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4.8
(4)
72
riders
3. Nahant Road views – Devereux Beach loop from Revere Beach
54.5km
02:23
210m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
26
riders
4. Donovan's Beach – Revere Beach loop from Orient Heights
28.3km
01:12
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
16
riders
5. Bremen Street Park – Winthrop Beach loop from Airport
24.9km
01:02
110m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
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