The best cycling routes around Dering Harbor
4.7
(3)
98
riders
10
rides
Looking for the best cycling routes around Dering Harbor? On this page, we bring you the best bike rides around Dering Harbor so you can just get out and go. All you’ve got to do is choose your route!
Last updated: October 21, 2025
5.0
(1)
40
riders
1. Shelter Island Heights – Dickerson Creek loop from Montclair Colony
42.8km
02:37
260m
260m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
4.0
(1)
20
riders
2. Orient Beach State Park – Truman's Beach loop from Southold
47.9km
02:42
120m
120m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
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5.0
(1)
13
riders
3. Shelter Island Heights loop from Hay Beach
23.7km
01:25
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Easy
4
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Easy
4
riders
5. Jockey Creek Bridge loop from Southold
35.8km
02:03
110m
110m
Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular routes around Dering Harbor
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