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Southold

Southold

The best cycling routes around Southold

4.6

(8)

145

riders

16

rides

Looking for the best cycling routes around Southold? On this page, we bring you the best bike rides around Southold so you can just get out and go. All you’ve …

Last updated: September 22, 2025

5.0

(1)

38

riders

1. Shelter Island Heights – Dickerson Creek loop from Montclair Colony

42.8km

02:37

260m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

4.0

(1)

19

riders

2. Arshamomaque Cemetery – Mitchell Park loop from Southold

58.5km

03:22

130m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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5.0

(1)

12

riders

3. Shelter Island Heights loop from Hay Beach

23.7km

01:25

130m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

9

riders

4. Beach – Jockey Creek Bridge loop from Laughing Waters

17.3km

01:00

50m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

4

riders

5. Hashamomuck Beach – Horton Point Lighthouse loop from Greenport West

19.4km

01:08

60m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

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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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