The best running trails around Wainscott
117
runners
36
runs
Running around Wainscott is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes around Wainscott—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.
Last updated: November 5, 2025
3
runners
1. Spring Tree and Old Railroad loop — Sag Harbor
8.05km
00:57
20m
20m
Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.
Intermediate
2
runners
2. Northwest Path to Scoy Pond loop — Grace Estate
18.4km
02:15
130m
130m
Expert run. Very good fitness required. Mostly accessible paths. Some sure footedness required.
Expert
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9
runners
3. Short Bay loop from Redwood
11.7km
01:12
30m
30m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
7
runners
4. Lily Pond loop from East Hampton
5.22km
00:32
10m
10m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Intermediate
8
runners
5. Running loop from East Hampton
16.1km
01:41
50m
50m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Expert
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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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