The best running trails around South Windham

10runs

22 people ran here

Running around South Windham 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 South Windham—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.

Cherry Hills Trail loop — Westbrook	Easy 00:30 4.19km
Sebago Lake Land Reserve loop via Half Moon Trail	Intermediate 00:35 5.02km
Poplar Ridge – Lowell Preserve loop from North Falmouth	Expert 02:24 19.0km
Running loop from Westbrook	Easy 00:30 4.90km

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Map data © OpenStreetMap contributors
1
1
Cherry Hills Trail loop — Westbrook
00:30
4.19km
7:15/km
20m
20m
Easy
9
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
2
2
Sebago Lake Land Reserve loop via Half Moon Trail
00:35
5.02km
6:54/km
40m
40m
Intermediate
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Map data © OpenStreetMap contributors
3
3
Poplar Ridge – Lowell Preserve loop from North Falmouth
02:24
19.0km
7:33/km
290m
290m
Expert
6
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
4
4
Running loop from Westbrook
00:30
4.90km
6:12/km
20m
20m
Easy
4
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.