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Northeastern Connecticut Planning Region

South Windham

Northeastern Connecticut Planning Region

South Windham

The best running trails around South Windham

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runs

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.

Last updated: November 14, 2025

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1. Hanks Hill Pond – Fifty-Foot Cliff Preserve loop from Mansfield Center Historic District

24.3km

02:53

280m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

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2. Mansfield Hollow Lake – Mansfield Hollow State Park loop from Mansfield Center Historic District

15.1km

01:46

110m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

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3. Bibbins Pond – Froenbauch Pond loop from Scotland

21.9km

02:19

240m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

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4. Running loop from Main Street Historic District

10.7km

01:07

80m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

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5. Brousseous Pond – Clarks Hill loop from Lebanon Green Historic District

16.7km

01:45

150m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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The best running trails around South Windham

1. Hanks Hill Pond – Fifty-Foot Cliff Preserve loop from Mansfield Center Historic District

2. Mansfield Hollow Lake – Mansfield Hollow State Park loop from Mansfield Center Historic District

3. Bibbins Pond – Froenbauch Pond loop from Scotland

4. Running loop from Main Street Historic District

5. Brousseous Pond – Clarks Hill loop from Lebanon Green Historic District

Most popular routes around South Windham

Most popular attractions around South Windham

Get inspired with the komoot mobile app

Explore more

Get ready to conquer new peaks

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