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Western Connecticut Planning Region

Cannondale

Western Connecticut Planning Region

Cannondale

The best running trails around Cannondale

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Running around Cannondale 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 Cannondale—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 16, 2025

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1. Saugatuck, Bedford, & Troop Trail loop — Devil's Den Nature Preserve

11.6km

01:26

120m

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

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Moderate

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2. Town Pond – Merwin Meadows Bath House loop from Wilton

19.2km

02:05

120m

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

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Hard

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3. Lovers Lane Open Space – Merwin Meadows Bath House loop from Cannondale

10.5km

01:05

40m

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

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Moderate

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4. Godfrey Pond loop from Easton

8.70km

01:06

120m

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

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Moderate

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5. Weir Farm loop from Lewisboro

6.63km

00:42

60m

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

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Moderate

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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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The best running trails around Cannondale

1. Saugatuck, Bedford, & Troop Trail loop — Devil's Den Nature Preserve

2. Town Pond – Merwin Meadows Bath House loop from Wilton

3. Lovers Lane Open Space – Merwin Meadows Bath House loop from Cannondale

4. Godfrey Pond loop from Easton

5. Weir Farm loop from Lewisboro

Most popular routes around Cannondale

Most popular attractions around Cannondale

Get inspired with the komoot mobile app

Explore more

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