Running around Chimney Point 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 Chimney Point—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: October 4, 2025

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1. Zalesskys Pond – Parkhurst Pond loop from New Milford

12.8km

01:22

190m

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

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Intermediate

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2. Whalen Pond loop from Brookfield Town Center District

6.82km

00:43

60m

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

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3. Running loop from New Milford

5.04km

00:32

50m

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

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4. Running loop from Brookfield Town Center District

9.62km

01:00

60m

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

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5. Ball Pond loop from Jeanette Heights

5.64km

00:35

30m

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

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

Most popular routes around Chimney Point

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Cycling around Chimney Point

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Browse the best Running Trails & Routes in other regions.

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The best running trails around Chimney Point

1. Zalesskys Pond – Parkhurst Pond loop from New Milford

2. Whalen Pond loop from Brookfield Town Center District

3. Running loop from New Milford

4. Running loop from Brookfield Town Center District

5. Ball Pond loop from Jeanette Heights

Most popular routes around Chimney Point

Get inspired with the komoot mobile app

Explore more

Get ready to conquer new peaks

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