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Northwest Hills Planning Region

Chimney Point

Northwest Hills Planning Region

Chimney Point

The best cycling routes around Chimney Point

4.8

(4)

riders

rides

Looking for the best cycling routes around Chimney Point? On this page, we bring you the best bike rides around Chimney Point so you can just get out and go. All you’ve got to do is choose your route!

Last updated: October 27, 2025

4.7

(3)

riders

1. Whalen Pond loop from Brookfield Town Center District

24.9km

01:38

300m

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

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Intermediate

riders

2. Barnum Property loop from Jeanette Heights

14.2km

00:55

180m

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

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Intermediate

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5.0

(1)

riders

3. Leonard Pond – Hatch Pond loop from Sherman

59.8km

03:41

570m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Expert

4. Hearthstone Castle – Lake McDougall loop from Jeanette Heights

37.2km

02:29

510m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Expert

5. Tracy Road Gravel Route – Squantz Pond loop from New Fairfield

50.0km

03:27

800m

Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Expert

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

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The best cycling routes around Chimney Point

1. Whalen Pond loop from Brookfield Town Center District

2. Barnum Property loop from Jeanette Heights

3. Leonard Pond – Hatch Pond loop from Sherman

4. Hearthstone Castle – Lake McDougall loop from Jeanette Heights

5. Tracy Road Gravel Route – Squantz Pond loop from New Fairfield

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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