Want to go road cycling around Winnetka? We’ve reviewed all of the road rides around Winnetka to identify the best. Explore them all here, and find your perfect road cycling …

Last updated: September 22, 2025

5.0

(17)

102

riders

1. Skokie Lagoons – Skokie Lagoon No. 3 loop from Hubbard Woods

24.0km

00:57

40m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

3.5

(2)

218

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2. Lakefront Trail, Chicago – Lincoln Park loop from Kenilworth

52.4km

02:07

100m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Intermediate

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5.0

(1)

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3. Harms Woods Preserves – Caldwell Woods loop from Indian Hill

45.9km

01:58

70m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

5.0

(7)

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4. Shelton Park – Founders Park loop from Winnetka

34.8km

01:32

140m

Intermediate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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Intermediate

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5. Founders Park – Christ Church Churchyard loop from Hubbard Woods

32.0km

01:24

80m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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The best road cycling routes around Winnetka

1. Skokie Lagoons – Skokie Lagoon No. 3 loop from Hubbard Woods

2. Lakefront Trail, Chicago – Lincoln Park loop from Kenilworth

3. Harms Woods Preserves – Caldwell Woods loop from Indian Hill

4. Shelton Park – Founders Park loop from Winnetka

5. Founders Park – Christ Church Churchyard loop from Hubbard Woods

Most popular routes around Winnetka

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