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Routes
Road cycling routes
United States
Illinois
Cook County
Chicago

Caldwell Woods – Des Plaines River loop from Gladstone Park

Routes
Road cycling routes
United States
Illinois
Cook County
Chicago

Caldwell Woods – Des Plaines River loop from Gladstone Park

Moderate

5.0

(8092)

9,562

riders

Caldwell Woods – Des Plaines River loop from Gladstone Park

02:02

42.2km

70m

Road cycling

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: June 14, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 29.4 km for 291 m

Open: • sunrise-sunset (otherwise closed)

After 32.8 km for 69 m

Open: • sunrise-sunset (otherwise closed)

Waypoints

A

Start point

Train Station

Get Directions

1

3.14 km

Caldwell Woods

Highlight • Forest

Caldwell Woods, situated on Chicago's northwest side, offers diverse recreational features including picnic groves, activity spaces, a warming shelter, sledding hill, and access to the well-loved North Branch Trail. Despite …

Tip by

2

4.28 km

Bunker North Flatwoods

Highlight • Forest

This area is known for its natural expanses, offering an ideal habitat for diverse wildlife. It forms part of the extensive 20-mile North Branch Trail System, which is popular for hiking, running, and biking.

Tip by

3

6.43 km

North Branch Red Paved Trail

Highlight (Segment) • Trail

Stretching for about 20 miles, this trail meanders along the North Branch Chicago River, providing a serene experience surrounded by the sights and sounds of nature. The well-maintained trail offers pleasant shade amidst lush greenery.

Tip by

4

10.8 km

Linne Woods Preserve

Highlight • Forest

Linne Woods Preserve is a nature preserve in Morton Grove, Illinois. A number of trails pass through the property, which is centered around the wetland and forest ecosystems created by …

Tip by

20.1 km

Forest Preserve District of Cook County

Nature Reserve

6

21.4 km

Des Plaines River

Highlight • River

Des Plaines River flows 133 miles (214 km) flows through Wisconsin and Illinois before joining the Kankakee River. It's the longest stream in Chicago.

Tip by

7

31.4 km

Road bike off road

Highlight • Trail

beautiful section of trail

Tip by

8

31.6 km

Robinson Woods North Trail Along Des Plaines River

Highlight • Trail

This area offers a nice unpaved trail that follows along the Des Plaines River, providing enjoyable views and sounds as you ride. The park is named after Alexander Robinson, the English name of Potawatomi chief Chee-chee-pin-quay, born in 1787.

Tip by

9

32.6 km

Robinson Woods South

Highlight • Forest

This area offers a nice unpaved trail that follows along the Des Plaines River, providing enjoyable views and sounds as you ride. The park is named after Alexander Robinson, the English name of Potawatomi chief Chee-chee-pin-quay, born in 1787.

Tip by

B

42.2 km

End point

Train Station

Loading

Way Types & Surfaces

Way Types

19.4 km

13.4 km

5.06 km

4.03 km

191 m

< 100 m

< 100 m

Surfaces

31.6 km

5.60 km

4.44 km

512 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Today

Tuesday 14 July

36°C

23°C

0 %

Additional weather tips

Max wind speed: 11.0 km/h

to get more detailed weather forecasts along your route

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