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Routes
Road cycling routes
United States
Illinois
Cook County

Crestwood

The best road cycling routes around Crestwood

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Road cycling routes around Crestwood, Illinois, are characterized by a network of paved trails and greenways. The area features segments of the Cal-Sag Trail and the Centennial Trail, which traverse diverse landscapes including forest preserves. These routes offer varied terrain with gentle elevation changes, providing options for different fitness levels. The region's infrastructure supports both recreational and more challenging road cycling experiences.

Best road cycling routes around Crestwood

  • The most popular road cycling route is Cal-Sag Trail and Centennial Trail, a 59.8 miles (96.3 km) trail that takes 4 hours 15 minutes to complete. This route connects several communities and offers access to scenic forest preserves.
  • Another top favourite among local road cyclists is Old Plank Road, Cal-Sag & Centennial Trail Loop, a moderate 69.3 miles (111.5 km) path. This loop features a mix of paved surfaces and winds through varied landscapes.
  • Local road cyclists also love the Saganashkee Slough loop from Crestwood, a 25.7 miles (41.4 km) trail leading through natural areas, often completed in about 1 hour 38 minutes.
  • Road cycling around Crestwood is defined by extensive greenway trails, forest preserves, and well-maintained paved surfaces. The network offers options for different ability levels, from easy rides to more challenging routes.
  • The routes in Crestwood are highly rated by the komoot community with an average score of 4.5 stars from over 25 reviews. More than 200 road cyclists have used komoot to explore Crestwood's varied terrain.

Last updated: May 27, 2026

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#1.

Cal-Sag Trail and Centennial Trail

96.3km

04:15

150m

150m

Road cycling the Cal-Sag Trail and Centennial Trail offers a moderate 59.8-mile ride with diverse scenery and connections to other regional

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Moderate

This 69.3-mile (111.5 km) moderate road cycling loop combines the Old Plank Road, Cal-Sag, and Centennial Trails for a diverse ride.

Moderate
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5.0

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

Easy

5.0

(3)

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

Easy

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard
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Popular around Crestwood

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MTB Trails around Crestwood

Tips from the Community

Alex
May 4, 2025, East Shore of Saganashkee Slough

The east shore of Saganashkee Slough in the Palos Forest Preserves offers a popular walking, biking, and fishing spot. Visitors can spot all sorts of birds, including loons, herons, and grebes. The 377-acre lake has trails as well as places to sit and relax.

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Great microbrewery and pizza on the trail in Willow Springs

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mtm05005
July 30, 2024, Lock Number 1

Lock Number 1 is the first lock south of Chicago. It is in the town of Lockport and has a picnic area with views of the canal.

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Amy
February 16, 2024, Centennial Trail

This is a paved 30-mile (48 km) bike trail that traces a former railway line through Snohomish and Skagit county. You ride through beautiful scenery – green farmland, creeks and rivers frame your ride. The trail is shared use so be mindful of pedestrians. Near Arlington, you can connect to the Whitehorse Trail to extend your ride.

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Discover gardens, a waterfall, lakeside trails & native trees in the beautiful nature center and botanic gardens. The lake and gardens are free to enter and provide a beautiful location for a family-friendly stroll.

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The easiest way to explore Greenwood Woods Park is to walk/ride part or all of Thorn Creek Red Paved: a journey into the metropolitan woods!

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Amy
October 18, 2022, Old Plank Road Trail

This is a 22-mile (35 km) paved trail through Sheboygan County. You ride past lots of wildlife en route. Keep your eyes peeled for bald eagles and beavers along the river.

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Amy
October 18, 2022, Hickory Creek Forest

This beautiful preserve protects forests, prairie, savanna and wetland habitats. You'll find lots of wildlife here such as woodpeckers. In winter, trails are open for cross-country and skiing. There are also plenty of picnic shelters – great if you get caught out in the rain on your bike trip.

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Frequently Asked Questions

What kind of road cycling routes can I expect in Crestwood, Illinois?

Crestwood, Illinois, offers a network of paved trails and greenways, primarily featuring segments of the Cal-Sag Trail and the Centennial Trail. These routes traverse diverse landscapes, including scenic forest preserves, and provide varied terrain with gentle elevation changes suitable for different fitness levels.

Are there any easy road cycling routes for beginners or families in Crestwood?

Yes, Crestwood offers several easy routes. For instance, the Cal-Sag Channel – Cal-Sag Trail loop from Crestwood is an easy 8.4-mile (13.6 km) ride with minimal elevation gain, perfect for a relaxed outing or families.

What are some of the longer road cycling routes available in the Crestwood area?

For longer rides, you can explore routes like the Cal-Sag Trail and Centennial Trail, which spans nearly 60 miles (96.3 km). Another option is the Old Plank Road, Cal-Sag & Centennial Trail Loop, a moderate 69.3-mile (111.5 km) path that combines paved surfaces with varied landscapes.

Are there any challenging road cycling routes for experienced riders?

Yes, for a more challenging experience, consider the Saganashkee Slough – Centennial Trail loop from Midlothian. This difficult route covers approximately 89.5 miles (144 km) and features significant elevation changes, making it suitable for experienced road cyclists.

What do other road cyclists enjoy most about cycling in Crestwood?

The road cycling routes in Crestwood are highly rated by the komoot community, with an average score of 4.5 stars from over 25 reviews. Cyclists often praise the extensive greenway trails, the access to scenic forest preserves, and the well-maintained paved surfaces that cater to various ability levels.

Are there any circular road cycling routes in Crestwood?

Yes, many routes in Crestwood are designed as loops. A popular moderate loop is the Saganashkee Slough loop from Crestwood, which is about 25.7 miles (41.4 km) long and leads through natural areas.

What natural attractions can I see along the road cycling routes in Crestwood?

While cycling in Crestwood, you can enjoy natural areas and forest preserves. Notable attractions include Turtlehead Lake, McClaughry Springs Woods, Forty Acre Woods, Palos Preserves, and Tinley Creek Forest Preserve, all of which offer scenic views and natural beauty.

How many road cycling routes are available around Crestwood?

There are over 10 road cycling routes available around Crestwood, offering a variety of distances and difficulty levels for different preferences.

What is the best time of year to go road cycling in Crestwood, Illinois?

The best time for road cycling in Crestwood, Illinois, is generally during the spring, summer, and fall months. These seasons offer pleasant temperatures and favorable conditions for exploring the paved trails and greenways. Always check local weather forecasts before heading out.

Are the road cycling trails in Crestwood well-maintained?

Yes, the road cycling trails in Crestwood, including segments of the Cal-Sag Trail and the Centennial Trail, are known for their well-maintained paved surfaces, providing a smooth and enjoyable riding experience.

Can I find quiet road cycling routes away from heavy traffic in Crestwood?

Many of Crestwood's road cycling routes utilize dedicated paved trails and greenways that wind through forest preserves and natural areas, offering a quieter experience away from vehicular traffic. These routes are ideal for those seeking a peaceful ride.

Most popular routes around Crestwood

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