Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Road cycling routes
United States
Illinois
Cook County

Crestwood

The best road cycling routes around Crestwood

4.7

(55)

378

riders

15

rides

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

Last updated: July 7, 2026

4.0

(1)

19

riders

#1.

Cal-Sag Trail and Centennial Trail

96.3km

04:15

150m

150m

The Cal-Sag Trail and Centennial Trail offers a diverse road cycling experience, blending natural beauty with glimpses of the urban landscape. You'll pedal past the serene Saganashkee Slough, enjoy shaded…

Navigate with device

Send to Phone

Save

Moderate

The Old Plank Road, Cal-Sag & Centennial Trail Loop offers a diverse road cycling experience, combining three distinct paved paths into one substantial journey. You'll glide along the flat, smooth…

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

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

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
Sign up for free to see 11 more rides around Crestwood.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

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

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Crestwood

Hiking around Crestwood

Running Trails around Crestwood

Cycling around Crestwood

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.

1

0

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.

0

0

RJC
May 18, 2024, Saganashkee Slough

Some of these routes take you on roads that are absolutely not safe for cycling. Do your own research about the routes ahead of time.

0

0

Lisa
February 26, 2024, Cal-Sag Trail

This multi-use trail runs along the Cal-Sag Channel, which was built to reverse the flow of the Little Calumet River and direct sewage away from Lake Michigan.

0

0

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.

1

0

oliviakellis
January 26, 2024, Cal-Sag Channel

Discover the Cal-Sag Channel, a 16-mile-long watercourse in southern Cook County, created between 1911 and 1922. Initially designed for drainage, it ingeniously reversed the flow of the Little Calumet River, redirecting sewage away from Lake Michigan. This dual-purpose canal now supports shipping activities and offers a distinctive environment for water enthusiasts and history buffs alike.

0

0

Javi Jaavii
January 25, 2024, Turtlehead Lake

Turtlehead Lake is a highly popular spot for fishing lovers in the area, where you can stop to rest and enjoy its picnic areas and the beauty of nature.

1

0

Bethan Owens
December 21, 2023, Turtlehead Lake

Turtlehead Lake is a lovely lake surrounded by well-kept grassland. There is a multi-use trail around the eastern perimeter of the lake, which is paved and relatively flat. There are various picnic tables, some of which are within shelters and can be reserved ahead of time. This is a popular place for people to go fishing.

1

0

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

Easy hikes around Crestwood

Most popular attractions around Crestwood

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Road cycling routes in other regions.

ChicagoBurnhamDoltonWilmetteEvanstonRiverdaleCalumet CityPullman National MonumentBellwoodBlue IslandRobbinsStone ParkSchiller ParkHarveyBurbankBridgeviewNilesBedford ParkMerrionette ParkWillow SpringsSouth HollandJusticeSauk VillageNorthlakeAlsipFranklin ParkHodgkinsIndian Head ParkCountrysideMelrose ParkElmwood ParkGolfEvergreen ParkRosemontHometownGlencoeGlenwoodChicago RidgeOak LawnWorthDes PlainesDeer Grove Nature PreserveRiver GroveLynwoodMarkhamMidlothianPark RidgeWinnetkaHickory HillsPalos HillsCountry Club HillsRolling MeadowsBerkeleyBarrington HillsNorridgeHarwood HeightsOak ForestForest ParkFord HeightsCiceroBerwynWheelingNorthbrookHillsideRiver ForestDixmoorPosenMorton GroveSkokieBroadviewBusse WoodsPhoenixHomewoodBarringtonLincolnwoodStreamwoodCalumet ParkPalos HeightsWestchesterHeritage Quarries Recreation AreaSouth BarringtonChicago HeightsOak ParkNorthfieldSchaumburgCrabtree PreserveLansingEast Hazel CrestPalatineInvernessHoffman EstatesLemontLa Grange ParkMaywoodSpring Lake PreservePalos ParkKenilworthMount ProspectElk Grove VillageThorntonProspect HeightsLa GrangeMccookRiversideForest ViewGlenviewHazel CrestArlington HeightsOrland ParkWestern SpringsSpring Lake Forest PreserveStegerTinley ParkLyonsBrookfieldNorth RiversideSummitMattesonStickneyOrland HillsRichton ParkFlossmoorOlympia FieldsSouth Chicago HeightsPark Forest

Nearby adventure guides

Things to Do around Midlothian

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy