4.7
(45)
355
riders
14
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.
Last updated: May 27, 2026
4.0
(1)
19
riders
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
4
riders
112km
04:29
230m
230m
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.

Sign up for free
5.0
(17)
61
riders
41.3km
01:52
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(3)
56
riders
31.1km
01:11
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(2)
14
riders
144km
06:32
290m
290m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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
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
Great microbrewery and pizza on the trail in Willow Springs
1
0
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
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
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.
0
0
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!
0
0
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.
1
0
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.
1
1
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.
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.
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.
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.
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.
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.
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.
There are over 10 road cycling routes available around Crestwood, offering a variety of distances and difficulty levels for different preferences.
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.
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.
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.


Browse the best Road cycling routes in other regions.