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.
Last updated: July 7, 2026
4.0
(1)
19
riders
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…
5
riders
112km
04:29
230m
230m
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…

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4.9
(23)
78
riders
30.1km
01:14
70m
70m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.0
(2)
12
riders
143km
06:33
290m
290m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
16
riders
58.5km
02:27
160m
160m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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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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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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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.
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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.
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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 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.
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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.
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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.
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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.


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