The best road cycling routes around North Chicago
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Road cycling around North Chicago offers diverse routes through varied natural landscapes. The region features extensive forest preserves, such as Fort Sheridan Forest Preserve, providing serene settings for rides. Cyclists can explore river trails like the Des Plaines River Trail, which meanders through woodlands and prairies. The area also benefits from its proximity to the Lake Michigan shoreline, offering scenic views and well-maintained paths.
Best road cycling routes around North Chicago
- The most popular road cycling route is Fort Sheridan…
Last updated: July 12, 2026
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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riders
43.1km
01:57
160m
160m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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22
riders
31.8km
01:22
90m
90m
The Skokie Valley Bikeway offers a smooth, flat asphalt path, ideal for road cycling and maintaining a steady pace. While you'll encounter some stretches paralleling US 41 and train tracks,…
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The Fort Sheridan Forest Preserve road cycling loop from Green Oaks offers a delightful and accessible ride, showcasing stunning Lake Michigan views from 70-foot bluffs. As you pedal, you'll traverse…
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38
riders
35.4km
01:33
120m
120m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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Tips from the Community
Fort Sheridan Forest Preserve, an Illinois gem, combines history and nature. Amidst remnants of the former military base, discover scenic trails, woodlands, and Lake Michigan's shoreline for a diverse outdoor experience.
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This bronze sculpture is a tribute to General Sheridan, a Civil War general. It depicts him on a horse during Battle of Five Forks in April 1865.
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This forest preserve offers a quiet escape from the city with a good selection of trails. All the trails are well marked and well maintained. You can also connect to the Des Plains River Trail to explore further afield.
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You get a lovely view of the Fort Sheridan Pond and the woodland surrounding it. With such a lovely view directly from the relatively quiet road, this is a lovely spot to pass by on your cycle.
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Explore the picturesque Green Bay Trail, a delightful 9-mile route paralleling Chicago's Metra commuter rail line north of the city. Winding through North Shore towns like Kenilworth, Winnetka, Highland Park, and Lake Bluff, the trail is adorned with charming homes, community parks, and convenient amenities. Given its proximity to Lake Michigan, you can opt for shorter on-road side trips to savor beachfront views.
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Trees, ponds and flowers make the Old School Forest Preserve an ideal habitat for many animal species, flowers and more. Here you can completely immerse yourself in nature.
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The statue captures Sheridan astride his mount "Rienzi," inspiring his troops during the pivotal Battle of Five Forks in April 1865, a symbol of his leadership and victory. Visit Fort Sheridan to admire this iconic sculpture, commemorating a key figure in American history.
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Northcroft Park is a 30-acre beautifully maintained park that offers a large pavilion, playground equipment, tennis courts, soccer fields, and restrooms.
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Frequently Asked Questions
How many road cycling routes are available in North Chicago?
There are over 19 road cycling routes around North Chicago, offering diverse options for various skill levels. These routes are highly rated by the komoot community, with an average score of 5.0 stars.
What types of landscapes can I expect to see while road cycling in North Chicago?
Road cycling in North Chicago offers a variety of landscapes, including extensive forest preserves like Fort Sheridan, serene river trails such as the Des Plaines River Trail, and scenic views along the Lake Michigan shoreline. You'll encounter woodlands, prairies, wetlands, and savannas.
Are there road cycling routes suitable for beginners or less experienced cyclists?
Yes, North Chicago offers many easy road cycling routes. For example, the Fort Sheridan Cemetery loop from Great Lakes is an easy 14-mile (22.5 km) ride, and the Rockland Wetlands – Old School Forest Preserve loop from Lake Bluff is another easy 19.7-mile (31.7 km) option that traverses diverse ecosystems.
What natural attractions can I explore along the road cycling routes?
Many routes pass by beautiful natural attractions. You can cycle near Independence Grove Lake, explore the MacArthur Woods Forest Preserve, or discover the Pond in Sedge Meadow Forest Preserve. The Des Plaines River Trail itself meanders through diverse ecosystems like tallgrass savanna and oak woodlands.
Are there any longer road cycling routes for more endurance-focused riders?
For longer rides, consider routes like the Des Plaines River Trail – Old School Forest Preserve loop from Libertyville, which spans over 25 miles (40.5 km) and offers extensive views of forest preserves and riverine landscapes.
What do other road cyclists enjoy most about the routes in North Chicago?
The routes in North Chicago are highly rated by the komoot community, with an average score of 5.0 stars from over 5 reviews. Cyclists often praise the well-maintained paths, the serene natural settings of the forest preserves, and the diverse ecosystems encountered along river trails.
Can I find circular road cycling routes in the North Chicago area?
Yes, many of the road cycling routes in North Chicago are designed as loops, allowing you to start and end at the same point. Examples include the Fort Sheridan Forest Preserve – Fort Sheridan Forest Preserve loop from Green Oaks and the Northcroft Park – Skokie Valley Bikeway loop from Lake Forest.
Are there any specific trails that are particularly scenic for road cycling?
The Des Plaines River Trail is considered a 'crown jewel' for its scenic beauty, winding through diverse ecosystems. The Fort Sheridan Forest Preserve also offers beautiful loops with views of the natural surroundings. Additionally, segments of the North Shore Trails provide excellent paths away from busy streets.
What is the best time of year for road cycling in North Chicago?
The spring, summer, and fall months generally offer the best conditions for road cycling in North Chicago, with pleasant temperatures and vibrant natural scenery. Fall, in particular, can be beautiful with changing foliage in the forest preserves.
Are there any urban or cultural points of interest accessible by bike near North Chicago?
While many routes focus on natural areas, the broader North Shore area features bike paths that connect to local restaurants and shops. The Chicago Botanic Garden in nearby Glencoe is also a renowned living museum with extensive landscapes that can be explored, and it's accessible by bike.
Are the road cycling routes in North Chicago generally family-friendly?
Many of the easy and moderate routes, especially those within forest preserves and dedicated bike paths like segments of the Des Plaines River Trail, are suitable for families. These trails often provide a safe and enjoyable environment away from traffic.
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