4.6
(101)
504
riders
50
rides
Touring cycling routes around Highland Park feature a landscape characterized by a network of paved bikeways, forest preserves, and river corridors. The region offers varied terrain, including trails alongside the Skokie River and routes connecting to Lake Michigan. Dedicated bicycle lanes and shared roadways are part of the local infrastructure, enhancing accessibility for cyclists. These routes often traverse green lawns, native gardens, and restored woodlands, providing a scenic backdrop for rides.
Last updated: May 29, 2026
5.0
(9)
21
riders
43.2km
02:31
130m
130m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.8
(10)
16
riders
42.1km
02:34
90m
90m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
12
riders
45.4km
02:48
160m
160m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(22)
47
riders
42.8km
02:29
60m
60m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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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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If you are biking along the North Branch Red Paved Trail or the dirt horse trail that follows the Skokie River, you'll pass through a bunch of different parks and preserves. The Watersmeet Woods is one of those natural preserves that the trails pass through.
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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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Erickson Woods welcomes visitors with convenient amenities, such as picnic shelters and parking, providing access to the well-frequented trail system at Skokie Lagoons. The extensive network of over seven miles of paved trails meanders through Skokie Lagoons, featuring a 4.4-mile loop encompassing a significant portion of the lagoons and a 1.5-mile paved link to the North Branch Trail System.
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Situated where the east and middle forks of the Chicago River merge, Watersmeet Woods earns its name from this distinctive convergence. The varied collection of trees, shrubs, sedges, grasses, and wildflowers within this natural haven thrives thanks to the continuous efforts of volunteers participating in the North Branch Restoration Project.
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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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Hiking, running, and biking are popular activities in this area, with the well-known North Branch Trail running through and providing both paved and unpaved trails to enjoy. The North Branch of the Chicago River also flows through the area, offering scenic water views.
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This trail system provides a choice between paved and unpaved trails, offering over 20 miles winding through various preserves and along the North Branch Chicago River.
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There are over 45 touring cycling routes around Highland Park, offering a diverse range of options for cyclists. These routes are highly rated by the komoot community, with an average score of 4.8 stars.
The touring cycling routes in Highland Park primarily feature a network of paved bikeways, often traversing forest preserves and river corridors. You'll find varied terrain, including trails alongside the Skokie River and routes connecting to Lake Michigan, with many routes offering mostly paved surfaces through green lawns, native gardens, and restored woodlands.
Yes, Highland Park offers many easy routes suitable for families and beginners. For instance, the North Branch Black Paved Trail β North Branch Trail loop from Hubbard Woods is an easy 16.9-mile (27.2 km) route featuring mostly paved surfaces through natural preserves. Overall, 29 of the 46 available routes are classified as easy.
Many routes offer scenic views and pass by notable natural features. You can explore areas like the Skokie Lagoons, the Skokie River, and various forest preserves. Specific highlights include Skokie Lagoon No. 3, MacArthur Woods Forest Preserve, and the North Branch Trail itself, which is a significant cycleway.
Yes, many touring cycling routes in Highland Park are designed as loops, allowing you to start and end at the same point. Examples include the Grosse Point Lighthouse β Green Bay Trail loop from Lake Forest and the Small Lake β Skokie Valley Bikeway loop from Fort Sheridan.
Highland Park offers pleasant cycling conditions through spring, summer, and fall. The region's forest preserves and native gardens are particularly vibrant during these seasons. While some trails might be accessible in winter, the primary cycling season benefits from milder weather and fully accessible paved paths.
While specific regulations vary by preserve and trail section, many forest preserves in the Highland Park area are dog-friendly, often requiring dogs to be on a leash. It's advisable to check local signage or the specific preserve's website for the most current rules regarding pets on trails you plan to visit.
Highland Park and surrounding areas, including forest preserves, generally offer designated parking areas near trailheads. The city's 'MoveHP Plan' aims to improve access, including for cyclists, suggesting that parking facilities are considered for trail users. Specific parking availability may vary by route starting point.
For those seeking longer rides, the Grosse Point Lighthouse β Green Bay Trail loop from Lake Forest covers 41.1 miles (66.2 km) and is rated moderate. Another moderate option is the Skokie Lagoons β North Branch Trail loop from Fort Sheridan, which is 33.3 miles (53.6 km).
The area is highly rated by the komoot community, with an average score of 4.8 stars from over 80 reviews. Reviewers often praise the well-maintained paved surfaces, the scenic beauty of the forest preserves and river corridors, and the accessibility of routes that connect various natural areas and local destinations.
Yes, some routes utilize the Green Bay Trail, which offers views towards Lake Michigan. For example, the Grosse Point Lighthouse β Green Bay Trail loop from Lake Forest provides opportunities to experience the lake's proximity and views.
The duration varies significantly by route and your cycling pace. Easy routes like the North Branch Black Paved Trail β North Branch Trail loop from Hubbard Woods can take around 1 hour 33 minutes. Longer, moderate routes such as the Skokie Lagoons β North Branch Trail loop from Fort Sheridan might take approximately 3 hours 21 minutes.


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