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United States
Illinois
Lake County

Highland Park

The best cycling routes around Highland Park

4.6

(101)

504

riders

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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.

Best touring cycling routes around Highland Park

  • The most popular touring cycling route is North Branch Black Paved Trail – North Branch Trail loop from Hubbard Woods, a 16.9 miles (27.2 km) trail that takes 1 hour 33 minutes to complete. This easy route features mostly paved surfaces and passes through natural preserves.
  • Another top favourite among local touring cyclists is Grosse Point Lighthouse – Green Bay Trail loop from Lake Forest, a moderate 41.1 miles (66.2 km) path. This route utilizes the Green Bay Trail, offering views towards Lake Michigan and the Grosse Point Lighthouse.
  • Local touring cyclists also love the Skokie Lagoons – North Branch Trail loop from Fort Sheridan, a 33.3 miles (53.6 km) trail leading through the Skokie Lagoons and North Branch Trail, often completed in about 3 hours 21 minutes.
  • Touring cycling around Highland Park is defined by paved bikeways, forest preserves, and river paths. The network offers options for different ability levels, from easy loops to moderate distances.
  • The routes in Highland Park are highly rated by the komoot community with an average score of 4.8 stars from over 80 reviews. More than 500 touring cyclists have used komoot to explore Highland Park's varied terrain.

Last updated: May 29, 2026

5.0

(9)

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#1.

Small Lake – Skokie Valley Bikeway loop from Fort Sheridan

43.2km

02:31

130m

130m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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5.0

(1)

12

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Tips from the Community

mtm05005
May 9, 2025, General Sheridan Equestrian Statue

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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oliviakellis
February 13, 2024, Green Bay Trail

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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oliviakellis
January 23, 2024, Erickson Woods

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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Frequently Asked Questions

How many touring cycling routes are available in Highland Park?

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.

What kind of terrain can I expect on touring cycling routes in Highland Park?

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.

Are there any easy or family-friendly touring cycling routes in Highland Park?

Yes, Highland Park offers many easy routes suitable for families and beginners. For instance, the North Branch Black Paved Trail – 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.

What natural features or landmarks can I see along the touring cycling routes?

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.

Are there any circular touring cycling routes in Highland Park?

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 – Green Bay Trail loop from Lake Forest and the Small Lake – Skokie Valley Bikeway loop from Fort Sheridan.

What is the best time of year for touring cycling in Highland Park?

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.

Are dogs allowed on the touring cycling routes in Highland Park?

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.

Where can I park when accessing touring cycling routes in Highland Park?

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.

What are some longer touring cycling routes for more experienced riders?

For those seeking longer rides, the Grosse Point Lighthouse – 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 – North Branch Trail loop from Fort Sheridan, which is 33.3 miles (53.6 km).

What do other touring cyclists enjoy most about cycling in Highland Park?

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.

Are there any routes that connect to Lake Michigan?

Yes, some routes utilize the Green Bay Trail, which offers views towards Lake Michigan. For example, the Grosse Point Lighthouse – Green Bay Trail loop from Lake Forest provides opportunities to experience the lake's proximity and views.

How long do touring cycling routes in Highland Park typically take to complete?

The duration varies significantly by route and your cycling pace. Easy routes like the North Branch Black Paved Trail – North Branch Trail loop from Hubbard Woods can take around 1 hour 33 minutes. Longer, moderate routes such as the Skokie Lagoons – North Branch Trail loop from Fort Sheridan might take approximately 3 hours 21 minutes.

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