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Routes
Road cycling routes
United States
Illinois
Lake County

Highland Park

The best road cycling routes around Highland Park

4.8

(120)

1,442

riders

48

rides

Road cycling routes around Highland Park, Illinois, primarily navigate a landscape shaped by former golf courses, restored woodlands, and interconnected trail systems. The region features green lawns, native gardens, and various wetland and riverfront habitats, offering varied topography for cyclists. Paved paths, such as the Half Day Road Bike Path, include sections with elevation changes, while multi-use trails connect to wider regional networks.

Best road cycling routes around Highland Park

  • The most popular road cycling route is Fort Sheridan Pond…

Last updated: July 1, 2026

83

riders

#1.

Shelton Park – Founders Park loop from Braeside

51.1km

02:10

130m

130m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Tips from the Community

oliviakellis
June 22, 2025, Fort Sheridan Forest Preserve

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 is the house where the movie Home Alone was filmed—a fun spot to stop by and remember this iconic film before continuing your ride.

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A small, family-friendly park along the Green Bay Trail that’s a good place to stop and recharge. It has shaded grassy areas—perfect for a quick break.

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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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Christ Church has a beautiful courtyard that is open to the public. As this is a place of worship, if you decide to stop to check it out, make sure you are respectful.

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Lake Front Park is a beautiful small park next to Glencoe Beach. There is a large lawn area that is a great spot for a break.

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mtm05005
December 9, 2024, Founders Park

Founders Park is a small, urban park in Glencoe. It has ball fields, picnic tables, a playground and restrooms.

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Alex
February 13, 2024, Fort Sheridan Pond

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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Frequently Asked Questions

How many road cycling routes are available in Highland Park?

Highland Park offers a selection of 14 road cycling routes, catering to various skill levels. These routes are highly rated by the komoot community, with an average score of 4.7 stars.

What kind of terrain and scenery can I expect on road cycling routes in Highland Park?

Road cycling routes in Highland Park, Illinois, primarily navigate a landscape shaped by former golf courses, restored woodlands, and interconnected trail systems. You'll encounter green lawns, native gardens, and various wetland and riverfront habitats. The topography offers varied experiences, from paved paths with elevation changes, like the Half Day Road Bike Path, to multi-use trails connecting to wider regional networks.

Are there routes suitable for beginners or families in Highland Park?

Yes, Highland Park offers several easy road cycling routes perfect for beginners or families. For instance, the Northcroft Park – Skokie Valley Bikeway loop from Highland Park is an easy 21.9-mile path offering a smooth ride through local parks and along the bikeway. There are 8 easy routes in total.

Are there any challenging routes for experienced road cyclists in Highland Park?

While Highland Park's routes are generally easy to moderate, experienced cyclists can find longer, moderate options to extend their rides. The Fort Sheridan Pond – Skokie Valley Bikeway loop from Ravinia is a moderate 27.3-mile trail featuring varied terrain along the Skokie Valley Bikeway, providing a good workout. There are 6 moderate routes available.

What are the typical distances for road cycling routes in Highland Park?

Road cycling routes in Highland Park vary in distance, with options ranging from shorter loops to longer excursions. You can find routes like the Skokie Lagoons – Skokie Lagoon No. 3 loop from Ravinia Park at 15.6 miles, up to the 27.3-mile Fort Sheridan Pond – Skokie Valley Bikeway loop from Ravinia.

Are there any loop road cycling routes available in Highland Park?

Yes, many of the road cycling routes in Highland Park are designed as loops, offering convenient starting and ending points. Examples include the Fort Sheridan Pond – Skokie Valley Bikeway loop from Ravinia and the Founders Park – Shelton Park loop from Highland Park.

What points of interest or landmarks can I see along the road cycling routes?

Along the road cycling routes, you can explore various natural and scenic points of interest. Notable attractions include the tranquil Skokie Lagoon No. 3, the picturesque Half Day Forest Preserve Ponds, and the expansive MacArthur Woods Forest Preserve. Many routes also incorporate sections of the North Branch Trail.

Where can I find parking for road cycling trails near Highland Park?

Parking is generally available at various access points to the trail systems and parks in and around Highland Park. Many routes start from locations like Ravinia or Highland Park itself, where public parking facilities are often present. Specific parking details can usually be found on individual route pages or local park district websites.

Are there any permits required for road cycling in Highland Park?

Generally, no specific permits are required for road cycling on public trails and bikeways in Highland Park. The city actively promotes cycling and pedestrian activities, with a focus on creating a comprehensive and connected non-motorized transportation system for public enjoyment.

What is The Preserve of Highland Park and how does it relate to cycling?

The Preserve of Highland Park is a 100-acre area developed from a former golf course, featuring green lawns, native gardens, and restored woodlands. It offers walking and biking trails that connect to neighborhoods and regional biking trails. The Preserve's trails incorporate interesting topography from the former golf course, providing a unique cycling experience. More information can be found on the Visit Lake County website.

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

The area is highly rated by the komoot community, with an average score of 4.7 stars from over 19 reviews. Reviewers often praise the interconnected bikeways, the varied topography from former golf courses, and the scenic beauty of restored woodlands and wetland habitats. The network offers options for different ability levels, from easy loops to moderate challenges.

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