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Jogging around Highland Park, Illinois, offers diverse landscapes for runners. The region is characterized by a mix of paved trails, natural woodlands, open prairies, and scenic bluffs overlooking Lake Michigan. Many running routes follow the shoreline or wind through restored natural areas, providing varied terrain. Highland Park sits on a high plateau formed by a glacial moraine, offering elevated views.
Last updated: May 10, 2026
28
runners
22.6km
02:20
110m
110m
Jog this difficult 14.0 miles (22.6 km) loop through Fort Sheridan Forest Preserve and along the Green Bay Trail, featuring lake views and d
3.97km
00:25
20m
20m
Jog the easy 2.5-mile Foley's Pond loop via Green Bay Road in Highland Park, offering scenic views around a historic pond.

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14
runners
5.35km
00:33
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
12
runners
7.04km
00:49
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
runners
7.92km
00:56
10m
10m
Moderate run. Good fitness required. 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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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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Experience the allure of Rosewood Beach, a nationally acclaimed destination offering diverse amenities. Discover a nature cove for ecological programs, a guarded swimming beach, and a recreation beach. Nestled against wooded bluffs, the beach boasts a unique Interpretive Center, along with amenities like concessions, restrooms, and a guard building connected by a charming boardwalk.
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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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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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Discover the enchanting history of Foley's Pond, once a Foley family brickyard, in 1897. Originally a clay mining site, the pond emerged when an underground spring filled the excavated hole. Purchased by the Park District in 1925, the pond became home to bass, perch, and pickerel. In the 1930s and 1940s, wild canaries adorned the trees around Foley's Pond. Situated between Sunset Valley Golf Course's first and second holes, Foley's Pond offers a unique blend of history and natural serenity.
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Boots were a must with the mostly ice covered surface. I'll have to check the trail again in a week. I'm hoping it'll all melt this week.
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Running on ice and snow wasn't easy. Altra Lone Peak Mid RSM was ide
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Highland Park, Illinois, offers a wide selection of running routes, with over 90 options available for joggers. These routes cater to various preferences, from easy loops to more challenging long-distance runs.
The jogging trails in Highland Park, Illinois, feature diverse terrain. You'll find a mix of paved multi-use trails, natural woodlands, open prairies, and scenic bluffs overlooking Lake Michigan. Routes like the Fort Sheridan and Green Bay Trail Loop combine coastal views with stretches through wooded and open areas, while the Fort Sheridan Birding Trail Loop leads through varied ecosystems.
Yes, Highland Park has several easy running routes perfect for beginners or those looking for a relaxed jog. An excellent option is the Foley's Pond loop via Green Bay Road, an easy 2.5-mile path offering scenic views around a historic pond. The Fort Sheridan Birding Trail Loop is another easy 2.1-mile trail through varied ecosystems.
For those seeking longer runs, the Fort Sheridan and Green Bay Trail Loop is a popular choice, spanning 14.0 miles (22.6 km). The Green Bay Trail itself is a 9-mile paved route that can be extended, offering segments up to 10 miles for a more challenging endurance run.
Jogging in Highland Park offers views of several natural and historical features. You can enjoy stunning views of Lake Michigan along trails in the Fort Sheridan Forest Preserve and Moraine Park. The Green Bay Trail provides optional side trips to beachfront views. Other notable spots include the historic Foley's Pond and the diverse ecosystems within the Fort Sheridan Forest Preserve. Nearby attractions include Skokie Lagoon No. 3 and the Des Plaines River bridge.
Yes, many of the running routes in Highland Park are designed as loops, offering convenient circular options. Examples include the Fort Sheridan and Green Bay Trail Loop, the Fort Sheridan Birding Trail Loop, and the Foley's Pond loop via Green Bay Road. The Running loop from Highland Park is another popular circular option.
The running routes in Highland Park are highly regarded by the komoot community, holding an average rating of 4.0 stars from 3 reviews. Runners often praise the diverse landscapes, from coastal views to woodlands, and the variety of options available for different fitness levels.
While specific family-friendly designations are not always explicit, many trails in Highland Park are suitable for families due to their varied lengths and difficulty levels. The paved Green Bay Trail, with its community parks, and easy loops like the Foley's Pond loop, are generally good options for families looking for a gentle outdoor activity.
Many parks and trails in Highland Park, Illinois, are dog-friendly, though specific regulations may vary by location. It's generally advisable to keep dogs on a leash and clean up after them. Areas like the Fort Sheridan Forest Preserve and the Green Bay Trail are popular spots where you'll often see other dog walkers and runners.
Yes, public transport is an option for accessing some running trails in Highland Park, Illinois. The Green Bay Trail, for instance, conveniently parallels Chicago's Metra commuter rail line, making it accessible via train for those coming from other North Shore towns or Chicago.
Parking is generally available at various access points for the running trails in Highland Park. For trails within forest preserves like Fort Sheridan, designated parking lots are typically provided. For routes along the Green Bay Trail or in community parks, street parking or small lots may be available. It's recommended to check specific park websites for detailed parking information.
Yes, Highland Park is known for its commitment to preserving natural spaces. The Preserve of Highland Park, a 100-acre natural area on a former golf course, features restored woodlands, native gardens, and trails. Many running routes also wind through natural woodlands and open prairies within the various parks and preserves.


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