Sleepy Hollow Park, Highland Park, IL

Sleepy Hollow Park in Highland Park spans 17 acres of rolling terrain anchored by a large pond that attracts waterfowl and offers a quiet backdrop for residents. A 1.3-mile paved loop accommodates walking, jogging, and cycling, while an adjacent crushed-stone path branches through wooded sections and connects to the larger Skokie Valley Trail system. Picnic shelters, a playground with modern equipment, and restrooms sit near the main parking area, and a sledding hill draws families after winter snowfall. The park’s southern edge borders the Metra Union Pacific North Line, placing downtown Highland Park’s shops and dining within a 10-minute walk and providing direct rail access to Chicago. Open lawns and mature trees create space for informal sports, and seasonal programs run by the Park District of Highland Park—such as outdoor fitness classes and nature walks—take place on site. The combination of maintained trails, varied recreation options, and convenient transit links makes Sleepy Hollow Park a practical daily resource for Highland Park homeowners.

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