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Print Friendly MapThe Waubonsie Trail links Boulder Hill and the Village of Oswego via a greenway corridor within a residential community. The eastern trailhead is in Jaycee Park, which offers a playground, picnic shelter and open areas for sports practice.
Old Post Elementary School and Thompson Junior High School are also along the trail, making it a safe route to school for the area’s residents. A short designated on-road route on Brockway Drive, Eastway Drive and Ashlawn Avenue leads to the western section of trail just south of the Civic Center and Aquatic Park.
After crossing active railroad tracks, the Waubonsie Trail enters Eagle Ridge Park and Violet Patch Park. The former features a disc golf course, while the latter is a great place for fishing, boating or picnicking along the Fox River. The trail ends at the Fox River Trail, a 43-mile greenway that originates in the south in Oswego.
Parking for the Waubonsie Trail can be found at the Civic Center and Aquatic Park on Ashlawn Avenue; Thompson Junior High School on Boulder Hill Pass; Chesterfield Park on Chesterfield Avenue; Pearce’s Ford Park on Pearce’s Ford Drive; Old Post Park and Old Post Elementary School on Old Post Road; and Jaycee Park on Saugatuck Road.
While some sections are a little bumpy and a lot of the trail is near people’s backyards, it does provide very nice views and is pretty fun to ride. Very easy to access as both endpoints have parking lots and many sidewalks connect to the trail. Safe to say this is one of the best in Oswego.
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