Sycamore: Festivals, History, and Trails

Sycamore offers several distinct reasons to visit: the annual fall Pumpkin Festival, the DeKalb County History Center, and trails for biking, walking, and running. If you’re looking for a hotel, first consider which focus best suits your stay: a full festival program, the history of DeKalb County, or outdoor activity on trails through Sycamore and DeKalb.

The Sycamore Pumpkin Festival in Fall

The Sycamore Pumpkin Festival is an annual fall festival geared toward families. It takes place downtown near the intersections of Main Street and State Street; many of the festivities are held on the courthouse lawn and the surrounding town square. Specific locations may change from one year to another. If you’re traveling for the festival, check the dates and program for the relevant year.

The program includes more than 1,000 entries in the Lions Club Decorated Pumpkin Display, two carnivals, and three indoor arts and crafts shows. There is also Saturday entertainment, a variety of activities, and a 90-minute parade on Sunday to close out the festival. The scope of the program may vary from year to year.

DeKalb County History

The DeKalb County History Center in Sycamore focuses on the history of DeKalb County. It combines exhibits and programs with research; research archives and a collection devoted to preserving the county’s past are also part of the Center. The Center also has an outdoor picnic area and on-site parking. Since these facilities may change, check their current status before your visit.

Trails through Sycamore and the Surrounding Area

The Sycamore/DeKalb Trail includes 17 miles of paved trails for biking, walking, and running through Sycamore and DeKalb. At its eastern end in Sycamore, it connects to the Great Western Trail. The Great Western Trail is a rails-to-trails route that runs 18 miles from St. Charles to Sycamore through the surrounding area, passing numerous small streams and wetlands.

The comparison highlights their different features: the Sycamore/DeKalb Trail offers paved trails through two communities for several types of use, while the Great Western Trail passes through countryside with streams and wetlands. Check current route information if you’re planning a specific trip, as details may change.

The Kishwaukee River is 63 miles long and flows directly through Sycamore.

Summer Market and Travel Season

The Sycamore Farmers' Market brings together farmers and small businesses from Sycamore and the surrounding area every week in summer. Alongside the fall Pumpkin Festival, this offers a seasonal contrast: the market is a weekly summer event, while the festival is an annual fall celebration. Since the market’s seasonal schedule may change, check current information if you’re planning your trip around a market day.

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