Sycamore Pumpkin Festival is a family festival on the last full week of October Annually. The festival promotes awareness of the City of Sycamore, and provides an opportunity for DeKalb County not-for-profit organizations to participate in fund raising activities, community education and enrichment.

The festival has over 1000 entries in the Lions Decorated Pumpkin Display on the Historic Courthouse Lawn, 2 carnivals, many non-profit vendors, two indoor craft shows, entertainment and various activities, and it concludes with a 10K Run, a Family Fun Run, and a parade on Sunday.