Demolition Derby - June - This "crash em up" derby is held at the Perry County Fairgrounds.
Perry County Fair-June - The oldest continuous fair in Illinois, the Perry County Fair held mid-June, has a variety of events and activities. It is located at the Perry County Fairgrounds.
St Bruno's Parish Picnic- July - This annual picnic, held on the grounds of the Pinckneyville K of C Hall is a major fundraiser for St Bruno's Parish. With Music, Dancing, Bingo, Food, and games, this fun for all picnic is held on the third Saturday in July.
ATA Steam Gas & Power Show- Aug- Located at the Perry County Fairgrounds on the third weekend in August this show put on by the American Thresherman Association has a variety of events including tractor pulls, truck pulls, and even horse pulls!
City Wide Yard Sale- 3rd weekend in Aug- Sponsored by the Chamber of Commerce this City Wide event held in conjunction with the ATA show will help you sell your treasures and find new ones.
American Thresherman Fall Show- Oct - Similar to the August show this Fall show is also put on by the American Thresherman Association the third weekend in October includes tractor pulls and much more!
Mardi Gras (fall festival)- Oct -The Pinckneyville Chamber of Commerce is the proud organizer of the area's largest Halloween Festival. Join us for a flea market, wine tasting, car show and spectacular night time parade the last Saturday in October.
Duster Thomas Hoops Classic- Dec - Holiday Basketball tournament held at the Thomas Gym in remembrance of Duster Thomas between Christmas and New Year's Eve.