Annual Events
- • Auto Swap Meet- Feb
- - Indoor/Outdoor automotive parts swap meet and car corral, event admission is $3.00. All types of automotive parts will be there, stock cars, drag cars, classic cars, and racing collectibles. Always held the second Sunday in February and is located at the Perry County Fairgrounds.
- • Farmers Market- May-Oct
- - Occurs every Tuesday May through October, and is now located in the Trinity Assembly of God parking lot from 3:00 P.M. to 6:00 P.M. Lots of fresh, in season, locally grown fruits and veggies, home made gifts, art, flowers and baked goods.
- • Demolition Derby-May&Oct
- -Held the first Friday in May and October. 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.
- • IL Rural Heritage Museum's Annual Tractor Drive-June
- -Drive your tractor through the more scenic route of Pinckneyville and come back for a great home cooked dinner! This event is a great fundraiser for the IL Rural Heritage Museum.
- • Collectors Caravan-June
- -Surrounds the Perry County Courthouse bringing in people from neighboring communities to share the enjoyment of antiques and collectibles, annuals and perennials, and arts and crafts.
- • 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.
- • Family Night in the Park-July
- - Held the last Friday in July this event is put on by the Pinckneyville Police Department, Fire Department, and Ambulance Service. Free food and drinks, and actives for the entire family ranging from a magic show to a Police officer donut eating contest.
- • 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 races!
- • City Wide Yard Sale- Aug
- - Sponsored by the Chamber of Commerence this City Wide event held August 20th to the 21st will help you sell your treasures and find new ones.
- • Old Time Icecream Social- Sept
- -Love Icecream AND Socializing? Perfect, September 11th we invite you to Pinckneyville Junior High School for homemade ice cream, fruit cobblers and gospel and bluegrass music.
- • Pinckneyville Fall Classic 8K Run- Oct
- -This run is a USATF certified course and is held at the Perry County Fairgrounds. Includes a free T-shirt, attendance prizes, refreshments, and awards following the race.
- • American Thresherman Fall Show- Oct
- - Similar to the August show this Fall show is also put on by the American Thresherman Association on October 15-17, includes tractor pulls and much more!
- • Mardi Gras (Homecoming)- 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.
- • Masquerade Party and Silent Auction- Oct
- - Held at the Exposition Hall in the Perry County Fairgrounds,this event is a major fundraiser for the Foundation for Pinckneyville. Come enjoy a jazz band, delicious hors d’oeuvres and desserts, hilarious costumes, prizes, and an auction of donated items.
- • Duster Thomas Hoops Classic- Dec
- - Holiday Basketball tournament held at the Thomas Gym in remembrance of Duster Thomas.