From chili cook-offs and historic tours to legendary racing, fall events in Randolph County offer plenty of reasons to hit the road. Just across the Ohio border, this eastern Indiana county keeps the calendar full all season long.
Winchester 400 Weekend Brings High-Speed Action
Racing fans know October means one thing at Winchester Speedway. The 55th Winchester 400 Weekend returns October 8 through 11, bringing four days of racing to one of the country’s most legendary short tracks.
Known as “The World’s Fastest Half Mile,” Winchester Speedway has challenged drivers for decades with steep turns and high speeds. During Winchester 400 Weekend, fans gather for several days of racing, cheering on drivers,s and enjoying one of the area’s biggest fall events. Even visitors new to racing often get caught up in the excitement once the engines fire up.
Historic Tours and Paranormal Activity in Randolph County
The Randolph County Asylum offers one of Randolph County’s most talked-about attractions. Originally built as an infirmary, the historic property now attracts visitors interested in architecture, local history, and the paranormal.
Visitors can take guided history tours to learn about the building and the people who once lived there. Overnight flashlight tours give guests access after dark, when the atmosphere feels entirely different. The asylum has also hosted television shows, including Paranormal Lockdown, Destination Fear, and Kindred Spirits.
The location has also gained national attention, appearing on television shows including Paranormal Lockdown, Destination Fear, and Kindred Spirits. Today, the property also hosts photography sessions, weddings, special events, and overnight guests, with nearly 60,000 square feet to experience.
Farmland Chili Cook Off Festival
Fall also brings one of the area’s favorite traditions. On Saturday, September 26, the Farmland Chili Cook Off Festival fills the Farmland Community Building with live entertainment, family activities, and plenty of chili.
Event Details:
- Date: Saturday, September 26, 2026
- Location: Farmland Community Building, 100 N. Main Street, Farmland, Indiana
- Chili Service: 11:30 a.m. to 1 p.m.
- Pie Auction: Begins at 1:15 p.m
Visitors sample recipes while enjoying a relaxed afternoon in the heart of the community. The smell of simmering chili and the sounds of music make it an easy stop during a fall drive through Randolph County.
Start Planning Your Fall Trip to Randolph County, IN Today
From race day traditions and historic sites to hometown festivals, Randolph County, Indiana, fall events offer several reasons to plan a seasonal getaway. Plan your visit today at www.randolphcountytourism.com.
