2026 will be a great year for entertainment at the Grandstands! Explore the daily schedule below for more details!
Tuesday, July 21- Midwest Summer Nationals Tractor Pulls
Midwest Summer Nationals Tractor & Truck Pull – July 21 at 6pm at the Stephenson County Fair in Freeport, IL. This NTPA Region III event features Super Farms, Limited Light Super Stocks, 4.1 Pro Stocks, 3.6 Diesel Trucks, and Light Super Stocks. An FFA Truck & Tractor Pull kicks things off at 12pm. Admission is free with a $10 fair entry, and pit passes are $20. Located at 2250 S Walnut Rd, Freeport, IL 61032.
For more details on Tractor Pulls:
Wednesday, July 22- Big Hat Rodeo and Wildwood Country
Big Hat Rodeo – 2026 Trailblazers Tour at the Stephenson County Fair! Join us Wednesday, July 22nd at 6:00 PM for an action-packed evening featuring bareback riding, tie down roping, girls breakaway roping, steer wrestling, saddle bronc riding, team roping, cowgirls barrel racing, bull riding, and a bucking horse finale. Free grandstand seating with $10 gate admission.
Wildwood Country – Live at the Stephenson County Fair
Get ready to two-step under the stars! Wildwood Country brings their high-energy All-American sound to the Community Entertainment Tent on Wednesday, July 22 at 8:00 PM — right after the Rodeo.
Blending the best of old and new country, country rock, and line dance favorites, Wildwood Country delivers a live show that keeps the whole crowd moving. Whether you’re a lifelong country fan or just looking for a great night out at the fair, this is one performance you won’t want to miss.
Free with fair admission. Show begins at 8:00 PM following the Rodeo.
Thursday, July 23- Carquest Auto Parts Tough Truck Challenge
Tough Truck Challenge
The 2026 Tough Challenge is coming to the Stephenson County Fair on July 23! Cars, trucks, vans, jeeps, SUVs, and side by sides — register early online for $35 before July 13. Limited entries, cash prizes, starts at 8 PM. Presented by Carquest Auto Parts.
For more information & registration for Carquest Auto Parts Tough Challenge:
Friday, July 24- Friday Fair Music Fest
Friday Fair Music Fest
Friday Fair Music Fest – Free Concerts in the Grandstand!
Friday night at the Stephenson County Fair is all about live music! Find a seat with friends and family in the grandstand and enjoy two great concerts — completely free with fair admission.
The evening kicks off at 5:30 PM with the Rock Steady Band, setting the stage for a night to remember. Then at 8:00 PM, the Richrath Project REO takes over with a powerhouse tribute to the legendary rock band REO Speedwagon. Featuring the iconic guitar work that defined a generation of rock, this concert will have you singing along all night long.
Free with fair admission. Find your spot in the grandstand early!
For more Concert Details:
Saturday, July 25- Demolition Derby
Demolition Derby
Get ready for DESTRUCTION! Robbo’s Xtreme Derby is coming to the Stephenson County Fair — Saturday, July 25 at 6PM! Kid’s Power Wheels, Mini Van/SUV, Pro-Stocks, Young Guns, Bonestock Compacts & MWFA Class. Bring the whole family for an explosive night of smashing, crashing, and non-stop action!
For more details: