Grady County Free Fair
Annual Grady County Free Fair — Aug 27–29, 2026 — carnival, livestock and junior shows, contests, vendors and family activities at the Grady County Fairgrounds (500 E Choctaw Ave., Chickasha).
2026 Wings and Wheels
Affiliate disclosure: As an Amazon Associate I earn from qualifying purchases. Amazon links below are paid links; links marked “search” open Amazon search results. Chickasha’s Wings & Wheels Will Bring […]
Christmas in July — CoolDown Block Party (Downtown Chickasha)
A free family-friendly CoolDown Block Party in downtown Chickasha with water slides, a foam party, Cycle Santa, snow cones and a movie under the stars — Saturday, July 25, 2026, 6:00–9:00 PM.
Southwest Oklahoma Vintage Toy Show
500 E Choctaw Ave.
HOYRA Youth Rodeo
500 E Choctaw Ave.
Rock Island Ride 2025
The Rock Island Ride offers scenic cycling routes of 10, 30, 50, and 62 miles through Grady County. All routes start and finish at the historic Rock Island Depot in […]
Rock Island Arts Festival 2025
The Rock Island Arts Festival transforms downtown Chickasha into a vibrant celebration of art, music, and culture. Browse artist booths, enjoy live performances, savor food‑truck fare, and explore hands‑on activities […]
Oklahoma Food Truck Championship 2025
Over 30 of Oklahoma’s best food trucks will compete for $10,000 in cash prizes during the 8th Annual Oklahoma Food Truck Championship in downtown Chickasha. Enjoy delicious eats, live music, […]
Rock Island Weekend 2025
Rock Island Weekend is a two-day celebration featuring the Rock Island Arts Festival, Rock Island Ride, live music, food trucks, art vendors, family activities, and more along historic Chickasha Avenue. […]
Grady County Fair 2025
Established in 1915, the Grady County Fair is a three-day celebration of agriculture, education, and family fun. Held at the Grady County Fairgrounds in Chickasha, Oklahoma, the 2025 fair will […]