Cruisin' the Chisholm Trail Car Show: April 17th and 18th HAS NOT BEEN POSTPONED

Wine'n on the Chisholm Trail Festival


Annually held the second weekend in September

This two-day event is held on Friday, Sept. 11th, 2020 and Saturday, Sept. 12th, 2020

Friday, September 11th

5-10 PM, dinner will be served from 6-9 PM. Tickets for Friday's Italian-style dinner under the Oklahoma stars is encouraged as tickets will sell out. To purchase tickets, please click the Purchase Tickets button on this page. We will offer a gourmet 3-course meal which includes the signature wine glass for samples from all of the  Oklahoma wineries while enjoying live musical entertainment. 

Saturday, September 12th

Noon to 6 PM, enjoy samples from all of the Oklahoma wineries with the purchase of our signature wine glass for $10. Vendors will be onsite, live demonstrations, and food trucks are available all day. Live performances will be announced. This event has a separate close-by area for those under the age of 21


10th and Main St in downtown Duncan, Oklahoma in the southeast corner of the intersection located under the 'Crapemyrtle Mural'. 

For GPS Directions, please enter the following address: 926 W. Main St. Duncan, Ok 73533. 

From OKC: southbound on I-44, take exit 80 in Chickasha to access HWY 81 south. Continue south to Duncan, turn east on Main St. 

Contact Us

Vendor Details

Vendor deadline Aug. 21st 

Purchase Tickets

Wine'n on the Chisholm Trail Dinner Tickets: Friday, Sept. 11th, 6-9 PM

Pay with PayPal or a debit/credit card