Southwest Oklahoma Premier Wine Festival: ‘Wine’n on the Chisholm Trail Festival’

September 05, 2019

The 13th annual Wine’n on the Chisholm Trail Festival is slated for this weekend, Sept. 6th and 7th, in historic downtown Duncan, Oklahoma.

Main Street Duncan has hosts the annual event to provide benefits and grants to the small businesses in downtown Duncan. Over two days, over 500 people will enter the festival to purchase Oklahoma wines, enjoy food, vendors, and a variety of activities. On Friday, the organization hosts an Italian-style dinner under the Oklahoma stars at 10th and Main St. Always improving the festival each year, The Merchant has been asked to prepare and cater the meal on Friday, Sept 6th from 6-9 PM though the event will continue from 5-10 PM on Friday and Noon to 8 PM on Saturday, Sept. 7th.

“We have watched this event grow,” said Kristin Arrington, Wine Festival Co-Chairperson, “and we’re thrilled to host the wine festival in downtown Duncan for the fourth year now as we will continue to do with the support of the City and Main Street merchants.”

The event has grown to include multiple vendors, food and wine pairings, live entertainment and more. Festival hosts say, like last year, the many downtown merchants will offer deep discounts to festival participants so shopping downtown will also take place on Saturday. New this year will be a silent auction of sorts on Friday evening. The Balloon Pop allows festival participants a chance to win a prize valued between $50-$100 for a $20 donation. Only 25 balloons will be sold and prizes range from a $100 from Eclectic Echo to $100 to Byford Auto Group.

“The organization exclusively hosts this annual event in order to be able to provide the many benefits available to our business members ,” said Main Street Duncan Executive Director Destiny Ahlfenger, “like the paint grants, micro-signage grants and the new vibrancy grant to enhance downtown Duncan.”

Friday’s dinner is $30/person and includes the customary three-course meal while Saturday only costs $10. Food trucks will be available on Saturday throughout the day as well as downtown Duncan’s multiple delicious restaurants and eateries. To learn more about Wine’n on the Chisholm Trail Festival, contact the Main Street Duncan office at 580.252.8696 or visit the website at for information. Tickets are required for Friday’s dinner will sell out so purchasing tickets early is encouraged.

Main Street Duncan is a 501(c)3 charity and all donations are fully tax-deductible to the extent of federal and state tax laws; the program has been affiliated with the Oklahoma Main Street Center and nationally accredited through the National Trust for Historical Preservation since 1986.