Main Events

17TH ANNUAL WINE'N ON THE CHISHOLM TRAIL FESTIVAL Annually held the second weekend in September This two-day event is held on Friday, Sept. 13th, 2024 and Saturday, Sept. 14th, 2024. Friday, September 13th 6-10 PM, dinner will be served from 6:30-9 PM. Tickets for Friday's Italian-style dinner under the Oklahoma stars can be purchased at...

Join us for the last Friday night Car Cruise of 2024! Due to the Car Show cancellation in April, we will be hosting a mini/ modified Car Show as well.     Friday, September 20, 20246:00p.m. - 9:30p.m. *Entry Fees: $20 Car Show Entry & Cruise / $15 Cruise Only* Event Schedule 6pm-7:30pm - Car...

Saturday, October 26th, 2024 – 11 AM - 1 PM Join us for the annual Main Street Duncan Boo Review. Saturday, October 26th 11am – 1pm. Kid’s Costume Contest will take place at 12noon in the parking lot next to the Palace Theatre. And of course, Main Street Merchants will have trick or treating for...

November 16, 2024 – 4 PM - 8 PM Holiday Stroll will be Saturday, November 16 from 4-8 PM in historic downtown Duncan, Oklahoma. You’ll definitely want to visit downtown Duncan and #shoplocal as the restaurants, boutiques, and store fronts that are offering new merchandise, discounts, gift with purchase and more! Each store has something...

March 21, 2025- CANCELLED It is with great regret that Main Street Duncan announces the cancellation of the upcoming March 21 Friday Night Car Cruise. Due to the significant increase in insurance coverage costs, driven in part by recent tragic events in New Orleans and other locations, insurance providers are pricing the cost of this...

May 3, 2025 – 10:00 AM - 4:00 PM Main Street Duncan Spring Stroll – Explore all the amazing offerings from local merchants and find somethingspecial for the incredible women in your life! 🌸👗💐  

🛍 Sip & Shop on Main Street Duncan 🛍 Main Street is about to come alive with cozy vibes, local sips and fabulous finds at this season’s must-attend event: 🗓️ Date: May 30th 📍 Where: Main Street Duncan ⏰ Time: 6-9pm   Grab your friends, a cute tote bag, and your shopping spirit because we’re...