Main Street Duncan

Holiday Stroll 2025
2025-11-22 16:00 - 20:00 (America/Chicago) | Main Street Duncan, 828 W Main St B, Duncan, OK, 73533, United States
November 22, 2025 – 4 PM – 8 PM

✨ Holiday Stroll ✨Saturday, November 22 | 4–8 PM📍 Historic Downtown Duncan, Oklahoma
Kick off the holiday season in the heart of downtown Duncan! 🎄 Stroll Main Street, explore your favorite boutiques and storefronts, while shopping local and discovering new merchandise, exclusive discounts, gifts with purchase, and so much more! 🎁
Santa will be located at the Duncan Tower Shoppes & Offices beginning at 6pm. Pictures will be provided by DD Visuals.
Each Main Street District merchant has something special — from festive treats to unique holiday finds — so be sure to stop in and see what’s merry and bright. 🌟
We can’t wait to see you downtown for the Holiday Stroll! 🛍️❤️
We are no longer accepting vendor applications.

Shop Small Saturday 2025
2025-11-29 08:00 - 17:00 | Main Street Duncan, 828 W Main St B, Duncan, OK, 73533, United States
Main Street Duncan reminds the community to Shop Small, Saturday, Nov. 29

Duncan Christmas Parade 2025
2025-12-06 15:00 - 17:00 | Main Street Duncan, 828 W Main St B, Duncan, OK, 73533, United States
Saturday, December 6, 2025 – 3:00 PM
🎄 Duncan Christmas Parade! 🎄
Get ready to bring the holiday cheer — the Duncan Christmas Parade is just around the corner!
✨ Theme: Toyland Christmas📌 Staging details will be provided 1 week of the parade.
🗺️ Traditional parade route utilizing Walnut Ave. & 7th St.
Parade application is no longer available. Please contact the Main Street Duncan office at 580.252.8696

Flash. Mob. Shop on Main! Over $500 in Giveaways and Prizes - FREE Event!
2026-03-05 17:00 - 20:00 | Think Ability Garden Market, 805 W Main Street, Duncan, OK, 73533, United States
NOW over $35 per bag prizes and $500 in giveaways! THIS EVENT KEEPS GROWING! All you have to do is show up and Flash. Mob. Shop on Main!
Bring your friends to Think Ability Garden Market enjoy FREE wine samplings from Cotton Blossom Winery selections and enjoy 20% OFF STOREWIDE, samplings, treats and more!
Be one of the FIRST 50 SHOPPERS to guarantee your bag 🙂

Spring Stroll on Main Street - Over $500 in prizes!
2026-04-11 10:00 - 17:00 | Main Street Duncan, 828 W Main St B, Duncan, OK, 73533, United States
Shop your favorite Main Street merchant for special savings, giveaways and goodies! Get a sticker package with purchase (while supplies last) and you might just get one that has the “Golden Sticker” which means you’ve won one of our Grand Prizes from Main Street Duncan 🙂
Start shopping early, event is 10am-5pm (or merchant’s regular hours) for the best chance at over $500 in prizes!!
(If severe weather occurs, rain date is 4/18)
https://mainstreetduncan.com/wp-content/uploads/2026/04/Spring-Stroll-video1.mp4

Flash. Mob. Shop on Main! Over $500 in giveaways and prizes - FREE event!
2026-04-23 16:00 - 19:00 | Vintage Treasures, 910 W Main Street, Duncan, OK, 73533, United States
$25 in goodies in EVERY FREE SHOPPER BAG and $500 in giveaways! This event keeps growing in goodies. All you have to do is show up and Flash. Mob. Shop on Main! Bring your friends to Vintage Treasures enjoy special savings and freebies! Be one of the FIRST 50 SHOPPERS to guarantee your bag 🙂

Chisholm Trail Car Show POKER RUN! Fun on The Trail before the Car Show :)
2026-06-05 17:00 - 20:00 | OK
This is your ‘fun on The Trail’ before the car show begins! Come and join us for a Poker Run full of fun and ending with great prizes at Kochendorfer Brewery. Registration begins at 5pm til 6:30pm and ends at the Brewery at 8pm where you will meet up with new and old friends and maybe even claim your part of some great prizes. You will also have the opportunity to pre-register for “Thunder on the Trail” the next day. Only $10 per hand – no limit and kid’s can play too. See you there!

Chisholm Trail Car & Motorcycle Show - Motors, Music & More!
2026-06-06 08:00 - 14:00 | Main Street Duncan, 828 W Main St B, Duncan, OK, 73533, United States
The annual Chisholm Trail Car Show is coming back in all its ‘ol Glory! This year the theme is “Thunder on the Trail” and you can look forward to all the cool cars, live music, great food, cold brews and more. New “Hometown Heroes” fun and demonstrations in the kid’s adventure section. Kid’s have their own car show, too!
$20 Registration begins at 8am and the show is 10am to 2pm. 30 awards, special prizes and lots to see and do 🙂
(Don’t miss the fun Poker Run the night before 6/5 registration begins at 5pm with great prizes and $10 hands.)
