10/24/2026
Okay, okay... we know it's not even Halloween yet! BUT we're already looking ahead because Downtown Midland is about to get VERY festive! 🎄 🎁
❄️ November 6-7 | Holiday Open House | Hours vary by business
Step into the holiday spirit at Downtown Midland’s Holiday Open House on November 6–7! Shop local, discover holiday merchandise and special offerings, and stroll through downtown to see beautifully decorated wreaths created by participating businesses. Enter to win your favorite wreath, with winners announced at the end of the event!
☕ November 21 | Cocoa Crawl | 12:00 p.m. - 2:00 p.m.
Stick around Downtown Midland after the Santa Holiday Parade on November 21 for Cocoa Crawl from 12–2 p.m.! Visit participating downtown businesses to enjoy complimentary hot cocoa tastings, vote for your favorite, and help crown the winner of the Golden Mug Trophy. While you sip and stroll, browse local shops and add a few holiday finds to your Christmas wish list. Free for all ages while supplies last!
🏃 December 3 | Jingle Bell Fun Run | Run begins at 6:30 p.m.
Lace up and get festive for Downtown Midland’s Jingle Bell Fun Run on December 3! This free, untimed one-mile run or walk begins at 6:30 p.m. and welcomes all ages and abilities, with festive outfits, decorated furry friends, and strollers encouraged. More info to come soon!
🎅 December 4-6 | Holly Jolly Days | 10:00 a.m. - 7:00p.m. (5:00 p.m. on Sunday)
Get into the holiday spirit during Downtown Midland’s Holly Jolly Days, December 4–6! Shop local, discover special deals and holiday offerings, admire festive window displays, and enjoy family-friendly activities throughout downtown. The weekend kicks off with the Jingle Bell Fun Run/Walk on December 3, followed by the Ugly Sweater Bar Crawl on December 4 for a festive night out with friends.
🍻 December 4 | Ugly Sweater Bar Crawl | 7:00 p.m. - 11:59 p.m.
Downtown Midland is about to get ugly! Celebrate Holly Jolly Days and support your local bars and pubs during our third annual Ugly Sweater Bar Crawl. Starting at 6 p.m. on Friday, December 4, visit participating businesses and purchase specialty beverages all while in your ugliest Christmas gear! The event is free to attend and you must be 21+ to consume and purchase alcohol.
Save these dates NOW so you know where the fun is when the holiday season rolls around. But don't worry... Halloween can have its moment first! 😉
