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December 5, 2025
10:00am
December 7, 2025
3:00pm

Make your shopping experience extra special during Holly Jolly Days in Downtown Midland. On December 5-7, guests can find special holiday shopping deals, view beautifully-painted holiday window displays, cozy up by the outdoor fireplaces while enjoying a Commons beverage, and participate in family festivities.

Help us kick off Holly Jolly Days with our annual Jingle Bell Fun Run Walk on December 4 at 6:30 p.m. This fun, free 1-mile run or walk begins at 6:30 p.m. at the corner of Ashman and Main Streets in Downtown Midland. It’s not a timed race, so people of all ages are welcome to take their time and come dressed in their best festive gear (holiday sweaters, Santa hats, cool socks, etc.). All registered participants will receive a jingle bell bracelet to wear during the event. Furry friends and strollers are welcome – the more, the merrier!

Join Downtown Midland bars for our fourth annual Ugly Sweater Bar Crawl on Friday, December 5 starting at 7 p.m.!

Hours may vary as this event runs during the operating hours of each individual businesses.

Stay tuned for more details—we’ll be sharing more information soon, including a list of participating stores and exclusive offers.

  • Ace Hardware & Sports
  • Aviator Cookie Company
  • Bookmarks
  • Brinstar Arcade Bar & Grill
  • Coyer Candle Co.
  • FILL: Celebrate the season at FILL where you can find pre-made holiday gift bundles, sustainable stocking stuffers, and gift cards for easy gifting. Adults, make gift giving easy by taking advantage of their gift-wrapping station and while you are shopping your kids can send their letters at their North Pole station.
  • Health Hut: Stumped on stocking stuffers? Health Hut has you covered! Check out their seasonal Essential Oil blends, including, Candy Cane Lane, Sugar Plum, Woodland Walk and Pumpkin Spice. Also, don’t miss their NEW Lantern Style oil diffuser, with an electric faux flame and carrying handle.
  • Heather ‘n Holly
  • Joyful Tantrum: It’s stocking bar season at Joyful Tantrum! Fill a stocking for $5 off and grab a candy cane at checkout for a special gift or savings!
  • Little Forks Outfitters
  • Modern Explorers Guild
  • Molasses Smokehouse
  • Peel ‘n Pare
  • Pizza Baker
  • Pizza Sam’s
  • Proper Taco
  • Sassy & Chic Boutique: Discover new holiday merchandise at Sassy & Chic Boutique where the more you spend, the more you save! Spend $70 for 10% off, $100 for 15% off, or $150 for 20% off!
  • Serendipity Road: The Self-Care Bar — where shopping meets serenity. Stroll through their boutique filled with beautiful, soul-lifting finds, then try something just for you at their self care bar. Whether you’re crafting a candle, curating a bath ritual, or building your own self-care gift set, it’s all about embracing joy and don’t forget to pull a candy cane at checkout for a complimentary gift or discount.
  • Swae’ Spa
  • Tavern on Main
  • The H Hotel: Make your carriage ride even sweeter! Stop on by The H Hotel to purchase hot chocolate from their Beverage Cart under the clock tower during the following select times: Dec 5 (6–8 PM) and Dec 6–7 (12–3 PM)
  • Ways to Wellness: Get $5 off when you spend $40 or more!
  • WhichCraft Taproom