Artistic rendering – Event may differ
Holly Jolly Days
Experience the festive spirit of Holly Jolly Days in Downtown Midland from December 5-7, 2025. This event transforms the downtown area into a winter wonderland with special holiday shopping deals, charming window displays, and cozy outdoor fireplaces. Participate in the free Jingle Bell Fun Run Walk or join the lively Ugly Sweater Bar Crawl. Discover unique gifts and seasonal treats from a variety of local shops and businesses.
What to Expect
Holiday shopping deals and festive window displays
Know Before You Go
- Tickets: $$
- Pets: Pet-friendly for Jingle Bell Fun Run Walk
Other Christmas Events Near Midland
Local Insight & Ratings
Family Friendly
Best For
Holiday shopping and festive activities
Vibe
Festive and community-oriented
Energy Level
Moderate
Budget
$$
Photo Friendly
Weather Sensitivity
Low
Special Events & Promotions
- Special holiday shopping deals
- Beautifully-painted holiday window displays
- Outdoor fireplaces with beverages
- Jingle Bell Fun Run Walk (free)
- Ugly Sweater Bar Crawl
- Gift-wrapping station at FILL
- North Pole station for letters at FILL
- Seasonal Essential Oil blends at Health Hut
- Lantern Style oil diffuser at Health Hut
- Stocking bar season at Joyful Tantrum
- Self-Care Bar at Serendipity Road
- Hot chocolate at The H Hotel
- Discounts at Sassy & Chic Boutique
- Discounts at Ways to Wellness
Location
Event Details
Duration
10:00am - 11:00pm daily
Ages
All ages
Neighborhood
Downtown Midland
Timed Entry
No
Organizer
Downtown Midland
Food & Drink
Food trucks and beverage vendors available, hot chocolate at The H Hotel
Quick Actions
Tips & Advice
- Arrive early on Friday to take advantage of the best shopping deals and explore the window displays before the evening crowds.
- Dress in festive attire for the Jingle Bell Fun Run Walk on December 4th to fully embrace the holiday spirit.
- Check the individual business pages on the Downtown Midland website for specific offers and hours during Holly Jolly Days.
- Consider visiting on Thursday evening for the Jingle Bell Fun Run Walk and then returning Friday or Saturday for the main shopping event.
- Bring a reusable bag for your purchases to make shopping more convenient and eco-friendly.
Frequently Asked Questions
What are the main dates for Holly Jolly Days?
Holly Jolly Days officially runs from December 5-7, 2025, with the Jingle Bell Fun Run Walk taking place on December 4, 2025.
Are there any special activities for children?
Yes, the Jingle Bell Fun Run Walk is family-friendly, and the FILL store offers a North Pole station for kids to send letters.
What kind of shopping deals can I expect?
Participating businesses will offer special holiday shopping deals, discounts, and gift-wrapping services. Specific offers will be announced closer to the event.
Is there food and drink available?
Yes, you can enjoy beverages from The Commons and purchase hot chocolate at The H Hotel during select times. Food trucks and vendors will also be present.
What is the Ugly Sweater Bar Crawl?
The Ugly Sweater Bar Crawl is a fun event on Friday, December 5th, starting at 7 PM, where participants wear their ugliest holiday sweaters while visiting various downtown bars.
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.