Downtown Midland plans full lineup of November events to celebrate the holiday season

Downtown Midland is getting ready to welcome the holidays with a full lineup of events throughout November. From the annual Holiday Open House and Santa Holiday Parade to the Cocoa Crawl and Small Business Saturday, there are plenty of reasons to shop, explore, and celebrate downtown.

Holiday Open House 

The season begins with Downtown Midland’s Holiday Open House on Friday, Nov. 7, and Saturday, Nov. 8. Shops and restaurants will feature new merchandise, holiday decor, seasonal menu items, and special services to help visitors get into the holiday spirit.

While strolling downtown, guests can enter to win beautifully decorated holiday wreaths designed by participating businesses. Winners will be announced at the end of the event.

Adding to the festive atmosphere, the Brush Monkeys will return for their seventh season, painting holiday scenes on shop windows throughout downtown. They’ll be at work all weekend, transforming storefronts into works of art that set the tone for the season. Hours vary by business.

Santa Holiday Parade

The holiday fun continues with the Midland Santa Holiday Parade on Saturday, Nov. 22, 2025. This year’s theme, “Sounds of the Season,” will bring music and holiday cheer to Main Street with floats, marching bands, and community groups celebrating the spirit of the season.

The parade marks the official start of the holidays downtown and leads right into the next event of the day — the Cocoa Crawl.

Cocoa Crawl 

After the parade, visitors can warm up with the Cocoa Crawl from 12 to 2 p.m. in Downtown Midland.

Hosted by the Midland Downtown Business Association, this free, family-friendly event features local retailers and restaurants serving up their own takes on classic hot cocoa. Participants can sample different recipes and then vote for their favorite between 12 and 2:15 p.m., either online or in person at Main and McDonald streets. The winning business will earn the Golden Mug Trophy and bragging rights for the season.

While sipping cocoa, guests can browse shops, grab lunch, and start checking off their holiday shopping lists. All Cocoa Crawl tastings are free while supplies last.

Small Business Saturday

Downtown Midland will wrap up the month with Small Business Saturday® on Nov. 29 from 8 a.m. to 4 p.m.

Shoppers can explore local stores and restaurants, take advantage of special deals, and enjoy a relaxed day of holiday shopping.

The day begins at Serendipity Road, 215 E. Main St., where a welcome station opens at 9 a.m. Visitors can pick up free shopping bags filled with goodies from downtown businesses, while supplies last. Boomerang Coffee will also be on site, serving complimentary coffee and hot cocoa to start the morning.

Small Business Saturday is a celebration of the people behind Midland’s local shops and restaurants, encouraging residents to support the businesses that make the community unique.

From painted windows and cocoa tastings to parades and local shopping, Downtown Midland’s November calendar is full of ways to celebrate the season. More details are available online.