Shop, Dine & Delight: Winter Events in Downtown Midland
SHOP, DINE, DELIGHT DOWNTOWN MIDLAND’S WINTER WONDERLAND
Downtown Midland is the destination of the season! Stroll streets aglow with lights, explore unique shops, savor seasonal bites, and soak up the magic of the holidays — all while supporting local businesses.
Whether you’re looking for festive fun, holiday shopping, or cozy dining, Downtown Midland has something for everyone.
Check out our lineup of holiday events below and make this season unforgettable!
Holiday Open House – Nov. 7-8
Celebrate the season at Downtown Midland’s Holiday Open House on November 7–8! Explore festive merchandise, holiday treats, and special offers, enter to win decorated wreaths from local shops, and catch the Brush Monkeys painting cheerful holiday scenes on downtown windows November 3–7.
Cocoa Crawl – Nov. 22
After the Midland Santa Holiday Parade on November 22, stick around Downtown Midland from 12–2 p.m. for the Cocoa Crawl! Sample hot cocoa from local shops and restaurants, vote for your favorite to win the Golden Mug Trophy, and enjoy a cozy afternoon of sipping, shopping, and holiday fun.
Jingle Bell Fun Run – Dec. 4
Join the festive fun at the Jingle Bell Fun Run on December 4! This free, 1-mile family-friendly run/walk starts at 6:30 p.m. and welcomes all ages, pets, and strollers. Dress in your best holiday gear and receive a jingle bell bracelet (while supplies last). Instead of a fee, bring nonperishable food donations for the Midland County Food Assistance Network to support local families.
Ugly Sweater Bar Crawl – Dec. 5
Starting at 7pm: Downtown Midland is about to get ugly! Celebrate Holly Jolly Days and support your local bars and pubs all while in your ugliest Christmas gear! The event is free to attend and you must be 21+ to consume and purchase alcohol.
Holly Jolly Days – Dec. 5-7
Make your shopping experience extra special at our Holly Jolly Days where shoppers can find special holiday shopping deals, view beautifully-painted holiday window displays, and free horse-drawn carriage rides.
Holiday Rush – Dec. 19
Finish your holiday shopping in style at Downtown Midland’s Holiday Rush on December 19! Whether you’re a planner or a last-minute shopper, participating businesses will offer special deals and gift stations to help you wrap up your list. Plus, shoppers that day can enter to win a festive stocking filled with goodies from downtown businesses!
ADDITIONAL FESTIVE EVENTS DOWNTOWN
LEARN MORE BY CLICKING THE NAME OF THE EVENT BELOW
Santa Parade – November 22
The Midland Santa Holiday Parade is a non-profit organization run by a small, dedicated group of volunteers. The sole purpose of the Midland Santa Holiday Parade is to run a holiday parade while providing The Salvation Army’s local Toys for Kids program with some much needed funding. This year’s theme is “Sounds of the Season”. Learn more at midlandsantaparade.org
Black Friday at Serendipity Road – November 28 from 8 a.m. – 12 p.m
Black Friday at Serendipity Road isn’t just about shopping — it’s about choosing joy, choosing local, and choosing to bless the place we call home. This year, the earlier you shop, the more you save — and every purchase helps fuel creativity, community events, and the small makers and dreamers we love supporting.
From thoughtful hostess gifts and handmade treasures to cozy winter favorites, your dollars stay right here in Midland — doing good, spreading kindness, and keeping our small-town magic alive. Come shop early. Leave inspired. Find a little serendipity. Feel joy. Learn more at facebook.com/SerendipityRoadMI
Small Business Saturday – November 29
Shop Downtown Midland on November 29 for Small Business Saturday®. Serendipity Road join forces with other small businesses to bring you the best shopping experience in Downtown Midland.
Start your shopping adventure at the Downtown Midland Welcome Station at Serendipity Road where you can warm up at the Coffee + Hot Cocoa Bar and grab a complimentary shopping bag filled with gifts from local downtown shops (while supplies last!).
Then, sip, stroll, and shop your way through your favorite Midland boutiques, shops, restaurants and bars. Every purchase keeps our small-town spirit thriving — and your day a little more joy-filled. Learn more at downtownmidland.com or Facebook.
Poseyville Preserve Ribbon Cutting – December 2 at 4:30 p.m.
Santa is coming to Midland early this year to celebrate the grand opening of the Poseyville Preserve, home of Founders Crossing and the Alan W. Ott Family Pavilion! The ribbon cutting will take place on December 2 at 4:30 p.m. at East Main Street near the East End Building. Enjoy free cocoa, cookies, and goody bags for children as we celebrate this exciting new community space. Learn more at cityofmidlandmi.gov/poseyville
Downtown Midland Holiday Tree Lighting – December 2 at 5:30 p.m.
On your way from the Poseyville Preserve Ribbon Cutting to the courthouse to watch Santa’s arrival, be sure to stop by Downtown Midland’s new holiday tree for its lighting! This is the newest holiday decoration purchased by the Downtown Development Authority.
The tree is located at the corner of Cronkright and Main Street, across from Ace Hardware.
A special thank-you to Three Rivers Corporation for helping us install our tree!
Kid’s Shopping Event at Serendipity Road – December 2 & December 16 from 5-7 p.m.
The best gifts come from the heart — and the smallest shoppers! Bring your little gift-givers for an evening filled with thoughtfulness, independence, and holiday magic. Whether they’re shopping for parents, siblings, teachers, grandparents, or friends, this night is all about empowering kids to give from the heart. Make it a family outing, grab a hot cocoa downtown, and let your little shoppers create some joyful holiday memories. Learn more at facebook.com/SerendipityRoadMI
Santa Arrival & Courthouse Lighting – December 2 at 6 p.m.
It’s a magical evening each year when the lights go on in front of Midland’s courthouse and, for many children and adults, the holidays begin! Every year the courthouse lighting heralds Santa’s arrival and the opening of his house for visitors young and old alike.
Santa will be making his way over the Tridge at 6:30 PM on December 3. Following Santa’s arrival will be the Courthouse and Santa House lighting. This is a Midland Area Community Foundation event you can learn more at midlandfoundation.org/santahouse or on Facebook
The Santa House & Northern Star Train – December 2 – 23
The Santa House, located at the corner of M-20 and Main Street, is a holiday staple in the Midland community. The house is located next to the Midland County Courthouse (301 W Main St, Midland, MI 48640). The present house was built in 1987 with assistance from the Midland Area Community Foundation and generous donors. It continues to operate annually, thanks to the donation of time from volunteers and to endowed funds held at the Community Foundation that support the yearly operation of the house. Learn more and view the schedule at midlandfoundation.org/santahouse or on Facebook
