HOLIDAY OPEN HOUSE
Santa, holiday decor, lights, cookies, shopping, and fun! The Annual Holiday Open House with downtown Madison shops is always a crowd favorite. Join us on November 13th and 14th, 2026!
EVENT INFORMATION
SAVE THE DATES: NOVEMBER 13-14, 2026
Gather your friends and family for a magical evening in downtown Madison as we kick off the holiday season together!
When you make a purchase at any participating store and fill out a "Letter to Santa," you’ll be entered into our drawing for a chance to win a $100 gift card to that store! We’ll be drawing 5 lucky winners, totaling $500 in downtown shopping sprees!
Each year, you'll be able to purchase a limited-edition Collectible Cookie Tins featuring a unique Madison design by a local artist, exclusive to this event!
Each tin comes with delicious cookies from a local business. When you purchase your tin, pick it up at the Main Street office, then collect your cookies from 10 different downtown locations.
STAY TUNED FOR
LETTER TO SANTA PARTICIPATING BUSINESSES
Closer to the event, we will list the Downtown Madison businesses that will participate in the 2026 Letter to Santa! After making a purchase at any of the participating stores during Holiday Open House, customers fill out a Letter to Santa sheet and be entered in to win a gift card back to that business!
STAY TUNED FOR
2026 COOKIE STOPS
If you purchase a Collectible Cookie Tin, the businesses that will be listed below closer to the event will be where you’ll pick up your cookies! you'll bring your cookie stop card to each location, and they’ll mark it off when you receive your cookie!
STAY TUNED FOR THE
MADISON TROLLEY LINE ROUTE
CARD BUNDLES FOR SALE (YEAR ROUND!)
We’re excited to share that this year’s Holiday Open House design by local artist Eric Phagan is now available as a bundle of 5 blank cards, perfect for any occasion! Each bundle is just $20, and with only a few bundles still available, they won’t last long. Proceeds support the Madison Main Street Program, so your purchase gives back to our mission!
THANK YOU
2026 Event Sponsor!
EVENT FAQ
