What an unforgettable night! On December 6, 2024, the Monument Square District transformed The Cheetah Lounge into a dazzling 1920s-style wonderland for the Father Christmas Speakeasy – Spirits & Games of Chance. From the moment the doors opened, guests stepped into an era of glitz and glamour, surrounded by holiday cheer and the warm spirit of our amazing community.

From stunning Roaring Twenties attire to thrilling games of chance, the evening was packed with festive fun. Guests enjoyed delicious food, bid on exciting auction items, and laughed the night away, all while supporting local initiatives that keep Urbana thriving.

The atmosphere was made even more magical thanks to the nostalgic holiday music, creative costumes (congratulations to our Best Dressed winners!), and, of course, the fantastic energy of everyone who attended.

We owe a huge thank-you to everyone who made this night possible—our dedicated volunteers, generous sponsors, and most of all, the incredible community members who joined us. Your support makes events like this possible and helps ensure that Monument Square District continues to flourish.

Ready to relive the fun? Check out the photo slideshow below by the talented Andy Grimm. We hope these memories inspire you to mark your calendars for next year’s holiday festivities—trust us, you won’t want to miss out!

​Thank you for making this night so special, and we can’t wait to celebrate with you again soon.

Monument Square District is inviting all downtown businesses to bring some extra holiday cheer with this year’s "Winter Wonderland" Window Decorating Contest. Set to transform the heart of downtown into a festive wonderland, the contest aims to attract holiday shoppers and visitors with beautifully decorated storefronts.

How to Enter: All businesses and merchants in the downtown area are automatically entered, so every business is encouraged to join in the fun and decorate their windows by the night of the annual parade on November 29th. To boost the holiday spirit, windows are encouraged to feature nighttime lighting, adding a magical glow to the streets after dark.

Judging Criteria and Prizes: Judges will assess the window displays from November 29th to December 1st, looking for creativity, curb appeal, attention to detail, and how well they incorporate the "Winter Wonderland" theme. The top three winners will each receive a monetary donation to a charity of their choice, along with a certificate and the opportunity to be highlighted on Monument Square District's social media platforms.

Winners will be announced on December 4th.
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This contest promises to make the downtown shopping experience even more special for the community and visitors alike. Monument Square District hopes everyone will come downtown to enjoy the holiday displays and support local businesses.

The ​Monument Square District would like to thank all of the merchants/business and voters that helped to make the Flannel & Fall Window Contest a success as a new event. After 328 votes, we would like to congratulate the winner, Downtown Divas! 

The following is a list of the Top 8:
Downtown Divas
Tommy Brooks Salon
Dee Brew Coffee
Our Kitchen Window Winery & Home Goods
Vintage Traveler
Guild Gallery Interior
Ethel’s Flower Shop
The Peoples Savings Bank

Thank you to all merchants/businesses and thanks again to Andy Grimm for the photography!