Each year since our founding, Christmas in Crestwood volunteers strive to provide opportunities for children, families, and adults to join the fun and enjoy our community while discovering Crestwood businesses and all our community has to offer.

Crestwood was established as a Village on November 12, 1947. The spirit of Crestwood is an endorsement of the City’s rich history beyond its Sappington, Long, Eddie, and Park heritage. Crestwood, its businesses, and its residents continue to proudly build a community of strong neighbors, memorable programs, and dynamic firsts at the City, County, Region, and State levels. Time and again Crestwood has proven itself a gem in the St. Louis region, earning a special place in the hearts of anyone who find themselves within its boundaries.

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2025 planning is underway! Check back for more details.

TRIVIA NIGHT FUND RAISER — November 14

SANTA IS COMING TO CRESTWOOD — December 6
includes Santa Car Cruise, goody bags, kid’s workshop, pictures with Santa, face painting, balloons artists, and more

Let’s Light Up Crestwood with Color and Cheer: We are not having organized decorating contests this year, but we encourage everyone — businesses and residents — to decorate and light up Crestwood with joy and friendship this holiday season.

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November 14th - 3rd Annual Trivia Night Fund Raiser

An evening of general trivia and a lot of fun! Join in the fun as we raise funds to support Christmas in Crestwood’s Big Celebration on December 6, as well as programs and events planned for 2026!

• Silent Auction and 50/50 Raffle
• Attendance Prizes
• Featuring St. Louis Classic Rock’s game “Six Buckets of Fun”
• Location: Woodard, 9490 Watson Road
• Trivia starts at 7:00 p.m., door open at 6:00 p.m.
• $200 per table of eight
• 15 mulligans for $20
• 1st Prize: $250 | 2nd Prize: $125
• Soda, water, beer, and light snacks provided

REGISTER ONLINE @ www.StLouisTrivia.com

December 6th - Santa is Coming to Crestwood!

An afternoon and evening of holiday fun and giving!

• WINTER WONDERLAND and KIDS’ WORKSHOP. Brought to you in part by the generous Crestwood Business Community, the magic includes fun activities for kids, face painting, clowns, goody bags, raffles, treats, and snapshots with Santa! Join us at the Crestwood Community Center in Whitecliff Park. Time TBD.


• GOODY BAG FOOD DRIVE. Trade five (or more) non-perishable food items for one children’s goody bag filled with kid-friendly trinkets, simple non-perishable treats, small toys, and more — donated from businesses throughout Crestwood! Available to the first 200 donators. Collected food is donated to the First Baptist Church of Crestwood’s food pantry. (no glass containers please; goody bags exchanged on a first-come basis)


• SANTA CAR CRUISE through Crestwood. Our car cruise will include a myriad of decked out vehicles escorting Santa throughout Crestwood. Time and route TBD. Interested in being in the car cruise? Car Cruise registration coming soon. (Single vehicles, no trailers, decorations encouraged.)

Click here (or follow the link in the right-hand navigation) for more December 6th details.

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Shop Crestwood for the Holidays!

We continue to thank our Christmas in Crestwood sponsors and supporters. In our Shopping Guide, we highlight gift ideas and specials from our wonderful Crestwood businesses. These great gift ideas help you shop local and keep your gift-giving creative (they will never guess what they are going to get). Shopping in Crestwood supports our local businesses, which supports our community, which keeps our taxes from rising — win, win, win.

Click here (or follow the link in the right-hand navigation) for more Shopping Guide details.