Pictures with Santa
Westport Plaza—Capture the magic of the holidays with Pictures with Santa at Westport Plaza, where you can enjoy photos on Santa’s sleigh. December 6, 13, and 20th from 10:00am-12:00pm. Enjoy the sounds of the season with holiday music and special activities. Bring your family to Westport Plaza and create cherished memories filled with holiday cheer.
Ugly Sweater Skate
December 19th, Centene Community Ice Center—Don your best ugly sweater for the Ugly Sweater Skate Friday, December 19 from 7:30-9:30pm! Sleigh National Ugly Sweater Day and fill the rink with the loudest holiday looks around! Sip into the holiday spirits with hot cocoa (boozy or not) and enjoy $2 off bottled beer and $5 well cocktails when you wear your ugly sweater. Grab your ugly sweater and pre-register for easy check-in for the 12/19 7:30pm public skate today!
Pop, Fizz, Clink: The Ultimate NYE Party
December 31st, 360 Westport—Ready to ring in 2026 with a BANG?! Don’t miss a night of glamour, excitement, and endless fun at this all-inclusive NYE bash. Open bar with all your favorite drinks, full buffet with high-end hors d'oeuvres and carving stations - available from 9-11pm, DJ Rops & Charles spinning the hottest hits and firework show & champagne toast to ring in the New Year at midnight! Tickets: $185 (all-inclusive). Don't miss your chance to countdown in style with an unforgettable night of delicious drinks, food, and the best NYE vibes.
Scott James
December 26-28th, Funny Bone Westport—Hailing from St. Louis, Missouri, Scott James weaves jokes and stories together for the comedic effect you’d expect around a bar table or construction site. His take on marriage, divorce, fatherhood and maturity swing wildly from the practical to the absurd to the delight of audiences in the St. Louis area and beyond.