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, hot cocoa, and festive holiday music. December 6, 13, and 20 from 6:00pm-8:00pm or December 7, 14, and 21 from 10:00am -12:00pm. On December 14, 20, & 21, the fun gets even bigger with balloon twisters and face painters. Bring your family to Westport Plaza and create cherished memories filled with holiday cheer.
Christmas with C.S Lewis
Westport Playhouse—The Westport Playhouse presents the acclaimed one-man play “Christmas with C.S. Lewis” on the intimate Playhouse stage Nov 29-Dec 15. Join C.S. Lewis at his home near Oxford on Christmas Eve hosting a group of Americans who are Christmassing in England. They are about to experience an unforgettable assortment of Yuletide recollections which stimulates a whole range of emotions – curiosity, laughter, gladness and even some tears.
Holiday Skate - AFTER HOURS
December 20–21st, Centene Community Ice Center—"Start lining up a sitter because the adults-only holiday event of the season is back! Holiday Skate: AFTER HOURS presented by NÜTRL will feature ice skating, a live DJ, boozy hot chocolate bar, yard games, fire pit, and more. Find a sitter and get the squad ready for a fun, kid-free, holiday evening on the ice! Skater $20 - includes admission, skate rental, and one drink ticket. Non-skater $15 - includes admission and one drink ticket, no skating.
Pop, Fizz, Clink: The Ultimate NYE Party at 360 Westport!
December 31st, 360 Westport—Ready to ring in 2025 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 Rico Steez spinning the hottest hits and firework show & champagne toast to ring in the New Year at midnight! Tickets: $175 (all-inclusive). Don't miss your chance to countdown in style with an unforgettable night of delicious drinks, food, and the best NYE vibes.