Shorewood Winterfest 2025: Tree & Menorah Lighting
Bundle up and mark your calendars for one of Shorewood’s merriest traditions—Winterfest at Wood Square! On Saturday, December 6th, 2025, families are invited to join a free celebration full of holiday cheer, community fun, and dazzling lights from 3:30pm to 6:30pm, capped by the Tree & Menorah Lighting at 5:45pm.
Discover the Magic of Shorewood’s Winterfest
Winterfest offers a joyful stroll through Shorewood, with festive stops, treats, and plenty of chances to meet Santa himself! Gather your loved ones and visit these Santa Stops, where our vintage sleigh brings Santa to each location:
3:30pm – Blackbear Children’s Boutique
Enjoy craft time beginning at 3pm, plus milk & cookies as you await Santa’s arrival at 3:30pm.4:15pm – Scout Wine Merchants & Stone House Collective
Sip complimentary bubbles at Scout Wine Merchants and warm up with hot chocolate at Stone House Collective while Santa visits.5:00pm – Draft & Vessel
Sit by the cozy fire and grab a free hot chocolate or mulled wine as you wait for Santa’s next appearance.5:45pm – Wood Square
The celebration reaches its peak with the Tree & Menorah Lighting!Performances by Milwaukee Irish Dance Studio add festive flair.
Cookie decorating near the tree is sponsored by Metro Market Shorewood and Little Sprouts Play Cafe.
6:15pm – Camp Bar Shorewood
Close out the evening with family fun and one last visit from Santa!
Special Activities and Local Cheer
Keep the holiday spirit alive by writing letters to Santa, courtesy of Allstate – Andrew McCabe Agency (mailbox located outside Foxhole Craft Beer Shop & Kitchen). Don’t miss amazing deals, giveaways, and exclusive treats at every Santa Stop!
Family-friendly specials include:
Craft time and cookies at Blackbear Children’s Boutique
Complimentary wines and hot chocolate at Scout Wine Merchants and Stone House Collective
Free hot chocolate and mulled wine at Draft & Vessel
Delicious cookie decorating at Wood Square
Enchanting Irish Dance performance
Bring the Whole Family—Celebrate Together
Join your neighbors in Shorewood to kick off the holiday season. Winterfest is a heartwarming way for families to come together for an evening of laughter, music, delicious treats, and the glow of beautiful lights. It’s a can’t-miss event that brings generations together for lasting memories.
Let the festivities begin!
The Steamer Appomattox—once the world's largest wooden bulk carrier at 319 feet long—offers families an incredibly rare opportunity: a National Register shipwreck so shallow and accessible that kids can actually see it from the surface.