Shorewood Winterfest

Bring your family to Shorewood's annual holiday celebration, where the village transforms into a winter wonderland of festive activities. A vintage sleigh carries Santa to multiple stops throughout the neighborhood, giving kids a chance to meet him in person at locations like Blackbear Children's Boutique, Scout Wine Merchants & Stone House Collective, Draft & Vessel, and Wood Square. Along the way, you'll find cookie decorating, holiday lights, and special food and drink offerings at local businesses. Don't forget to have your children write letters to Santa—mailboxes are available outside Foxhole Craft Beer Shop & Kitchen. The evening culminates at Wood Square with a tree and Menorah lighting ceremony, plus additional festivities at Camp Bar Shorewood. This year's celebration also includes a special ribbon-cutting to mark the reopening of Oakland Avenue following a major reconstruction project. It's a wonderful way for families to explore the community while enjoying seasonal traditions together in one convenient, walkable area.