What to Expect This Christmas in Wauwatosa!
Can't wait for the holiday joy in Wauwatosa? Dive into our guide for the best festive events! For Wauwatosa connoisseurs and newcomers, our guide is the recipe for holiday delight. Popular events during the season include the Wauwatosa Holiday Market, where local artisans and vendors showcase unique gifts and treats that capture the spirit of the holidays. Featuring breathtaking music and stunning visuals, the Trans-Siberian Orchestra delivers a dynamic concert experience that is sure to resonate with audiences of all ages. And the beloved classic, The Nutcracker, is something you definitely don't want to miss as it brings the enchanting tale to life on stage. See more details on these and other fun events and activities below!
Find the best Christmas events in Wauwatosa this year!
Wauwatosa Christmas Events
Wauwatosa Christmas Markets and Shopping (2)
When
Wednesday, December 3, 2025
Event Details
Event Description
Join the festive kickoff to the holiday season in Wauwatosa Village! The evening begins with warm drinks and a special performance by local students, culminating in the magical lighting of the Village tree. Afterward, Santa arrives for photos, followed by the grand opening of the Wauwatosa Holiday Market with a ceremonial keg tapping.
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When
Thursday, November 20, 2025
Event Details
Event Description
Discover the enchanting 'Holidays In the Village' event series, transforming Wauwatosa into a festive wonderland. This celebration features a Holiday Sip & Stroll, encouraging exploration of local shops and dining. Small Business Saturday offers a prime opportunity to support local artisans and find unique gifts. While specific dates for the CP Holiday Train stop, Wauwatosa Holiday Market, and Village Tree Lighting are TBD, the season promises a magical experience.
MoreWauwatosa Christmas Food, Drink and Parties (1)
When
Thursday, November 20, 2025
Event Details
Event Description
Experience the magic of the holiday season at the Wauwatosa Holiday Sip & Strolls. This festive event invites you to wander through the charming, historic Village of Wauwatosa, adorned with twinkling lights and holiday cheer. Local shops and restaurants offer delightful sips, treats, and special promotions, creating a perfect evening to celebrate with friends and discover unique finds.
MoreWauwatosa Other Christmas Activities (1)
When
Saturday, December 6, 2025
Event Details
Event Description
Get ready for the Santa Cycle Rampage, a joyous holiday bicycle event rolling through Milwaukee on December 6th, 2025, and Madison on December 13th, 2025. Participants are encouraged to don festive holiday costumes for a memorable ride that supports youth and family education programs in Dane and Milwaukee Counties. Registration details, routes, and sponsor information will be released on October 1st.
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