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Holiday Cheer

Celebrate the most magical time of year in Milwaukee with our comprehensive guide to holiday events and activities. Discover where to see the best holiday lights, meet Santa, enjoy festive shows, and create unforgettable family memories throughout the season.

06
Nov

Milwaukee’s 10 Most Instagram-Worthy Holiday Photo Spots (2025)

November 6, 2025
Zeidler Union Square is home to larger-than-life photo opportunities for families. Milwaukee is bursting with festive locations perfect for capturing holiday memories. Whether you’re looking for twinkling lights, unique decorations, or cozy winter scenes, these Instagram-worthy spots are sure to delight. Looking for more holiday fun ideas? Be sure to check out our full Holiday...
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05
Nov

10 Magical Christmas Parades Around Milwaukee (2025)

November 5, 2025
Mrs. and Santa Claus are regular guests at Christmas Parades around Milwaukee. The holiday season is just around the corner, and for those in and around Milwaukee, it’s time to mark your calendars for the Milwaukee’s festive Christmas parades. Let’s explore some of the most exciting Christmas parades in the Milwaukee area, each offering unique...
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05
Nov

Where to Find Black Santa Experiences in Milwaukee (2025)

November 5, 2025
The holiday season is a time for joy, celebration, and creating cherished memories—and representation matters. For families seeking to celebrate with a Black Santa, Milwaukee offers several wonderful opportunities to connect with Santas who reflect the diversity of the community. From in-person appearances to virtual visits, these events bring holiday magic to children and families...
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Cocoa With the Clauses Cathedral Square Park Milwaukee Wisconsin
04
Nov

Free Holiday Events in Milwaukee (2025): 30+ Family Picks

November 4, 2025
Downtown Milwaukee shines during the annual Holiday Lights Festival Looking for free holiday events in Milwaukee? You’re in luck – the city shines extra bright this time of year! From twinkling light displays and cozy cocoa moments to festive parades and Santa sightings, there are countless ways to celebrate without spending a dime. Here’s your ultimate...
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04
Nov

Lake Geneva Santa Cruise: A Festive Holiday Boat Ride for Families

November 4, 2025
The combination of holiday lights, Santa’s appearance, and boat tour turns the Lake Geneva Santa Cruise into a unique holiday experience. The Lake Geneva Santa Cruise is one of the most magical winter experiences for families in southeastern Wisconsin. Each holiday season, Lake Geneva Cruise Line transforms its historic boats into cozy, festive vessels that...
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04
Nov

Magical Holiday Experiences Near Milwaukee (2025): Storybook Adventures for Families

November 4, 2025
One of the many magical holiday experiences families can enjoy around Milwaukee. Get ready, Milwaukee – this holiday season is packed with unforgettable moments that feel straight out of a storybook. These aren’t your everyday light displays or Santa photo ops, they’re experiences that immerse your family in the magic of the season. Step aboard festive trains,...
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02
Nov

5 Sweetest Gingerbread Displays for Families Around Milwaukee in 2025

November 2, 2025
Updated for 2025 The Milwaukee Public Market hosts the area’s most popular gingerbread house contest each year. Looking for the best gingerbread houses and displays near Milwaukee this holiday season? From the Milwaukee Public Market to cozy spots like North Shore Boulangerie, these festive gingerbread creations are some of the most beloved holiday activities for families in southeastern Wisconsin. Here’s where to...
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02
Nov

Milwaukee Holiday Lights Festival 2025: 15 Must-See Events & Displays Downtown

November 2, 2025
Kids and adults look forward to the beloved Milwaukee Holiday Lights Festival every year. Get ready to be dazzled as the Milwaukee Holiday Lights Festival returns for its 27th season! From November 20, 2025, to January 1, 2026, downtown Milwaukee will come alive with holiday magic, featuring over half a million lights, animated sculptures, and...
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01
Nov

10 Breakfast With Santa Events Happening Around Milwaukee This Year (2025)

November 1, 2025
Santa shares his laughter and festive cheer at one of the Breakfast with Santa events around Milwaukee. Looking for a magical way to celebrate the season with your loved ones? Discover the joy of breakfast with Santa in Milwaukee! This cherished holiday experience offers families a chance to enjoy delicious meals, festive activities, and cherished...
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01
Nov

5 Best Places to See Holiday Trains Around Milwaukee (2025)

November 1, 2025
Kids always look forward to the festive holiday trains around Milwaukee. The holidays are here, and there’s something undeniably magical about holiday trains. Whether it’s a brightly lit locomotive rolling into town or a miniature model train weaving through a festive display, trains are a timeless symbol of holiday cheer. From live performances on real...
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