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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.

Looking for a cozy winter adventure? Just a short drive from Milwaukee, you’ll find enchanting sleigh rides that are perfect for soaking up the holiday spirit. Picture snow-covered trails, twinkling lights, and the gentle jingle of sleigh bells as you’re pulled through scenic woodlands and festive farms. Bundle up, bring your loved ones, and get...
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One of Santa’s Mailboxes is in Cathedral Square Park in downtown Milwaukee. Santa Claus is making it easy for Milwaukee kids to send their holiday wishes straight to the North Pole! This season, you’ll find his bright red mailboxes popping up all around the city, ready to collect letters and wish lists. Gather your little...
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Bayshore recently announced its 3rd annual Season to Sparkle Holiday Celebration on Friday, November 22nd, 2024 from 5:00 – 7:00 p.m. in The Yard. The festivities will feature Kid Boogie Down, special visits with Santa, live reindeer with the Reindeer Games, Fairytale Princesses, new sparkling holiday decor including a giant illuminated walk-through ornament and 32′...
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Welcome to a special piece by Liz Brown, our talented Calendar Editor and a local parenting coach. In this insightful article, Liz blends her professional expertise and personal experience to guide parents through the delightful yet often tricky conversation about Santa. The most frequently asked question I get this time of year as a parent...
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