Holiday Cheer in Milwaukee: Best Festive Events & Family Fun

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.

Oct

Milwaukee Holiday Shows 2025: Family-Friendly Performances for the Season

October 30, 2025mkewithkidsHoliday Cheer

How the Grinch Stole Christmas at the Marcus Performing Arts Center is a show for all ages. Experience the Magic of Milwaukee Holiday Shows in 2025! The holiday season is shining bright across Milwaukee, and the city’s stages are bringing the magic to life! From The Nutcracker and A Christmas Carol to dazzling productions like Cirque du Soleil’s ‘Twas the...

Oct

5 Best Milwaukee Christmas Markets for Families: 2025 Guide

October 28, 2025Calie HerbstHoliday Cheer

A mug of mulled wine at a Milwaukee Christmas Market Milwaukee’s Christmas Markets fill the air with the rich aroma of hot pretzels, grilled sausages, and cinnamon-roasted nuts. The sounds of polka music and festive chatter echo through the lively stalls, while twinkling lights and handcrafted treasures catch your eye at every turn. These family-friendly holiday markets create an immersive experience,...

Oct

Best Christmas Lights in Milwaukee (2025): Drive-Through, Walk-Through & Neighborhood Displays

October 28, 2025Calie HerbstHoliday Cheer

Updated for 2025 Children marvelling at one of the best Christmas drive-thrus in Milwaukee. Get ready to experience the best Christmas lights in Milwaukee for 2025! If you’re searching for the best holiday and Christmas lights near Milwaukee and southeastern Wisconsin, you’re in the right place. We’ve rounded up this year’s most magical light displays –...

Oct

Milwaukee Holiday Guide 2025: Best Christmas Lights, Santa Events & Festive Family Fun

October 27, 2025mkewithkidsHoliday Cheer

Santa & Mrs. Claus wave to the crowd during the Christmas Cavalcade in downtown Milwaukee. The holiday season is almost here, and Milwaukee is filled with festive things to do for families, from sparkling Christmas light displays and holiday markets to Santa sightings, winter shows, and beloved seasonal traditions. This guide brings everything into one place to make planning simple for busy parents. Each...

Oct

East Troy Christmas Train: What Families Can Expect (2025)

October 14, 2025Calie HerbstHoliday Cheer

The Christmas Train winds through a snowy winter landscape on its festive ride to Santa’s Workshop. If your family loves holiday traditions with a little bit of magic, the East Troy Christmas Train is one of the most memorable seasonal experiences in Southeast Wisconsin. This festive ride takes families on a charming journey to Santa’s Workshop at the...

LED Dancers at Chanukah Festival and Gelt Drop The Yard at Bayshore Whitefish Bay Wisconsin

Dec

Top Festive Chanukah Events Happening Around Milwaukee (2025)

December 9, 2024Calie HerbstHoliday Cheer

Each year the Hoan Bridge lights up like a giant menorah for Hanukkah on the Hoan. Chanukah is just around the corner, and there are some truly amazing events lined up this year. We’ve got the scoop on the top 5 you won’t want to miss. So grab your calendars and let’s dive in! Looking...

Dec

Where to See Reindeer in Milwaukee This Holiday Season (2025)

December 4, 2024Calie HerbstHoliday Cheer

The holiday season is the perfect time to experience the magic of live reindeer in Milwaukee with your family. All around the city and southeastern Wisconsin, you’ll find festive events where kids can meet reindeer up close and capture holiday memories. From tree lighting ceremonies to special holiday gatherings, here’s your guide to reindeer events near Milwaukee this December. 1....

Dec

5 Family-Friendly New Year’s Eve Events in Milwaukee (2025)

December 4, 2024Calie HerbstHoliday Cheer

Happy new year, Milwaukee! You may not be celebrating New Year’s Eve like you used to, but there are plenty of ways to ring in the new year with little kids. If you’re hunting for fun, family-friendly ways to celebrate New Year’s Eve without keeping the kids up past bedtime, you’re in luck! Milwaukee has...

Nov

‘Enchantment in the Park’ Brings One Million Lights to West Bend (2024)

November 21, 2024Calie HerbstFamily Fun Hub, Holiday Cheer

Washington County’s Enchantment in the Park returns to Regner Park in West Bend on Friday, Nov. 29, welcoming visitors nightly from 5 to 9 p.m. through Christmas Eve. Notably, on Dec. 1, the park will open at 6 p.m. following the West Bend Christmas Parade. On Dec. 8, the park will also open at 6 p.m. after...

Nov

Christmas-Themed Restaurants & Holiday Pop-ups in Milwaukee (2025 Guide)

November 14, 2024Calie HerbstHoliday Cheer

Santa Chalets at Natty Oaks in West Allis Milwaukee is full of cozy Christmas-themed restaurants, festive dining huts, and holiday pop-up experiences. If you’re looking for a spot that feels extra magical this time of year, this guide brings together the best places to eat, sip, and soak up the season. From heated chalets and...

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