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.

Dec

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

December 4, 2025Calie 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...

Dec

100 Fun Christmas Trivia Questions for Kids (With Answers) – 2025

December 1, 2025Calie HerbstHoliday Cheer, Trivia & Questions

Looking for fun, kid-friendly Christmas trivia questions with answers? This list of 100 Christmas trivia questions for kids is perfect for classroom games, holiday parties, family movie nights, and quick brain breaks in December. Questions are organized by theme and written for elementary-age kids, with clear answers included so you can start playing right away. Looking for even more kid-friendly...

Nov

The Miller Valley Holiday Lites Are Back: What Families Need to Know (2025)

November 25, 2025Calie HerbstHoliday Cheer

One of Milwaukee’s beloved holiday traditions, the Miller Valley Holiday Lites, is returning this winter. This drive-thru display offers families a magical way to soak in the festive spirit without leaving the warmth of their car. Here’s everything you need to know to plan your visit: Looking for more festive fun? Check out our Best Holiday Light Displays in Milwaukee for a complete...

Nov

Enchantment in the Park: West Bend’s One-Million-Light Holiday Display

November 21, 2025Calie HerbstHoliday Cheer

A stunning view of Enchantment in the Park, with colorful lights reflecting beautifully across the lake. Updated for 2025 — Dates Below If you’re mapping out festive stops this season, Enchantment in the Park is one of the easiest and most family-friendly holiday light displays to add to your list. It’s an annual favorite for...

Nov

Holidays on The Hop (2025): Live Music, Free Cookies & Festive Fun on Milwaukee’s Streetcar

November 21, 2025Calie HerbstHoliday Cheer

Families board The Hop during Milwaukee’s festive holiday streetcar celebration. Quick Overview: Holidays on The Hop returns December 7, 14, and 21, 2025 with live holiday music on board The Hop, free cookies, and festive vibes along the Milwaukee streetcar route. All performances run 4–6 p.m. and are free to ride. Milwaukee’s streetcar is getting...

Nov

World’s Tallest Glass Tree: A Family Guide to the Yerkes Observatory Holiday Experience

November 18, 2025Calie HerbstHoliday Cheer

Families gather at Yerkes Observatory to see the unveiling of the world’s tallest glass tree, a stunning holiday installation that draws visitors from across Wisconsin. For a holiday tradition that is as unique as it is awe-inspiring, make plans to visit the World’s Tallest Glass Tree at Yerkes Observatory in Williams Bay, Wisconsin. This one-of-a-kind art installation...

Nov

Milwaukee County Zoo’s Wild Lights 2025: What Families Can Expect This Holiday Season

November 18, 2025Calie HerbstHoliday Cheer, Zoos & Aquariums

Elephant and giraffe light displays at the Milwaukee County Zoo Wild Lights 2025 The zoo is lighting up even earlier this year! Wild Lights, presented by the We Energies Foundation, returns with 28 dazzling nights of holiday magic — now with an expanded route, more displays, and fun new themed evenings for families (and even dogs!). Running on...

Nov

Things to Do with Family on Thanksgiving Weekend in Milwaukee (2025)

November 17, 2025Calie HerbstHoliday Cheer

The Ornament Trail features larger-than-life, hand-painted ornaments placed along Wisconsin Avenue in Downtown Milwaukee. Looking for family-friendly events and activities over Thanksgiving weekend in Milwaukee? Whether you’re hosting relatives, visiting town, or just hoping to keep the kids entertained, there’s plenty happening from Friday through Sunday to kick off the holiday season. From festive tree lightings...

Nov

Holidays at The Domes 2025: What Families Need to Know

November 12, 2025Calie HerbstHoliday Cheer

The holiday theme for the 2025 Holiday at the Domes is “The Twelve Days of Christmas: A Playful Parody. The holidays are a magical time to visit The Domes (524 S Layton Blvd, Milwaukee, WI 53215), where the warm, indoor gardens transform into festive wonderlands for families to discover together. From late-night explorations to concerts...

Nov

Milwaukee Christmas Tree Farms (2025): 10 Best Places to Cut or Choose Your Tree

November 10, 2025mkewithkidsHoliday Cheer

Visiting the best Christmas tree farms around Milwaukee with family adds a memorable experience rather than just buying a tree off a lot. Looking for the perfect Christmas tree near Milwaukee? These family-owned Christmas tree farms in the Milwaukee area are open for business in 2025, offering fresh-cut and choose-and-cut options, festive activities, and holiday...

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