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 section includes dates, locations, and insider tips so you can easily choose what works for your family.
Bundle up, pick your favorites, and enjoy a season full of joy, wonder, and memory-making in Milwaukee and southeastern Wisconsin. Happy holidays!
What’s NEW in 2025?
The 2025 holiday season bring plenty of new magic for families:
- Holiday Window Display at Milwaukee Public Market — Ten student-designed installations transform St. Paul Avenue into a festive outdoor gallery (on display through Jan. 31).
- Winter Glow at Brown Deer Park debuts as a dazzling drive-through light show set to music
- Christmas Carnival of Lights adds a snowless tube slide, skating, and a glowing walking path.
- Friday Night Holiday Lights at the Villa debuts for two nights only (Dec. 5 & 12)
- Breakfast with Santa at Old World Wisconsin is back after a 10-year hiatus.
- Families can also catch festive shows like How the Grinch Stole Christmas and The Pigeon Gets a Big Time Holiday Extravaganza
- Enjoy holiday films at the new Argo in Whitefish Bay
- While the Tosa Holiday Market takes a break due to flooding, a brand-new holiday market is lighting up the Deer District.
- The Jingle Bus returns Nov. 20, offering a 40-minute narrated tour of Downtown Milwaukee’s holiday lights, departing from the new Warming House at Red Arrow Park with complimentary cocoa and cookies from Biggby Coffee.
- Wild Lights at the Zoo: Opening-night drone show (Nov. 21), expanded drive-thru nights (Nov. 29; Dec. 7, 14, 21), an adults-only Cheers! Wild Lights event (Dec. 11), and the first-ever Dogs After Dark night (Dec. 17) with photo ops, Santa visits, and pup treats.
Best Holiday Lights in Milwaukee & SE Wisconsin (Updated for 2025)
Brew some hot cocoa, bundle up, and get ready for a magical adventure through Milwaukee’s best Christmas lights this season. Find free displays in the heart of downtown, dazzling drive-through and walk-through shows, and more.
Free Holiday Events in Milwaukee
Looking for festive fun that won’t cost a thing? Check out our roundup of Free Holiday Events Around Milwaukee for light displays, parades, and Santa sightings the whole family will love.
Magical Christmas Events & Winter Experiences
From cozy Santa cruises and historic holiday villages, to performance of the “The Nutcracker” and train rides to Santa’s workshop, these magical holiday experiences will fill your family’s season with joy and wonder.
Holiday Shows in Milwaukee
This holiday season, Milwaukee’s stages come alive with festive, family-friendly holiday shows. From dazzling acrobatic performances to timeless holiday classics, there’s something for everyone to enjoy.
Where to Meet Santa in Milwaukee
Whether you’re looking for a cozy fireside chat, free holiday photo ops, or magical experiences with the big man in red, we’ve got the scoop on the best places to meet Santa in Milwaukee.
Santa’s Mailboxes Around Milwaukee
From the charming Cathedral Square Park to the Pfister Hotel’s grand lobby, we’ve rounded up the best bright red Santa’s Mailboxes where your little ones can send their letters straight to the North Pole. Some mailboxes even promise a personalized reply from Santa himself – no postage needed!
Christmas Tree Lightings Around Milwaukee
From downtown to neighborhood gatherings, Milwaukee’s Christmas tree lightings will dazzle you and your family. We’ve gathered a list of the top tree lighting events—organized by month—to make it easy for busy parents to plan.
Milwaukee Christmas Parades
It’s time to mark your calendars for Milwaukee’s magical Christmas parades! These events are more than just parades—they’re a celebration of community spirit, family fun, and holiday cheer, featuring festive lights, joyful music, and visits from Santa himself.
Milwaukee Christmas Markets
Milwaukee’s Christmas markets are back, filling the air with the rich aroma of hot pretzels, spiced mulled wine, and cinnamon-roasted nuts. From traditional Christkindlmarkts to local artisan fairs, these family-friendly markets bring the magic of the season to life.
Christmas Tree Farms Near Milwaukee
Looking for the perfect Christmas tree near Milwaukee? These family-owned tree farms in the area offer fresh-cut and choose-and-cut options, plus festive activities like hayrides, hot cocoa, and even visits from Santa! Make lasting holiday memories as you find the perfect tree to bring home.
Festive Holiday Restaurants
From cozy, heated huts to meet-and-greets with Santa, these festive Milwaukee restaurants offer unforgettable experiences where families can enjoy seasonal decor, delicious food, and a warm holiday atmosphere.
Gingerbread Displays Around Milwaukee
Looking for an enchanted holiday outing? Check out our guide to the Sweetest Gingerbread Displays Around Milwaukee for the whole family!
Horse-Drawn Sleigh Rides Near Milwaukee
It’s lovely weather for a sleigh ride in southeastern Wisconsin! Just a short drive from Milwaukee, you’ll find magical sleigh and sled rides through snow-covered orchards, scenic woodlands, and twinkling holiday light displays.
Milwaukee Holiday Gift Guide 2025
Introducing our 7th Annual Milwaukee Holiday Gift Guide! This year, we’re spotlighting meaningful, local gifts, from playful memberships and enriching experiences to unique gifts from Milwaukee’s small businesses.
Holiday Photo Spots Around Milwaukee
From twinkling downtown displays to cozy Christmas corners, these holiday photo spots around Milwaukee are full of charm and cheer — ideal for your next Instagram post or family holiday card.
Milwaukee Chanukah Events
From menorah lightings and concerts to exciting gelt drops and family-friendly celebrations, there’s something for everyone to enjoy. Check out our Chanukah Events roundup for all the details and start planning your Festival of Lights!
Looking for even more festive fun? Visit our Milwaukee Events Calendar to stay up-to-date with all the holiday happenings around Milwaukee!
In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place.
In 2019, she published “Exploring Milwaukee WIth Kids”, a comprehensive Milwaukee travel guide for families and kids.
She appears regularly on WISN News, Fox 6’s ‘Real Milwaukee’, B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News.
Calie is available for hosting, moderating and media appearances.
