The holiday season is here, and Milwaukee is brimming with festive activities for the whole family! From sparkling light displays and charming Christmas markets to meet-and-greets with Santa and magical winter events, there’s something special happening around every corner.
Consider this guide your go-to resource for making holiday memories—whether you’re looking for classic holiday traditions, new winter adventures, or simply want to soak up the spirit of the season.
Bundle up, grab some hot cocoa, and dive into our curated list of Milwaukee’s best holiday experiences. Happy holidays!
Best Holiday Lights
Brew some hot cocoa, bundle up, and get ready for a magical adventure through Milwaukee’s best Christmas lights this season.
Whether you’re exploring stunning free displays in the heart of downtown, discovering twinkling neighborhoods that glow with holiday spirit, or taking in dazzling drive-through light shows, we’ve curated the ultimate list for you.
Magical Holiday Experiences
Get ready, Milwaukee—this holiday season is packed with unforgettable magic for kids and families!
From awe-inspiring light displays to cozy Santa cruises and charming holiday festivals, we’ve rounded up the top festive experiences that will make spirits bright. Whether you’re taking a train ride to Santa’s Workshop, watching The Nutcracker come to life, or exploring historic holiday villages, these 10 unique events are sure to fill your family’s holiday with joy and wonder.
Holiday Shows
This holiday season, Milwaukee’s stages come alive with festive, family-friendly shows that promise to fill your heart with joy and magic! From dazzling acrobatic performances to timeless holiday classics, there’s something for everyone to enjoy.
Where To Meet Santa
Santa Claus is making his rounds in Milwaukee, bringing holiday cheer to kids and families across Southeastern Wisconsin!
Whether you’re looking for a cozy fireside chat or a photo with the big man in red, we’ve got the scoop on the best places to meet Santa this season. From free holiday photo ops to magical experiences with Mrs. Claus, here are all the top spots to find Santa this year!
Santa’s Mailboxes
This holiday season, Santa Claus is placing his bright red mailboxes all over the Milwaukee area for your children’s letters and wish lists! 🎅
From the charming Cathedral Square Park to the Pfister Hotel’s grand lobby, we’ve rounded up the best spots 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!
Tree Lightings
Milwaukee is truly lit this holiday season! From downtown to neighborhood gatherings, Milwaukee’s Christmas tree lightings will dazzle you and your family with magical moments and festive celebrations.
We’ve gathered a list of the top tree lighting events—organized by month—to make it easy for busy parents to plan and enjoy these joyful displays.
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.
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. Explore lively stalls packed with handcrafted gifts, unique finds, and delicious seasonal treats.
From traditional Christkindlmarkts to local artisan fairs, these family-friendly markets bring the magic of the season to life.
Find Milwaukee’s Best Christmas Markets >>
Christmas Tree Farms
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 Restaurants
The holiday season in Milwaukee brings festive magic to restaurants and eateries all around the city.
From cozy, heated huts to meet-and-greets with Santa, these four unique destinations offer unforgettable experiences where families can enjoy seasonal decor, delicious food, and a warm holiday atmosphere.
Gingerbread Displays
Looking for an enchanted holiday outing? Check out our guide to the 5 Sweetest Gingerbread Displays Around Milwaukee for the whole family!
Sleigh Rides
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. Bundle up, grab some cocoa, and enjoy a classic winter experience with family and friends.
Discover the Best Sleigh Rides Near Milwaukee >>
2024 Gift Guide
Introducing our 7th Annual Holiday Gift Guide! This year, we’re spotlighting meaningful, local gifts that create lasting memories—from playful memberships and enriching experiences to unique gifts from Milwaukee’s small businesses. Find something for every child on your list and support local favorites!
Festive 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 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.
