The holidays are officially here, and it’s time to put the “most” in the most wonderful time of the year.
Find the best holiday lights, the most magical experiences, the cutest Santa’s mailboxes, and more.
Consider this your holiday headquarters, Milwaukee!
New This Year
Milwaukee Downtown, BID #21 is celebrating this year’s 25th anniversary of the Milwaukee Holiday Lights Festival, presented by Johnson Financial Group, with a new attraction along Wisconsin Avenue and Water Street.
All season long, residents and visitors will have the opportunity to explore a brand-new collection of 15 larger-than-life, hand-painted ornaments as part of the new Ornament Trail.
Holiday Lights
From Wild Lights at the Milwaukee County Zoo, to the Milwaukee Holiday Lights Festival downtown, to Candy Cane Lane in West Allis, and all the way out to Country Christmas in Pewaukee and Enchantment in the Park in West Bend, we’ve got the lowdown on the most bedazzling holiday lights in Southeastern Wisconsin.
See the 15 Best Milwaukee Holiday Lights Displays >>
Magical Holiday Experiences
Explore the new Enchant Christmas in Franklin!
Plus, see the CP Holiday Train pull into town, take a Santa Cruise around Lake Geneva, stroll through the poinsettias at the Domes Holiday Show, watch the fireworks at Christmas in the Ward, and more.
See all 10 Magical Holiday Experiences Your Kids Will Love >>
Live Theater
A live theater production is sure to spark your holiday spirit, and there’s no shortage around Milwaukee.
From a casual Pajama Jamboree to a fancy outing for “The Nutcracker” (reimagined this year!), find a live show that’s just right for you.
5 Live Holiday Shows Your Kids Will Love >>
Meet Santa
Santa has landed safely in Milwaukee!
He’ll be making stops all over town, including Santa’s Cavalcade in downtown Milwaukee, the Pabst Mansion, the Pfister Hotel, and more.
See the 10 Best Places to Meet Santa Around Milwaukee >>
Santa’s Mailboxes
Make your list, and check it twice! Santa Claus is placing his bright red mailboxes all over town for your children’s letters and wish lists.
Ride the hop to Cathedral Square Park, drop your letter off in the fancy lobby of the Pfister Hotel, or find another mailbox near you!
See all 9 Mailboxes in Milwaukee >>
Tree Lightings
Milwaukee is lit! (Literally.)
We found Tree Lightings happening all over the city to dazzle you and your family. They are listed in chronological order and by month, for maximum busy-parent convenience.
See all 10 Dazzling Christmas Tree Lightings Around Milwaukee >>
Christmas Tree Farms
If you’re looking for a good place to get a real Christmas Tree, we found 7 Christmas Tree farms to “pick” from. All of them family-owned and open for business in 2023.
Find one near you >>
Sleigh Rides
It’s lovely weather for a sleigh ride in southeastern Wisconsin! Take a magical sleigh or sled ride in the great outdoors. From Apple Holler to Roden Barnyard Adventures, here are some good options for this unique wintry experience.
2023 Experience Gift Guide
This year, we’re highlighting unique experiences from 14 local partners that make great gifts, including Bug & Goose Play Cafe, Little Sprouts Play Cafe, First Statge,School of Rock in Shorewood, and more.
See all 14 Experiences That Make Great Gifts >>
Toy Stores & Children’s Boutiques
We know our readers love to shop local. Have you heard of these 10 local toy stores and children’s boutiques? They’re thoughtfully curated and family-owned.
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.
