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.
These holiday-themed spots will bring a little sparkle to your dining experience this season!
For even more holiday fun ideas, don’t miss our Holiday Fun Guide and see our list of 25 Kid-Friendly Restaurants Around Milwaukee for family-friendly dining year-round.
At Random Bar’s “Enchanting Magic Forest”
2501 S Delaware Ave., Milwaukee WI 53207
Step into the whimsical “Magic Forest” at At Random Bar, where the patio transforms into a breathtaking winter wonderland.
Twinkling lights, festive decorations, and cozy heated huts make this an ideal spot to kick off the holidays in style.
The heated huts are by reservation only, so be sure to book early and secure a space for the family to sip on hot cocoa (or enjoy other seasonal drinks) under the dazzling lights.
Family Details: Well-behaved children are welcome in the Magic Forest area until 8 p.m. Enjoy the festive ambiance from your private, heated hut or opt for an outdoor table, available on a first-come, first-served basis.
Zócalo Food Truck Park
636 S 6th St, Milwaukee, WI 53204
Located in the heart of Walker’s Point, Zócalo Food Truck Park combines Milwaukee’s best food trucks with a cozy, festive atmosphere.
Reserve one of the heated huts for up to 10 people and enjoy a wide range of food options from vendors like Mazorca Tacos, Hot Box, and Anytime Arepa.
This vibrant and bustling spot is perfect for families who want to explore different cuisines while staying warm in the hut and soaking in the holiday spirit.
Family Details: Food trucks close at 9 p.m., so if your hut reservation extends later, place food orders early. Huts are available for 90-minute sessions.
Santa Chalets at Natty Oaks
11505 W National Ave, West Allis, WI 53227
Celebrate the holidays with Santa at Natty Oaks! Families can book a private chalet where they can dine and spend quality time with Santa himself, creating memories in a cozy setting surrounded by festive lights and holiday cheer.
Each chalet comfortably seats up to six people, providing an intimate setting for little ones to chat with Santa and even snap a few photos. The 12,000 square feet of Christmas lights add to the magic, making this a holiday experience your family won’t want to miss.
Family Details: Santa Chalets are available on Saturdays, as well as Tuesday through Thursday. Be sure to check Natty Oaks’ schedule for availability and reserve early for a chance to meet Santa in a beautiful, holiday-themed chalet.
Erv’s Mug
130 W Ryan Rd, Oak Creek, WI 53154
Since 1979, Erv’s Mug has been a beloved, family-owned spot known for its cozy, nostalgic atmosphere and welcoming service. Each holiday season, Erv’s transforms with elaborate holiday decor, covering the walls and ceiling with festive ornaments that bring the space to life.
Visitors can enjoy the lively holiday atmosphere, a menu full of pub favorites, and an extensive selection of craft beers. Their Friday Fish Fry is especially popular, and with the festive decorations, it’s a must-see during the holiday season.
Family Details: Erv’s may be a restaurant/bar, but its warm, friendly environment makes it a comfortable choice for all ages. Arrive early if you plan to visit on weekends to avoid the wait, as it’s a popular destination this time of year.
Tin Widow’s Miracle Pop-Up Cocoa Bar
Saturdays in December, 11 a.m.-3:30 p.m. | Tin Widow, 703 S. Second St.
Although it’s a whiskey bar by night, the Tin Widow’s Miracle Pop-Up Cocoa Bar is a perfect family outing. This festive cocoa bar offers crafts, Santa photo opportunities, and holiday merch in a magical, light-filled setting. Adults can enjoy craft cocktails while the kids sip cocoa. Free admission.
Fox & Hounds Restaurant & Tavern
1298 Friess Lake Rd, Hubertus, WI 53033
Nestled in the rolling hills of northern Kettle Moraine, Fox & Hounds Restaurant & Tavern is a historic gem dating back to 1933.
This charming cabin-turned-restaurant comes alive with seasonal decorations, creating a cozy holiday atmosphere that’s perfect for families.
Known for its hearty Sunday Brunch, Friday Fish Fry, and an impressive selection of steaks and seafood, Fox & Hounds offers a memorable dining experience in a beautifully decorated setting.
The restaurant’s themed rooms—including the Hunt Room, Oak Room, and Garden Room—add a unique touch to the festive ambiance.
Family Details: Located in Hubertus, WI, just two miles east of Holy Hill, Fox & Hounds is a welcoming choice for families who want a special holiday meal in a warm, rustic atmosphere.
6. Milwaukee Public Market
From December 6 to December 12, the Milwaukee Public Market becomes a holiday wonderland with the MATC Parade of Gingerbread Houses.
Culinary students from the Milwaukee Area Technical College Bakery Program present a dazzling array of gingerbread houses, crafted with intricate details and festive flair.
The gingerbread houses are displayed in the main atrium, and Santa’s mailbox is also available, so children can drop off their letters to Santa while enjoying the holiday decor.
Event Details: The gingerbread display is open during market hours, and admission is free.
These Milwaukee spots add extra cheer to the holiday season, with enchanting decor and family-friendly setups that create lasting memories for kids and adults alike.
If you’re exploring Milwaukee with the kids, consider adding Hot Cocoa Stops Along The Hop Streetcar Route to your itinerary or checking out Breakfast with Santa Options Around Town for even more holiday fun.
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
