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Winter officially arrives this Sunday, and Christmas is less than one week away! Here are our top picks for making the most of this festive weekend:
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FEATURED: Holidays On The Hop
Holidays On The Hop (FREE!)
Date: Sunday, December 21, 2025, 4-6 p.m.
Location: Downtown Milwaukee
Hop aboard Milwaukee’s free streetcar for live holiday music and sweet treats! Each Sunday features new performers and free cookies for riders. It’s the perfect opportunity to see all the holiday lights downtown, or make a stop along the route for some hot cocoa.
👉 Get the full details.
TOP PICKS
Cocoa & Claus at Betty Brinn Children’s Museum
Date: Saturday, December 20, 2025, 9 a.m.-Noon
Location: Betty Brinn Children’s Museum, 929 E. Wisconsin Ave., Milwaukee, WI 53202
Enjoy Santa Story Times, build cocoa-catapults and tinker trees in the Be A Maker space, and snap a festive family photo with Santa! Hot chocolate from Stone Creek Coffee included.
👉 Learn more and get tickets.
Storytime With Santa at Discovery World
Date: Sunday, December 21, 2025, 11 a.m.-1:30 p.m.
Location: Discovery World, 500 North Harbor, Milwaukee, WI 53202
Join us in the theater for storytime and photos with Santa at 11:00 AM, Noon, and 1:00 PM. Between sessions, Santa will be spreading holiday cheer as he strolls throughout the building.
👉 Included with general admission — get tickets now!
Breakfast With Santa
Date: Various dates and times
Locations:
… and more! Enjoy delicious meals, festive activities, and magical moments with Santa Claus himself.
👉 Find a breakfast with Santa event.
Bedazzled Christmas Tree Painting on Canvas: Art Class at 3rd Street Market Hall
Date: Saturday, December 20, 2025, 2:30-4:30 p.m.
Location: 3rd Street Market Hall, 275 W. Wisconsin Ave., Milwaukee, WI 53203
Children’s Art Classes of Menomonee Falls is holding a workshop at 3rd Street Market Hall. It’ll be a festive afternoon full of Christmas tree painting, bedazzling, and yummy treats to enjoy! Recommended for ages 6 and up.
👉 Get creative.
FREE WINTER FUN
Kooky Cookie House at Shady Lane Greenhouse
Date: Open daily through the holiday season, 10 a.m.-3 p.m.
Location: Shady Lane Greenhouse, W172N7388 Shady Lane, Menomonee Falls, WI 53051
Kids of all ages will enjoy this opportunity to walk through and see the inside workings of this gingerbread cookie factory that has been refurbished by many passionate volunteers over the years. There are great photo opportunities, coloring pages, and more.
👉 Click here for more info.
Winter Solstice Celebration at Riveredge Nature Center
Date: Saturday, December 20, 2025, Noon-8 p.m.
Location: Riveredge Nature Center, 4458 County Hwy Y, Saukville, WI 53080
Awaken your curiosity, engage your body, and explore the beautifully restored Riveredge landscape through free self-guided and educator-led activities. Folks of all ages can discover a variety of ways to enjoy nature, including hiking, crafting, stargazing, a bonfire, and more.
👉 Pre-register by December 19 at 11:59 p.m. (or at the program if spots are available).
Winter Fest at Havenwoods State Forest
Date: Saturday, December 20, 2025, 10 a.m.-2 p.m.
Location: Havenwoods State Forest, 6141 N. Hopkins St., Milwaukee, WI 53209
Enjoy hot chocolate and s’mores, meet animals, listen to Nature Tales, make crafts and memories, and more in Wisconsin’s only urban state forest. This free, family-friendly event will be held rain or shine.
👉 Learn more about what you’ll find on the walk.
FOR OLDER KIDS
Holiday Pops by Milwaukee Symphony Orchestra
Date: December 13-21, 2025 (various showtimes)
Location: Bradley Symphony Center, 212 W. Wisconsin Ave., Milwaukee, WI 53203
Milwaukee’s cherished musical holiday tradition features classic holiday tunes, carols, and festive sing-alongs performed by MSO.
👉 Find a showtime for your family.
Champions of Magic: Holiday Spectacular at the Riverside Theater
Date: Saturday, December 20, 2025, 7:30 p.m.
Location: Riverside Theater, 116 W. Wisconsin Ave., Milwaukee, WI 53203
Celebrate the season with dazzling illusions; breathtaking, grand-scale magic; and festive surprises for the whole family. This high-energy, interactive show blends humor, jaw-dropping magic, and holiday cheer.👉 Prepare to be amazed.
THERE’S MORE! Find holiday fun galore on the Events Calendar! You can even filter by location, price, and more.
Kids’ Disco on 88.9 FM Radio Milwaukee
Celebrate the start of the weekend and the end of the wiggles with Dori Zori and Kids’ Disco on 88.9 FM Radio Milwaukee (Saturdays, 9-10 a.m.)! Enjoy an hour long non-stop mix of music for the whole family to enjoy.
Ready for More Family Fun?
Milwaukee is packed with even more exciting activities and hidden gems for you to explore with your family this season. Whether you’re looking for spontaneous outings or planning ahead, we’ve got you covered!
📅 Explore Our Events Calendar
From seasonal celebrations to ongoing attractions, our Events Calendar is your go-to guide for family-friendly happenings in and around Milwaukee. Discover new experiences every day, tailored just for you.
☀️ Fall Fun
Check out our Milwaukee Fall Fun Guide to uncover the best apple orchards, pumpkin patches, corn mazes, and more!
🎡 Don’t Miss Our Top Picks!
Looking for more must-visit spots? Dive into our guides on:
- Milwaukee’s Best Playgrounds – Discover the most fun and unique play areas for kids of all ages.
- Kid-Friendly Restaurants – Enjoy a meal where the whole family is welcome.
- Indoor Playgrounds – Perfect for those rainy or chilly days.
- Top Museums for Kids – Unleash your child’s curiosity with engaging exhibits.
- Free & Affordable Activities – Have a blast without breaking the bank.
📬 Join Our Community!
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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.
