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Seasonal Fun

Explore seasonal family fun in Milwaukee throughout the year! From summer splash pads and water parks to fall apple orchards and pumpkin patches, winter skiing and sledding, and festive holiday events, find the best activities for families in every season.

Families sledding at one of Milwaukee’s most popular winter hills. Milwaukee transforms into a winter wonderland every year, and there’s no better way to enjoy it than sledding. Whether you’re looking for thrilling hills for older kids or gentle slopes for toddlers, Milwaukee offers a variety of options. Here’s a guide to the best sledding hills...
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Red Arrow Park is Milwaukee’s most popular free outdoor skating rink. Looking for the best ice skating rinks in Milwaukee this winter? Whether you’re planning a family outing, a first time on the ice with kids, or a fun way to get outside during the colder months, Milwaukee offers a wide mix of indoor and outdoor ice skating...
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Winter in Milwaukee is a season of celebration, where the cold brings people together for creative, family-friendly fun — especially when ice sculptures and winter festivals take center stage. From live ice carving demonstrations to large-scale sculpture displays, these winter festivals feature some of the best ice sculptures in and around Milwaukee, many within an easy...
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Craving the best hot chocolate in Milwaukee this winter? You’re in the right place. When the Milwaukee chill sets in, nothing warms you up quite like a steaming cup of hot chocolate (or hot cocoa). Whether you’re searching for a cozy neighborhood café, an Instagram-worthy hot chocolate flight, or a rich European-style sipping chocolate, Milwaukee offers plenty...
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Start the new year with fresh air, giant kites, and a beloved Milwaukee tradition. The Cool Fool Kite & Snow Carving Festival returns to Veterans Park on New Year’s Day, inviting families to celebrate with colorful kites, live ice carving, and free winter fun along the Lake Michigan shoreline. Hosted by Gift of Wings and the Kite Society of Wisconsin & Illinois, this...
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LED Dancers at Chanukah Festival and Gelt Drop The Yard at Bayshore Whitefish Bay Wisconsin
Each year the Hoan Bridge lights up like a giant menorah for Hanukkah on the Hoan. Chanukah is just around the corner, and there are some truly amazing events lined up this year. We’ve got the scoop on the top 5 you won’t want to miss. So grab your calendars and let’s dive in! Looking...
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Updated November 2025 Quick Info for Parents Opening Day: TBD for 2025-26 season Cost: Free with your own skates; rentals start at $8–11 Extras: Polar Pals for kids, ADA ice sleds, skate sharpening Parking: Marcus Center garage + street parking nearby What’s New: Biggby Coffee is back for warm drinks + snacks inside the warming house Best Time to Go: Weekday...
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The holiday season is the perfect time to experience the magic of live reindeer in Milwaukee with your family. All around the city and southeastern Wisconsin, you’ll find festive events where kids can meet reindeer up close and capture holiday memories. From tree lighting ceremonies to special holiday gatherings, here’s your guide to reindeer events near Milwaukee this December. 1....
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Winter break offers a fantastic opportunity for kids to have fun, learn, and make memories outside the classroom. Milwaukee boasts a variety of Winter Camps designed to keep children entertained and engaged. Here’s a roundup of some exciting options! Looking for more camp opportunities? Be sure to attend our annual 2025 Summer Camp Fair, and...
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Santa Chalets at Natty Oaks in West Allis Milwaukee is full of cozy Christmas-themed restaurants, festive dining huts, and holiday pop-up experiences. If you’re looking for a spot that feels extra magical this time of year, this guide brings together the best places to eat, sip, and soak up the season. From heated chalets and...
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