Seasonal Family Fun in Milwaukee: Activities for Every Season

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.

May

5 Best Summer Concerts for Kids & Families in Milwaukee (2026)

May 8, 2025Calie HerbstSummer Fun

Summer in Milwaukee means music in the parks, food on the lawn, and kids dancing barefoot in the grass. While there are concerts happening all over the city, some are especially welcoming to families with young kids. Here are five local concert series for families that make it easy (and fun) to bring the whole crew along! 💡Love free live music? Check out our roundup of free summer festivals happening in Milwaukee this summer. Quick Picks: Best Summer Concerts for Kids (2026) Most interactive: Wonderful Wednesdays Best playground access: Chill on the Hill Best teen-friendly vibes: Washington Park Wednesdays Best views: Skyline Music Series (TBD for 2026)...

May

25 Best Splash Pads & Wading Pools Around Milwaukee (2026)

May 5, 2025Calie HerbstSummer Fun

The heat of summer is just around the corner, and there’s no better time to hit the nearest watering hole and cool off. Splash pads and wading pools offer families with young children the perfect antidote to the summer heat. Splash pad season typically runs from Memorial Day through Labor Day (see exceptions below). Here...

May

‘Big Truck Day’ Rolls Into Red Arrow Park This May (Free!)

May 1, 2025Calie HerbstSpring Adventures

Saturday, May 17, 2025 | 11:00 a.m. – 2:00 p.m.📍 Red Arrow Park, Downtown Milwaukee🎟️ FREE and open to the public Big Truck Day is back for its fourth year in a row, rolling into Red Arrow Park on Saturday, May 17 from 11:00 a.m. – 2:00 p.m., just in time to kick off National Public Works Week. This free event...

Apr

Family Camping in Wisconsin: What’s New for Summer 2025

April 24, 2025Calie HerbstSummer Fun

Grand Valley Campground in Dalton Wisconsin’s family-owned campgrounds are rolling out a variety of new experiences for the 2025 camping season, from lounging pools with built-in coves to foam cannon parties, floating water playgrounds, and live concerts in the woods. Many parks are also expanding with new cabins, RV sites, and family-friendly amenities. In this...

Apr

25 Fun and Free Spring Activities For Kids (2026)

April 3, 2025Calie HerbstSpring Adventures

Rainy days are made for puddle jumping—simple spring fun! Spring is in full bloom—the flowers are vibrant, the sun is shining, and the air feels crisp and refreshing. But for parents, the season often brings a familiar question: How can I keep my kids entertained and active during these spring months, especially during spring break?...

Kite Festival Milwaukee Wisconsin lakefront Veterans Park

Apr

The Family Kite Festival Returns to Milwaukee’s Lakefront

April 3, 2025Calie HerbstSummer Fun

For nearly four decades, Milwaukee’s lakefront has been the setting for one of the most vibrant and high-flying weekends of the year. Now in its 38th year, the Gift of Wings Family Kite Festival, presented by IKEA, returns to Veterans Parkon Saturday, May 24 and Sunday, May 25, 2025. Festivities begin at 10:00 a.m. each day, with events running through 6:00 p.m. on Saturday and 5:00...

Mar

Easter Events in Milwaukee: 10 Fun Things To Do With Kids (2026 Guide)

March 21, 2025Calie HerbstSpring Adventures

Over 4,000 eggs are hidden at the annual Easter Egg Hunt at the Harley-Davidson Museum. Updated annually before Easter Spring is in the air, and Easter events start popping up all around Southeastern Wisconsin. This guide highlights popular, recurring family-friendly traditions so you can plan ahead — and we’ll update each listing with exact dates as they’re...

Mar

Dairy Queen Free Cone Day 2026: Date, Details & What Families Need to Know

March 16, 2025Calie HerbstSpring Adventures

Dairy Queen’s Free Cone Day is back for 2026. The first day of spring is getting a little sweeter—Dairy Queen Free Cone Day is officially back for 2026. Each year, families across Milwaukee look forward to this feel-good tradition, and it’s an easy way to kick off warmer days with something simple and fun. Here’s...

Mar

10 Perfect Milwaukee Pie Stops to Celebrate Pi Day (2025)

March 11, 2025Calie HerbstSpring Adventures

It’s Pi Day, celebrated worldwide on March 14th (3.14, get it?). Pi Day isn’t just for mathematicians; it’s a day that brings people together over the universal love for pie, whether sweet or savory. And what better way to celebrate than by supporting our local bakeries and pie shops? Many local spots are celebrating with...

Mar

Spring in Milwaukee with Kids: The Ultimate 2026 Family Guide

March 6, 2025Calie HerbstSpring Adventures

Spring in Milwaukee is a season of new beginnings – and new family adventures. Whether you’re celebrating St. Patrick’s Day, hunting for Easter eggs, or strolling through blooming tulip fields, the city comes alive with events and activities for kids of all ages. This guide pulls together the best things to do in March, April,...

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