Family-Friendly Day Trips From Milwaukee

Explore the best family-friendly day trips from Milwaukee! Discover fun and exciting destinations perfect for kids and parents alike, just a short drive away.

Nov

Best Playgrounds & Parks in Chicago for Kids (2026)

November 1, 2025Calie HerbstDay Trips From Milwaukee

Maggie Daley Park’s massive climbing towers and suspension bridges make it one of the top destination playgrounds in the U.S. Chicago has more than 500 parks, but not all are created equal when you’re exploring the city with kids. Whether you need a quick play break between attractions, a sprawling destination playground worth the detour,...

Oct

360 Chicago vs. Skydeck: Which Observation Deck Is Best for Kids?

October 23, 2025Calie HerbstDay Trips From Milwaukee, Family Vacation Spots

Lying on the glass floor of The Ledge, surrounded by sweeping views of downtown Chicago. When you’re planning a family trip to Chicago, chances are both 360 Chicago at the John Hancock Center and the Skydeck at Willis Tower pop up on your list. They both promise incredible views and unforgettable photo ops – but which one’s really worth it for...

Sep

Best Things To Do in Chicago With Kids (100+ Ideas for 2026)

September 13, 2025Calie HerbstDay Trips From Milwaukee

Navy Pier in Chicago is one of the most popular family attractions. Planning a family trip to Chicago? Whether you’re coming from Milwaukee or visiting from out of town, Chicago and its suburbs offer hundreds of kid-friendly attractions — from world-class museums and waterfront parks to epic playgrounds and creative indoor experiences. This guide brings together the best...

Aug

Bristol Renaissance Faire With Kids: Tips, What to Expect, and Parent Guide

August 29, 2025Calie HerbstDay Trips From Milwaukee

Kids watching the lively joust show at the Bristol Renaissance Faire. If you’re looking for a family day trip that feels totally different from everyday life, the Bristol Renaissance Faire in Kenosha is a great summer option. From July through Labor Day weekend, the wooded grounds transform into a lively 1500s-style village filled with performers, costumes, shows,...

Aug

International Crane Foundation in Baraboo: A Peaceful Day Trip for Families

August 24, 2025Calie HerbstDay Trips From Milwaukee

Kids play at the International Crane Foundation in Baraboo, WI. Just two hours from Milwaukee, the International Crane Foundation in Baraboo is one of Wisconsin’s most unique outdoor experiences — and a surprisingly calm, easy day trip with kids. It’s also the only place in the world where you can see all 15 species of cranes, including 11 that are...

Aug

Day Trip to Madison with Kids: Best Family-Friendly Stops & Outdoor Activities (2026)

August 21, 2025Calie HerbstDay Trips From Milwaukee

Is there anything better than a day in Madison? A few weeks ago, I spent a summer day there with my daughters (ages 9 and 11), and it reminded me just how much the city has to offer families. Even after living in Madison for six years as a college student and visiting many times...

Aug

Chicago With Kids: Top Attractions, Museums, and Suburban Gems (2026)

August 7, 2025Calie HerbstDay Trips From Milwaukee

Chicago is one of the most family-friendly cities in the U.S., with world-class museums, colorful immersive exhibits, and fun just waiting around every corner. And yes, it’s totally doable with kids. Whether you’re coming from Milwaukee for the day or flying in for a weekend, here’s a roundup of our favorite kid-friendly attractions in the...

Jun

A Free & Easy Day Trip: Henry Vilas Zoo in Madison

June 18, 2025Calie HerbstDay Trips From Milwaukee

Looking for an easy, low-cost day trip from Milwaukee? Add Henry Vilas Zoo in Madison to your list. It’s one of the only free zoos in the country—and it’s the perfect size for little legs. Here’s everything you need to know before you go: Admission is Always Free Henry Vilas Zoo is completely free and community-supported. No admission fees,...

Jun

5 Scenic Lighthouses to Visit in Southeastern Wisconsin (2025)

June 1, 2025Calie HerbstDay Trips From Milwaukee, Family Fun Hub

The history of Milwaukee is deeply rooted in commercial traffic on the Great Lakes. These towering lighthouses have been guiding ships safely to shore for centuries, and they’re also a great place to explore with your little ones. Older kids will especially love climbing to the top of a tower to take in some spectacular...

May

Bay Beach Amusement Park: The Ultimate Guide for Milwaukee Families (2026)

May 20, 2025Calie HerbstDay Trips From Milwaukee

The Big Wheel offers gorgeous lakeside views of Green Bay. Photo from Visit Green Bay Free Admission • 25¢ Tickets • Perfect for All Ages If you’re looking for a fun, affordable summer day trip from Milwaukee, Bay Beach Amusement Park in Green Bay is one of the best family destinations in Wisconsin. With free admission, free parking, and rides...

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