10 Best Road Trips from Milwaukee for a Family Weekend Getaway

 1. Valparaiso, Indiana  

Distance: 146 miles; Driving time: 2 h 33 min.

Valparaiso is a city and the county seat of Porter County, Indiana, United States. 

Start your adventures with a tour of the vibrant art scene that includes the Porter County Museum and the Brauer Museum of Art Center for the Arts. 

Take in a show at the Chicago Street Theatre or a musical performance that warms your heart at the Memorial Opera House. 

If you enjoy outdoor excursions, you can walk the trails at Rogers-Lakewood Park or tour the blooming flowers at Taltree Arboretum and Gardens.

 2. Chicago, Illinois 

Distance: 92 miles; Driving time: 1 h 34 min.

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. 

Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. 

Don't miss to visit The Art Institute of Chicago, Museum of Science and Industry, and 360 Chicago Observation Deck.

 3. Baraboo, Wisconsin 

Distance: 117 miles; Driving time: 1 h 48 min.

Explore Baraboo’s greatest natural attraction in Devil’s Lake State Park. 

Learn about circus clowns and clowning and the history of clowns in International Clown Hall of Fame and Research Center. 

Visit Circus World Museum for its vast grounds house a profusion of circus memorabilia, exhibits and live shows showcasing the history of circuses. 

Before hitting the road, make a stop at the Baraboo Bluff Winery, a family-run winery that offers fantastic views and three tasting bars for your winning pleasure.

 4. Wisconsin Dells, Wisconsin 

Distance: 123 miles; Driving time: 1 h 55 min.

Wisconsin Dells, a family-fun destination any time of year. Lying along the banks of the Wisconsin River, Wisconsin Dells takes its name from the towering sandstone formations–or dells–that line the river’s banks and were carved out during the last ice age. And as the “Waterpark Capital of the World,” Wisconsin Dells offers year-round watery fun at over 20 indoor and outdoor water parks and entertainment centers where gnarly waterslides, looping tube rides, lazy rivers and wave pools thrill and delight kids of all ages.

 5. Minocqua, Wisconsin 

Distance: 254 miles; Driving time: 3 h 56 min.

The Minocqua area offers dozens of activities and attractions that your kids will love! Here are just a few of top things to do. 

Northwoods Zip Line offers several canopy tour options for kids as young as three. Trek across adventure bridges, cruise over a lake, and for the competitive family, check out the dual race zip line. 

Bearskin State Trail, grab your bikes and explore this 18-mile crushed granite trail. Running along a former rail corridor, the trail crosses 13 trestle bridges and offers the opportunity to see a variety of wildlife, including deer and bald eagles. 

The second largest zoo in the state, Wildwood Wildlife Park & Safari is the perfect place for kids of all ages. 

Head over to one of the area's great beaches. You can choose Torpy Park, Brandy Park or Clear Lake, which offer picnic areas and restrooms, among other amenities. Build a sandcastle, bury your best friend in the sand, play some Frisbee, just Don't forget the sunscreen!

 6. Madison, Wisconsin 

Distance: 80 miles; Driving time: 1 h 19 min.

The sprawling University of Wisconsin sets the tone for this college town of cafes, bookstores, brewpubs, numerous restaurants (more per capita than anywhere else in the U.S.) and a good share of cultural and historical attractions. 

Wisconsin State Capitol, free guided tours highlight architecture and art - mosaics, stained glass and murals.

Chazen Museum of Art, galleries display African, Asian and 21st-century international works at this museum on the University of Wisconsin campus).

Olbrich Botanical Gardens, the 16 acres encompass a rose garden, conservatory, sunken garden, and Thai pavilion and garden.

 7. Green Bay, Wisconsin 

Distance: 117 miles; Driving time: 1 h 47 min.

Whether you're looking for concerts, festivals, outdoor celebrations or sporting events, Greater Green Bay has something for everyone to enjoy. 

Surround yourself with friendly pollinators and the plants they love at the Green Bay Botanical Garden's Butterflies & Blooms exhibit. 

For over a century, Bay Beach Amusement Park has provided many families fun and enjoyment along the shores of the Bay of Green Bay. New this year for you to try is the 100-foot-tall Big Wheel.

 8. Door County, Wisconsin 

Distance: 117 miles; Driving time: 1 h 47 min.

Door County is often called the “Cape Cod of the Midwest.” And it’s true that both places occupy a peninsula dotted with picturesque villages, contain a higher-than-average number of fudge shops per capita, and draw convoys of city dwellers on high-season weekends. Visit Ridges Nature Center & Baileys Harbor Lower Rangelight, Climb the Cana Island Lighthouse, View sunset at Anderson's Dock, Ferry to Washington Island and so on.

 9. Oshkosh, Wisconsin 

Distance: 93 miles; Driving time: 1 h 37 min.

Oshkosh boasts a variety of things to see and do for the whole family, from historic sites and cultural activities to outdoor recreation and sports. Oshkosh is home to several brewing companies, where you can taste some of the region’s top craft beers, as well as beautiful parks and green spaces for picnicking and fun in the sun, art galleries, museums and educational centers, and water parks. Top 3 attractions are EAA Aviation Museum, Menominee Park, and Paine Art Center and Gardens.

 10. Gurnee, Illinois 

Distance: 51 miles; Driving time: 52 min.

Gurnee, midway between Chicago and Milwaukee, is probably best known as the home of Six Flags Amusement Park and the Gurnee Mills shopping outlet. Now Midwesterners looking for a little rest and relaxation can sample the town's top attraction, the KeyLime Cove hotel and water park, which also features a spa, shopping and six restaurants.

These 10 top places are within 260 miles away from Milwaukee and make perfect family weekend getaways, whether it’s centered around outdoor activities, charming beaches or natural landscapes. 

Renting a Car for Family Road Trip from Milwaukee

If you need to rent a car to start your weekend road trips, you can visit Dollar Rent A Car, Europcar, Avis, Thrifty, Hertz, Sixt Rent A Car, CarRentals.com. Don't forget to earn up to 6% cashback from Extrabux! 

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