Nine Day Trip Ideas in the Milwaukee, Southeast Wisconsin Area

Editor’s note: A previous version of this story included incorrect information about Port Washington Breakwater Lighthouse operations, based on information from two sources. However, an Ozaukee County representative acknowledged that the information was outdated. The story has been updated

You don’t have to travel that far to take a vacation, especially not in southeastern Wisconsin.

Here are nine day trip ideas to explore and relax with events, historic sites and plenty of photo opportunities. Some suggestions can be visited at any time of the year, while others are more specific to the season.

1. Old World Wisconsin to Eagle

Have you ever had the impression of belonging to another period? Step into Dairyland’s past at Old World Wisconsin, W372 S9727 Highway 67, Eagle, and discover what life was like in the late 1800s and early 1900s.

Sixty restored historic buildings sit on more than 600 acres connected to gardens and trails, according to the Old World Wisconsin website. It’s more than still scenes from days gone by. Instead, visitors can interact with costumed staff, share the history of the place, and talk about life. Don’t just watch and listen; visitors young and old can help with household chores and cooking, create crafts and discover trades.

Crossroads Village offers a main street area for a small town living experience. Visitors can shop at the general store, visit the blacksmith, and tour the homes and farms of Irish, Pomeranian, Polish, Hessian, Finnish, Danish, and Norwegian immigrants, to name a few.

Daring visitors can also hop on a high-wheeled bicycle.

Old World plans to reopen for the season on April 30. Learn about seasonal pricing, hours and more at

2. The “Da Crusher” statue in South Milwaukee

Lisowski family unveil life-size statue of Reggie

A life-size bronze statue commemorating South Milwaukee resident and professional wrestler Reggie “Da Crusher” Lisowski stands in downtown South Milwaukee near Milwaukee and 11th Avenue. The statue is there year-round, but the best time to visit “The Man Who Made Milwaukee Famous” is during Crusherfest.

Beer, kids, polka music as well as live wrestling and industry legends all feature at the annual event. The first Crusherfest was held in June 2019. The festival was canceled in 2020 due to the pandemic but returned in October 2021. Crusherfest will be held again in the fall for 2022 due to major renovations and construction that the city ​​is winding down on the festival grounds, according to Crusher Foundation President and South Milwaukee City Attorney Chris Smith.

The Crusher statue was funded by a $40,000 GoFundMe campaign launched by Smith.

For more information, visit

As an extra, cross the street and you’ll find the Bucyrus Club, 1919 12th Ave., home to the Bucyrus Museum, showcasing some of South Milwaukee’s manufacturing history. It was the Bucyrus company that built the shovels that dug the Panama Canal.

3. Cedarburg Strawberry Festival

Another festival worth seeing is the Strawberry Festival in Cedarburg. Ask any longtime resident, and they’ll tell you the festival is legendary.

The 36th Annual Strawberry Festival, scheduled for June 2021, has been canceled due to the ongoing COVID-19 pandemic. Typically, 100,000 people attend the festival to enjoy strawberries, live music, around 300 artist exhibits and more along Washington Avenue, according to the Cedarburg Art Museum.

The 2022 festival is scheduled for June 25 and 26.

For more information, visit

4. The elegant farmer’s wife of Mukwonago

The Elegant Farmer is located at 1545 Main St., Mukwonago.

After filling up on strawberries, it might be a good idea to grab some dessert, and what better way to eat it than in a paper bag? No seriously.

The Elegant Farmer at Mukwonago, 1545 Main St., is known for its apple pie in a paper bag. Sounds weird but should be tried before it’s trashed. Originally a family dairy farm in 1946 by brothers Dave and Elmer Scheel, The Elegant Farmer sells vegetables and fruit on the 65-acre property. Customers can also purchase baked goods and deli offerings. A pick-your-own concept allows visitors to go to the fields to pick strawberries, apples and pumpkins, depending on the season.

For those who can’t make it to The Elegant Farmer, apple pie in a paper bag and other offerings are available at 400 locations, including markets and grocery stores in Wisconsin, Illinois , of Michigan and online at

The Elegant Farmer hosts various events throughout the year, including National Pie Day, Maple Festival, cheese sales and more. See details at

5. Oconomowoc Wizard of Oz Square

A mural has been added in Wizard of Oz Square, next to Oconomowoc Town Hall.

From Wisconsin’s past to the wonderful Land of Oz, step into the classic story without the threat of a house falling on you. Oconomowoc’s Wizard of Oz Square features statues of the film’s characters and a new mural that commemorates the classic 1939 film, which some say originated in Oconomowoc.

A small portion of the Yellow Brick Road has been recreated to complement Dorothy, Toto, the Tin Man, the Scarecrow, the Cowardly Lion, the Wicked Witch of the West and the Wizard of Oz.

“We did a bunch of research on what was going to be best based on what the statues were going to be,” said David Batzner, co-owner of DNA Landscaping. “We didn’t just want it to be yellow. We wanted a design, a bit of fluidity. It’s just like in the movie.”

6. Lapham Peak in Delafield

A drone provides an aerial view of artificial snow along the ski slopes at Lapham Peak in Delafield on Tuesday, Dec. 17, 2019.

While in Lake Country, consider stopping at the Lion who claims to be King of the Forest in the Land of Oz, you can try playing the part in the Lapham Peak unit of Kettle Moraine State Forest in Delafield, one mile south of I-94 from exit 285, Highway C. The peak is named after Rise Lapham, a self-taught naturalist and scientist, according to the Milwaukee Encyclopedia.

Visit the 45-foot observation tower atop Waukesha County’s highest point. Hike, backpack, or mountain bike the entire area during the non-snowy months or cross-country ski the trails in the winter.

SummerStage is open during the summer. The outdoor stage is approximately 300 meters from the Evergreen parking lot. Music, theater and more are offered on stage; find out what’s happening and when at

7. Wehr Nature Center in Franklin

Waterfall at the Wehr Nature Center in Franklin.

For a slightly more guided tour of the wonders of the natural world, visit the Wehr Nature Center in Franklin. Located on 220 acres in Whitnall Park, the Wehr Nature Center offers 5 miles of walking trails with meadows, wetlands, woodlands and Lake Mallard – complete with sundeck.

Visitors can learn about a variety of wild plants and animals through rotating exhibits. Enjoy a fire pit (reservations required) near an outdoor amphitheater, which allows for different forms of educational entertainment, according to the Friends of Wehr Nature Center.

Are the kids coming? An early childhood playground, built in 2011, includes a sandbox, stepping stones and a log cabin.

Wehr Nature Center is open year-round from 8:30 a.m. to 4:30 p.m. seven days a week. Visit for upcoming events.

8. Port Washington Breakwater Lighthouse

Port Washington Lighthouse Walkway.

For those who prefer to be on the water rather than in the woods, the Port Washington Breakwater Lighthouse is a great idea for a day trip – if you’re up for a little stroll.

The lighthouse, completed in 1935, sits 2,500 feet along a breakwater made of steel decking, rocks and concrete, according to the Ozaukee County website. A red light, classified as a harbor light, flashed every six seconds and was visible from boats up to eight miles from the harbor.

Every 30 seconds, a fog horn sounded twice from the top of the lighthouse, from April to November, when the lighthouse was last in use.

The lighthouse itself is not open for tours, but visitors can get up close to take photos.

9. Learn more about Waukesha native Les Paul

Les Paul holds his

Les Paul is a part of Wisconsin history, and fans of his work can visit the Les Paul Memorial burial site at Prairie Home Cemetery, 605 S. Prairie Ave., Waukesha. The “Magician of Waukesha” memorial is in the eastern part of Section 5 of the cemetery. It features a hand carved guitar and a signature carved into a granite stone.

Fans can learn more about Les Paul at the Wizard of Waukesha exhibit at the Waukesha County Museum which is open from 1 to 4 p.m. Thursday and Friday and 10 a.m. to 4 p.m. Saturday.

Traveling between the tomb and the museum, you can wander the streets of downtown Waukesha, where you’ll find 10-foot-tall fiberglass guitar sculptures painted by local artists. Murals focused on Les Paul and Waukesha history are also prominently displayed throughout the Walldogs painted area.

To find the guitars and murals more easily, has a map at

Waukesha-born Paul is known for many things, including solid body electric guitar, overdubbing, and multitrack recording techniques. He is also known for the Les Paul guitar introduced by the Gibson Guitar Co. in 1952. Paul was also a TV radio star in the early 1950s with his wife, Mary Ford.

Paul died on August 12, 2009 in New York at the age of 94.

Contact Erik S. Hanley at (262) 875-9467 or [email protected] Like his Facebook page and follow him on Twitter at @ES_Hanley.

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