Working Vacation: Wisconsin

May 2022

Things to Do When You're Traveling Through - Restaurants, Sites in Wisconsin


Wisconsin’s largest city is on the western shore of Lake Michigan. Tour a brewery or the Harley-Davidson Museum. Visit the Milwaukee County Zoo or Milwaukee Public Museum. This city has theaters, outdoor festivals, and lots of great restaurants.

Nari Haig is the director of Milwaukee’s Morning Glory Art Fair. This year’s event is Aug. 13-14. “Wisconsin is a multi-season, comfortable, and approachable place to visit any time. Summers offer all the fairs, festivals, and farm markets you can imagine, along with thousands of lakes to visit. Winters allow visitors to embrace the outdoors or hunker down in a cozy spot. Spring and fall weather is for exploring without the extreme weather. Milwaukee has a solid theater presence, and Madison has its own cultural vibe,” Haig said.

Restaurants Haig recommends:

Cool sites Haig recommends: 

Josh Depenbrok is the public relations manager at the Milwaukee Art Museum. The art museum hopes to bring its Lakefront Festival of Art back in 2023. Depenbrok said Wisconsin is “America’s Dairyland — great food, great beer, great people.” 

Restaurants Depenbrok recommends: 

Jean Wells is a ceramicist who lives in Milwaukee. “State parks, lakes, and waterways are wonderful,” she said of the state. 

Wells recommends this site: 


Wisconsin’s capital is west of Milwaukee. This city has lots to offer, including entertainment, outdoor recreation, botanical gardens, a zoo, and the Dane County Farmer’s Market. Diana Jones, Sunshine Artist’s publisher, lived in Madison for 15 years and shares some of her favorite locations. 

Restaurants Jones recommends: 

Sites Jones recommends: 


Wisconsin’s cranberry capital is a small community. Tour a cranberry marsh and visit the Wisconsin Cranberry Discovery Center to learn about the state’s top fruit crop. Kim Schroeder is the general manager of the Warrens Cranberry Festival. This year’s event is Sept. 23-25. 

Restaurants Schroeder recommends: 

Green Bay

Green Bay is known for its NFL team, but this city also has the National Railroad Museum, Heritage Hill State Park, a botanical garden, public museum, variety of ways to enjoy the outdoors, and arts and culture. 

Sites Depenbrok recommends: 

An artist recommends: 


Minocqua is in northern Wisconsin’s lake country. Kailey Barutha is the content manager for the Let’s Minocqua Visitors Bureau + Chamber of Commerce. Its June Bloom Craft Show is June 4, with After Loon Delight on Aug. 4, and Prime Choice Craft Show set for Sept. 24. 

A restaurant Barutha recommends: 

Barutha recommends this site:


This community is in a western Wisconsin valley, located 30 minutes from the Mississippi River. Alana Back handles public relations for Ashley for the Arts, which includes an art fair, entertainment, and family fun. This year’s event is Aug. 11-13, in Arcadia. 

Back recommends this restaurant: 

A site Back recommends: 


Located along the Mississippi River, this small village has cool mornings and beautiful sunsets. Visit it for shopping, outdoor recreation, lodging, and dining. 

Back recommends this restaurant:

A site Back recommends:

La Crosse

This city on the Mississippi River has visual and performing arts venues, as well as annual festivals. There are countless opportunities to be active in the outdoors in this area. Include Grandad Bluff Park in a visit. 

Schroeder recommends this restaurant: 

Back recommends this site: 

Soldiers Grove 

Wisconsin’s Driftless Area escaped the last continental glacier. Soldiers Grove is a small community in it. Lori Bekkum is the coordinator of Soldier Grove’s Driftless Area Art Festival. This year’s event is Sept. 17-18.  She recommends visiting apple orchards in nearby Gays Mills. “Experience some of the beauty of the Driftless Area,” Bekkum said. 

Restaurants Bekkum recommends: 

Bekkum recommends this site:

Prairie du Chien

This city is Wisconsin’s second-oldest settlement and the oldest community on the upper Mississippi River. It has shopping, dining, recreation, and history. 

Restaurants Bekkum recommends: 

Bekkum recommends this site: 

More Must-Sees in Wisconsin

Wells recommends these places:

More recommendations from Depenbrok: 

Haig recommends this restaurant: 

Haig recommends this site: 

Barutha recommends this site: 

An artist recommends visiting: 

Schroeder recommends these places: 

More recommendations from Back: 

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