A trip through Wisconsin is the perfect blend of action-packed cities and pristine beauty. This laidback gem rolls friendly people, fantastic food, countless lakes, and of course, some of the best cheese in the country into one state, offering the best of the upper Midwest.
With a wide range of attractions and sites, Wisconsin has plenty for groups to love.
Milwaukee
There’s never a dull moment in Milwaukee. Situated on Lake Michigan, the city is packed with attractions.
“Milwaukee is Wisconsin’s largest city, and yet it remains compact and easy to navigate,” said Megan Husband, national account and tourism sales executive for Visit Milwaukee. “This makes Milwaukee ideal for groups that are looking for day trips, multiple nights, or a hub and spoke destination.”
Groups with an artsy side shouldn’t miss the Milwaukee Art Museum, which is in itself a work of epic creativity. The museum’s three buildings were designed by some of the world’s top architects: Eero Saarinen, David Kahler and Santiago Calatrava. Between exploring the museum’s collections, take a pause outside to take in the building’s beautiful “wings,” which expand across vistas of Lake Michigan.
The Milwaukee Public Museum is a great option for museum-goers who have an eye for natural history. With more than 4 million objects ranging from miniature models of ancient civilizations to life-size elephants, there’s plenty to explore.
Travelers can find great eats at Milwaukee Public Market, which features vendors offering up artisanal ingredients, fresh food and local souvenirs. With ample seating and a wide variety of cuisines for different tastes, it’s a great place for larger groups to grab lunch. To wash down the meal with a drink, groups can tour Great Lakes Distillery and Tasting Room, a local staple of nearly 20 years. A great way to wrap up a trip is with a tour of North Point Lighthouse, a gem on Milwaukee’s east side that was first built in 1855 and has been carefully restored to its historic beauty.
Madison
Wisconsin’s capital is a lively city with booming culture, delicious dining and easy access to the state’s great outdoors. As home to University of Wisconsin-Madison, it also offers the vibrant energy of a student hub, combined with the sights and scenes of a much larger city.
“What people love most about visiting Madison is we are a small city but with big city amenities,” said Rob Gard, director of communications and public affairs at Destination Madison. “It’s so well connected, accessible and walkable. We’re built on an isthmus, and we have two lakes that frame the land mass in downtown. It takes maybe 15 minutes to walk from lake to lake.” That makes for an easy stroll between museums, tours, and attractions.
State Street, the city’s main artery, is packed with shopping, restaurants and nightlife. Madison has the most restaurants per capita of any city in the U.S., so groups will have a wide array of options to choose from. Between tucking into shops, pubs and eateries on State Street, travelers will enjoy visits to some of the city’s finest art museums: the Chazen Museum of Art and the Madison Museum of Contemporary Art. The Chazen, which is located smack-dab in the middle of the charming UW campus, houses the second-largest art collection in Wisconsin. The Madison Museum of Contemporary Art features a robust schedule of programming and events alongside its collection. Admission to both museums is free.
For a relaxing foray into nature, groups will enjoy a visit to Olbrich Botanical Gardens. With 16 acres of lush greenspace, the property features a bright conservatory and several themed gardens, including the Royal Thai Pavilion and Garden, which features the only Thai Pavilion in the continental U.S.
Lake Geneva
Peaceful Lake Geneva has been a resort destination for over 100 years — and the community has continued to perfect the art of hospitality ever since.
“In the past, Lake Geneva has been coined the Hamptons of Chicago,” said Deanna Goodwin, vice president of marketing, communications and development at Visit Lake Geneva. “Lake Geneva the city, which is on Geneva Lake, became a bit of a respite for Chicagoans who after the Great Chicago Fire were looking to escape the city as they rebuilt.”
Today, the lake is dotted with beautiful historic vacation homes, many of which display breathtaking Gilded Age designs.
The lake itself spans 5,000 acres, and its 21-mile public shore path winds around its entirety. Early settlers of the area designated the land close to the shoreline as public domain, and to this day, homeowners on the lake are responsible for ensuring the shore path is publicly accessible if it crosses through their property. This makes for a fascinating blend of natural trail and unique personal design touches along the path.
Groups that want to get up close and personal with the lake will love Lake Geneva Cruise Line, which offers engaging historical boat tours and a wide range of options for groups. For a dip in the lake, travelers can stop by Williams Bay Beach.
History lovers will enjoy touring two top-notch historic sites: Yerkes Observatory and Black Point Estate. When the Yerkes Observatory opened in 1892, it was seen as a cutting-edge approach to astronomy and was operated by academics for over a century. In 2022, the observatory reopened for public tours. Black Point Estate was built in 1888 and was once the summer home of Chicago beer baron Conrad Seipp. Today, it’s an immersive historic experience with peaceful gardens.
Despite its status as a summer retreat, Lake Geneva isn’t just a warm-weather escape. Each winter, the city hosts Winterfest, which features snow sculpting contests, cozy beach bonfires, live performances and other outdoor fun.
Door County
Situated on a Lake Michigan peninsula, Doore County is famous for charming small towns and gorgeous waterfront scenery.
“Door County feels small until you get here, and then you realize how everything is so spread out and unique,” said Elizabeth Charney, marketing and sales assistant at Destination Door County. “Each town kind of has its own kind of theme and history that is so specific to that one site. No matter what you do, you’re never going to see everything in one day, which makes it really nice to be able to take and come back each time and learn.”
Door County boasts 300 miles of Lake Michigan shoreline. It’s home to five state parks and 19 county parks, and among the most popular is beautiful Cave Point County Park. The park is famous for its limestone rock formations, which tower over turquoise waters dotted with underwater caves. It’s a perfect place for a group to head out on kayaks to experience the water. Another hotspot is Washington Island, which features lush forest, beach access, historic museums, and — thanks to its rich history as a Scandinavian immigrant community — a medieval Norwegian Stavkirke church.
After basking in the great outdoors, groups will enjoy a visit to Stone’s Throw Winery, which offers tastings, garden strolls, on-site dining and bocce ball. Entertainment-loving groups can catch a performance at the Peninsula Players Theatre, the oldest resident summer theater in the U.S. With top-of-the-line performances and a beer garden to enjoy a pre-show sunset, it’s a great place to spend a summer or autumn evening.
Green Bay
Green Bay is home to a can-do community and one of the most lauded football teams in NFL history. The city has seen significant growth over the past decade, and it’s easy to see why.
“I think the growth that we’ve seen over the past 10 to 15 years has resulted in a unique destination where you can really have whatever experience you want to have,” said Nick Meisner, vice president of digital marketing and communications at Discover Green Bay. “If you’re looking for museums, art, culture, education, history — all of it, we have that. If you’re looking for outdoor recreation, you can’t find a better place than Green Bay.”
Of course, the city is also home to the legendary Green Bay Packers football team. A tour of Lambeau Field, where the Packers play, is a must. The engaging behind-the-scenes experience is fascinating, even for travelers who aren’t hardcore football fans.
“We’re known as the smallest home to a major professional sports franchise in all of professional sports,” said Meisner. “It’s more than a football team. It’s a story of how a community can come together and support something that they’re passionate about.”
Just outside of Lambeau Field is Titletown, a 42-acre mixed-use space with a sledding hill, skating rink and football field. Titletown also features dining, living entertainment and group programming like outdoor fitness classes.
For a unique local history experience, groups can visit Heritage Hill State Historical Park, an outdoor living history museum. The museum has 24 structures from the state’s history, spanning from 1762 to 1905, and offers reenactments, exhibits and workshops. Travelers will also enjoy a leisurely stroll through Green Bay Botanical Garden, which houses more than 85,000 plants and flowers across 47 acres.
