Wisconsin Itinerary: Southern Wisconsin Crossroads

Activities, Midwestern US Itinerary

This four-day/three-night tour of the southern Wisconsin Crossroads region gives groups a taste of small town history and culture.

3 Unique Experience on This Trip

  • Fireside Dinner Theatre
  • Mount Horeb
  • The House on the Rock

Duration: 4 Days

Available: Year-round

This Itinerary is Ideal For: All

Itinerary Details

Day 1

Beloit, Janesville and Fort Atkinson

As your Wisconsin adventure begins, your first stop is in Beloit, one of the state’s southernmost cities. EnjoyVisit Beloit Southern Wisconsin Crossroads a charming Wisconsin supper club, a new-age burger joint and the Historic Auto Attractions museum just across the border in Rockford. Make a stop at one of the only working gristmills in the state. Known as “Wisconsin’s Park Place,” your next stop is in Janesville. A popular themed itinerary is the Blooms, Brews & Arts tour. There’s a self-guided walking tour of downtown and a guide to the barn quilts in the area.

Travel to Fort Atkinson, located along the Rock River. Explore a historical museum and dairy farm retail store. The town offers a variety of dining opportunities such as an Irish pub and sandwich shop. For one of the most popular group dining experiences, make plans to stop at the Fireside Dinner Theatre. From a personal greeting and escort to the many beautiful dining rooms to the over-the-top gift shop, your group will be entertained even before the main show. Then enjoy a Broadway-quality show in an intimate theater-in-the-round.

Day 2

Stoughton, Mount Horeb and Middleton

Your day begins with a short drive to Stoughton to learn about its Norwegian heritage and early immigrants. This quaint town incudes a museum, tobacco farm, Victorian architecture and a second-story opera house. Head west to Mount Horeb, known as the “Troll Capital of the World.” Rich in Norwegian history, the town features the Trollway with shops, galleries and restaurants. Be sure to have a group picture taken with these winsome characters.

On to Middleton, which is just minutes from the state’s capital: Madison. Local attractions include a brewery, mustard museum and fantastic shopping. This is a great hub & spoke location for your urban experience in the area. Located between two lakes, it blends politics with art, sports with academia.

Day 3

Spring Green and Baraboo

Prepare to be entertained and amazed at The House on the Rock, built atop a chimney of rock. This collection of collections includes the world’s largest carousel, automated music machines, a transportation building, an ice cream parlor, a Santa display during the holidays and, of course, the house that Alex Jordan built.

If your group is traveling in the summer months, be sure to include a trip to Baraboo in your tour. That’s when the greatest show on earth comes to town to celebrate the Ringling Bros. and Barnum & Bailey Circus at Baraboo’s Big Top Parade & Circus Celebration. Featuring a grand marshal, 75 traditional circus parade units, a concert, carnival games, food vendors and live performances, this one-of-a-kind festival is a must in your Wisconsin plans.

Day 4


As you leave the state, make a stop in the heart of southern Wisconsin cheese country at the Alp & DellAlp & Dell Cheese Store Southern Wisconsin Crossroads Cheese Store in Monroe. Shop for cheese curds, nine varieties of Swiss cheese, medium-to-aged cheddar cheese, five different types of Farmer’s cheese and a variety of summer sausage and imported cheeses. As their saying goes: “Eat cheese and live well.”

Contact Dairy State Tours to plan your next trip to southern Wisconsin. This receptive tour operator offers packaged agricultural tours, Frank Lloyd Wright experiences and customized itineraries of Wisconsin attractions, hotels and restaurants.

For more group travel planning advice and inspiration in Wisconsin, download the Circle Wisconsin Tour Planner.


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