Best Road Trips of the USA: Wisconsin

Ever wanted to get a glimpse of the breathtaking natural beauty of the Midwest while enjoying delicious dairy delicacies? If so, Wisconsin is the state for you! Whether you live in the state, in a nearby location or are flying in, it’s time to chart your path around America’s Dairyland where you can experience unique towns, scenic byways and the famed Wisconsin Great River Road!

Before You Go

To get the most out of any road trip, a detailed plan is a must. Wisconsin offers water adventures during the summer, vibrant orange leaves in the fall, adrenaline inducing snow sports in the winter and the cherry blossom blooms in the spring, there is something for everyone no matter what time of year you visit.

It is important to ask yourself the following questions: “What season should I experience?” “What do I want to see?” “How long should I spend in each place?” This will help you determine what to pack, where to stay, and how long you should book stays. Once you have answered these questions, and any others that might be important during the planning phase, it is time to set off on your epic journey!

If you are looking for insights into some of Wisconsin’s must-see locales and experiences, check out these exciting destinations.

Milwaukee

Milwaukee is the perfect place to begin your Dairyland drive. Located in southeast Wisconsin on the border of Lake Michigan, this confluence of art, culture, cuisine and Harley’s is full of things to do, especially if you have a festive personality.

There is always a party happening somewhere in the City of Festivals. If you are into tasty brews, consider planning your visit around the Weird Fest. If music is your passion, then Summerfest might be more your speed. If you just like to party and are okay going with the flow, then check out Milwaukee's Festival Calendar. With over 100 festivals to choose from, you are certain to find something to enjoy.

If you prefer a more relaxed pace, check out the amazing educational experiences that Milwaukee has to offer.

• Milwaukee Public Museum – Explore the history of Ancient Civilizations, learn about prehistoric creatures, take in the beauty of the butterfly garden or experience Old Milwaukee at the Milwaukee Public Museum.
• Discovery World – Observe marine life in the aquarium. Expose your kids to the power of flight and the intense speeds of racing in the flight and race simulators. This blend of education and entertainment makes Discovery World a perfect excursion for the whole family. 
• The Mitchell Park Horticulture and Conservatory (The Domes) – This unique walkthrough experience allows guests to navigate a variety of biomes, each designed to replicate specific climates. Avoid cacti as you trek through the desert, surround yourself with over 1,200 plant species in the tropical rainforest and embrace the beauty of the floral gardens.  It is a globetrotting adventure that you can experience in a day.
• The Harley Davidson Museum – Milwaukee is the birthplace of the Harley-Davidson motorcycle and home to the only Harley-Davidson Museum in the world. The 20-acre campus houses over 450 motorcycles, interactive exhibits and a plethora of historical information about the legendary motorcycle manufacturer. After your visit you may even be inclined to swap your rental car for a motorcycle.

• Lake Michigan – If you are interested in soaking up the sun or relaxing in the water, then Lake Michigan is the place to be. Located at the intersection of three rivers, this great lake is full of activities for aquatic enthusiasts. Urban kayaking, floating taverns, boat tours and surfing are just a few ways to spend your day.

• Kettle Moraine State Forest  – Whether you go north or south when departing Milwaukee, the Kettle Morain State Forest should not be missed. If you choose to head to Green Bay next, then the best opportunity to see the state forest is to stop at the northern unit located 57 miles northwest of Milwaukee. The geology of Kettle Moraine is believed to have been molded and shaped by glacial activity. All the bogs, kames, marshes, bluffs and other landscape formations are believed to be the remnants of the most recent ice age. This resulted in parts of the forest being included in the Ice Age National Scientific Reserve.  One of the best ways to observe this majestic arboreal wonder is by taking a 115-mile scenic drive.

Highlights include:

• The Kettle Moraine Red Oaks
• Johnson Hill Kame
• Spruce Lake Bog
• Butler Lake Flynn’s Spring
• Dundee Kame
• Kettle Hole Woods
• Haskell Noyes Woods
• The Wade House
• The Holy Hill
• Cushing Memorial Park
• Old World Wisconsin

If you are interested in spending some extra time exploring the forest, camping, fishing and hunting are all available. Permits and licenses are required to participate in these activities. Be sure to research the requirements before you go.

Green Bay

Continue north through the forest for 93 miles, and you will find yourself in Green Bay. Home of the first ever Super Bowl winners, the Green Bay Packers. In fact, Green Bay’s nickname Titletown is a reference to the football team’s 12 NFL titles. Though football is big in this town, there is much more to it than cheeseheads and pigskins.

Did you know that Green Bay is home to waterfalls? The Niagara Escarpment, the same geological formation that the Niagara Falls flows from, stretches all the way from Buffalo to northern Wisconsin creating several stunning smaller scale waterfalls for Wisconsin visitors to enjoy. Both Fonferek’s Glen County Park and Wequiock Falls County Park offer stunning views of these natural wonders. If you visit the latter during the wintertime, you will be privy to beautiful ice formations.

When you are done exploring the falls, venture into the past in one of Green Bay’s museums. We’ve highlighted two of the standouts, but there are several more in the area if you find yourself craving more historical facts.

The National Railroad Museum – Here, you will learn about the history of railroads through educational programs and interactive exhibits. If you happen to be visiting between May and September or on weekends in October, the museum offers a $5.00 train ride. This informative 25-minute journey is meant to educate guests on railroad safety, hobo culture and rolling stock.

Packers Hall of Fame – If you cannot get enough football, then this is the place for you.  The Hall of Fame is dedicated to the Packers and their impact on the sports world. It is a tribute to their success and an educational opportunity that allows guests to immerse themselves in the history of the first Lombardi Trophy winners from the early years to now.

For those looking for additional outdoor activities, Green Bay offers several hiking trails and fishing opportunities for visitors to enjoy. If you are seeking something outside, but a little less wild, then you might want to check out the Green Bay Botanical Gardens or NEW Zoo.

Bayfield

Located on the border of Lake Superior just 279 miles northwest of Green Bay is “The Best Little Town in the Midwest,” Bayfield. This quaint town is known as the gateway to the Apostle Islands of Lake Superior. 21 islands make up the Apostle Islands National Lakeshore. Visitors can reach them by ferry or by personal watercraft.

Explorers can venture from island to island via sea kayaks and stay in primitive camp sites as they explore. When on land, take advantage of the hiking trails that run the lengths of the islands. In your travels, be on the lookout for the sea caves that riddle the shorelines. During spring through fall, these can be seen via the Lakeshore Hiking Trail or by taking a boat or kayak tour. 

During the winter, the best opportunity to experience the caves is by hiking the Apostle Meyers Beach Landing. Getting to the caves during this time of year depends on the ice being safe enough to cross. If you are fortunate to cross the ice, you may even experience the ice caves that form on rare occasions. 

Devil’s Island Lighthouse at Apostle Islands

While you are in the area, stop into one of the visitor’s centers to learn about the Ojibwe. This people group is believed to be the first group of people to have settled in the area. To survive, they traveled throughout the islands gathering supplies and bringing them back to their primary village on Madeline Island.

Prescott

When you have finished island hopping and hiking in the Apostles, it is time to head 207 miles southwest to Prescott. This historic city that lies at the junction of the St. Croix and Mississippi Rivers was founded in 1839 and is considered one of the oldest Wisconsin towns on the Mississippi. This small town was once a hub for commerce, milling, steamboat traffic and shipping due to its strategic location and access to these two major rivers. However, the advent of the railroads, and the exhaustion of lumber resources changed all of that.

Standout stops include:

Freedom Park Great River Road Visitor and Learning Center – This is the number one thing to do in Prescott. Named “Freedom” after the recovered bald eagle that was released there, this 4-acre park is home to birds of prey, Mississippi overlooks, prairie and butterfly gardens, a waterfall and an educational center that covers topics like logging, steamboats, clamming, eagles and more. There is always something to see and learn.

The Orange Dragon Art Gallery – Visitors are in for a treat when they stop into this art exhibition. This non-profit art gallery proudly exhibits the works of local artists. It is considered a non-juried space, which means all artists are allowed to showcase their work.

The Welcome and Heritage Center – This is the one stop shop to get a more detailed understanding of Prescott’s history and information on local attractions. Constructed in 1885, this building was once the home of the town’s first newspaper and the H.S. Miller Bank.

Great River Road

When departing Prescott for Prairie du Chien, consider road-tripping down Wisconsin’s National Scenic Byway, the Great River Road. This famous byway is nearly 250 miles in length and passes through over 33 historic towns as it chases the rushing waters of the Mississippi River.

This beautiful drive offers so much for visitors to experience. Painters, photographers, birdwatchers and those who appreciate good views will have no shortage of them. The byway is dotted with several scenic overlooks where drivers can stop and take in the view.

Some of the most picturesque vantage points include:

Brady’s Bluff – This bluff sits around 460 feet above the Mississippi River and offers magnificent views of Trempealeau Mountain.

Grandad Bluff at La Crosse – From this vantage point, you will be treated to a spectacular view of three different states: Wisconsin, Minnesota and Iowa.

Old Settlers at Stoddard – This remote stop promises privacy, relaxation and a clear view of the night sky that stargazers will love. The trails are all paved and easy to navigate. It takes roughly 25 minutes to complete the hike.

With all the historic sites, outdoor adventures and scenery to take in, be sure to leave some time for discovery. The last thing you want to do is miss something special by rushing to your next destination.

Prairie du Chien

Just 175 miles south of Prescott is the town of Prairie du Chien. This small town located on the Upper Mississippi was established as an early Euro-American settlement that thrived on trade and commerce. In recent years, the downtown district was overhauled to be a hub for economic and social development.

The town’s leadership has worked to keep the soul of the town alive through architectural restoration, period streetlights, updated landscaping and new streetscapes. The town is filled with venues that make space for community events like movie nights, street music and farmer’s markets. This lively, welcoming locale is the perfect pit stop for community and fun.

When you are not hanging out with the locals, be sure to stop in at the historic sites. The most notable in the area being Villa Louis:

Villa Louis Historic Site – This 25-acre landmark offers insight into Wisconsin’s second oldest city and the Wisconsin Dynasty that resided there. The property is home to the Brisbois House, an old fur trader’s home, and the Astor Fure Warehouse which has been converted into a museum. Additionally, the remnants of Fort Crawford, the site of Wisconsin’s only battlefield in the War of 1812, are on the property.

If you visit the weekend after Labor Day, you will not want to miss the annual Villa Louis Carriage Classic which features competitive carriage racing in honor of the standardbred-training facility that used to exist on the Villa’s grounds.

Spring Green

After you have had your fill of the fur trade and carriage races, head 65 miles east to the quaint village of Spring Green. Spring Green is a small town with a massive reputation thanks to famed resident and renowned architect Frank Lloyd Wright. While you are in town there are plenty of opportunities for more outdoor exploration, historical touring, artistic admiration and retail therapy.

Here are some of the staples of Spring Green:

The Driftless Region – The unique region spans 24,203 square miles and is referred to as the driftless region because it went untouched by the last continental glacier drift. The region contains the largest concentration of cold-water streams in the world and is home to waterfowl, fish, and a wide array of animals. The most popular ways to experience the area are canoeing or camping.

Taliesin – The name Taliesin, which is Welsh for “shining brow,” is the name of Frank Lloyd Wright’s architectural wonder of a home. It received this name because it was built on the “brow” of a hill in the Driftless region. This limestone home was built on top of Wright’s favorite boyhood hill in the valley that his family owned. Sign up for a tour of the estate where you will learn about the three iterations of the home, Wright’s legacy, and the Wright Foundation’s preservation efforts.

American Players Theatre – The theatre is a spectacular locale nestled in the middle of 110 acres of woods and meadows. The space is equipped with two theatres that offer very different experiences. The hallmark of this exceptional performance environment is the newly renovated outdoor amphitheater that is capable of seating 1,075 theater patrons. The theater produces nine plays annually and welcomes over a 100,000 guests per year (American Players Theatre Repertory | Travel Wisconsin). If there is a show that coincides with your visit, you will not want to miss it.

Madison

33.4 miles east of Spring Green is the state’s capital, Madison. With five lakes and over 200 public parks, there is always something to do while you are in the city. In fact, the city boasts having all the fun of northern Wisconsin while also having the benefits of city life. Recreational activities, culinary experiences and educational opportunities abound here.

Outdoor Activities – Madison may be a big city, but it is still home to several phenomenal recreational activities like Platinum-level bike trails, kayaking and miles of hiking trails.

Dining Experiences – Madison’s culinary culture cannot be missed. Its supper clubs have been featured on Top Chef and in the New York Times’ 2022 America’s Best Restaurants and received 42 James Beard award honors. Standouts include: The Harvey House, Driftless Social, L’Etoile, Tornado Steakhouse, Lola’s Hi-lo Lounge.

Museums – The city is home to several museums where the entire family can participate in interactive educational experiences and peruse the expansive exhibits.

• Madison Children’s Museum
• Madison Museum of Contemporary Art
• National Mustard Museum

Monroe

Located 45 miles south of Madison and 111 miles west of Milwaukee is “Cheese City USA,” Monroe, Wisconsin. This is the place to find out why the residents of Wisconsin are referred to as cheeseheads. To make the most out of your visit, be sure to visit during an even-numbered year so that you get the chance to experience the biennial celebration of all things cheese and dairy known as Cheese Days.

The festival includes traditional Swiss-Germanic music such as polkas and waltzes, carnival rides, local foods and, of course, a diverse assortment of cheeses. The grand finale of the event is a two-hour parade. 100,000+ people participate in the celebration over a three-day period.

During odd years, you can still get your fill of cheese by exploring the National Historic Cheesemaking Center. This museum is the only one of its kind and is home to a restored cheese factory. Visitors can immerse themselves in 180 years of cheesemaking history.

Traveling to Wisconsin? AAA Saves You Time & Money

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