When thinking about road trip destinations in the US, Wisconsin might not be the first place that comes to mind. As someone who grew up in this beautiful state, I think it should be higher on your USA bucket list. Wisconsin has some incredible natural beauty, delicious cheese-laden food, and quintessential cities worth visiting. In this blog post, I hope to convince you that Wisconsin is worth visiting on a 1 week road trip. 

I lived in Wisconsin for 20 years of my life before moving to Chicago and then to Germany, so I have seen all four corners of the state. It is genuinely underrated! I am a proud cheesehead, even now that I live far away from Wisconsin. Whenever I return to visit my parents, the Sconnie nostalgia swells in me. I immediately feel drawn back to this loveable state. If you’re planning to visit America’s dairyland, I hope this detailed one week Wisconsin itinerary will be a helpful resource for planning the perfect road trip.

My Epic 7 Day Road Trip Through Wisconsin

Overview of this Wisconsin Roadtrip Itinerary

Wisconsin is a fairly large state, so there is only so much you can see on a one week road trip. I designed this itinerary to feature my favorite parts of Wisconsin and give you a taste of the state’s highlights. I hope this 7 day itinerary will inspire a return visit to see some corners of Wisconsin that I left off, such as the Apostle Islands, Rhinelander lakes district and Menomonie forest. 

As someone who lived in Wisconsin for over 20 years, I believe this itinerary is a good overview of the cheesehead state.

If you need to rent a car, I would recommend picking it up in Milwaukee or Madison, which are the two largest cities in Wisconsin. This will help keep costs down. Starting and ending in Milwaukee is a logical way to approach this itinerary. If you end in Door County as I suggest, the drive from Door County back to Milwaukee takes about three hours, so quite reasonable for your last day. 

Day 1: Milwaukee

Located on the far east side of Wisconsin along Lake Michigan lies the state’s largest city—Milwaukee. This is a smart place to begin your one week roadtrip in Wisconsin, thanks to the large airport and rental car infrastructure. Although 24 hours in Milwaukee will show you most of the highlights, there is plenty more to see if you wanted to extend your stay by a day or two. You could easily fill a whole weekend trip if you have extra time!

Start your day in Milwaukee with a visit to the Milwaukee Art Museum. Designed by famed architect Santiago Calatrava, the Milwaukee Art Museum has become the de facto symbol of the city. The stunning bird-like facade with retractable “wings” is iconic! These hydraulic powered wings open twice daily and it is something special—the first time I saw the wings open, I was absolutely amazed. They are delicate looking, but then you get up close to appreciate the true size of these massive structures.

Once inside the beauty of the Milwaukee Art Museum doesn’t stop. The interior atrium is almost as striking as the outside. The first thing you're likely to notice is the colorful installation by Dale Chihuly. There is also a dizzying array of curved white lines forming almost tunnel like hallways connecting the new section of the museum to the old. Plus, it is free to go in the atrium! There is a permanent collection as well as rotating exhibits to enjoy during your visit.

Milwaukee Art Museum Calatrava Wisconsin

Perhaps my favorite of all the Milwaukee attractions is Milwaukee Public Market. Modeled after the popular public market in Seattle, Milwaukee’s year-round indoor market is housed in a cavernous industrial-style building filled with natural light to illuminate the delightful assortment of food and dessert purveyors. Ranging from fresh fish to hand-crafted chocolates, the Public Market offers a little bit of everything. Wandering through the approximately 20 stalls is fun, and then you can sit down in the upper deck’s dining area to enjoy the view while eating.

Thanks to a government-funded large-scale redevelopment of the Milwaukee riverfront, the pedestrian-friendly riverwalk has recently connected its northern and southern branches. There is now nearly 3 miles of walkway running along the river in the heart of the city. Backing up onto apartments, parks and restaurants, I would recommend walking along at least one stretch of the riverwalk during your visit to Milwaukee. It is a beautiful and scenic part of the city!  

One of the most beloved neighborhoods in Milwaukee is the Third Ward, just south of downtown and east of the river. Once home to the warehouse district of the city, the Third Ward now sits on the pulse of the city’s food and restaurant culture, along with a variety of high-end boutiques and shops. You could spend hours window shopping in the Third Ward with local favorites like the plant & home décor focused ModGen, high-end men’s boutique Mil Works, the always Instagrammable Broadway Paper, and local shoe purveyor Shoo.

Milwaukee, Wisconsin is a city full of delicious food, beautiful architecture and unique sights to explore. This 24 hour travel guide gives you the perfect itinerary to see the best of Milwaukee in one day.

Where to Stay in Milwaukee

As a large city, there is a wide variety of hotel options available in Milwaukee. There is something to fit every budget! I can recommend a few of the more boutique and design-oriented options. My favorite hotel in Milwaukee is probably the Saint Kate. Billed as an arts hotel, this newly opened option has a fantastic location and stylish, swanky vibe. Leaning into the beer history of Milwaukee, you can spend a night at Brewhouse Inn & Suites, which is built inside the former Pabst Blue Ribbon brewery facility. Set in the heart of Milwaukee’s coolest district, the Iron House Hotel has a great restaurant and beautiful rooftop patio with sweeping views of the city.

Milwaukee Wisconsin City Architecture

Day 2 & 3: Madison

Just one hour’s drive west of Milwaukee is Wisconsin’s capital city – Madison. I lived in Madison for nearly 8 years, so it holds a special place in my heart. Madison is a must-see destination on your one week roadtrip in Wisconsin!  Coming from Milwaukee, you’ll experience how different these two cities are. I think it is important to visit both, because there is a ton of contrast between Milwaukee and Madison. Seeing the two cities back-to-back helps demonstrate the multi-faceted dynamics at play in Wisconsin. 

Madison is one of those cities that seems like one thing on the surface -- a college town, a state capitol, a Midwestern city -- but the more you dive into it, the more it defies any of those labels. Madison is a city that is quintessentially Wisconsin, but it is also unabashedly itself. This is the city that taught me how to be a foodie, so you can expect to eat well here. More than that, it was the first city that truly felt like home to me. There are lots of things to do in Madison with a 48 hour visit, including plenty of foodie and outdoor adventures. Because I lived in Madison for a while, I have several useful blog posts to help you plan a 2 day visit.

Where to Stay in Madison

There are some nice hotels to choose from around downtown Madison. Many of them are clustered around the State Capitol, for obvious reasons. The AC Hotel by Marriott is an excellent choice for those looking to splurge a bit. It has a great restaurant on the roof and numbers capitol facing rooms and suites.

A more affordable option closer to the UW-Madison campus is the Graduate Hotel. Styled with a quirky nostalgia-inducing vibe from upnorth Wisconsin, this hotel just warms my heart a bit. It actually reminds me a lot of where I got married -- Camp Wandawega. Finally, the Indigo Hotel is my personal favorite hotel in Madison. It is housed in a former paint factory with a unique decor and an industrial vibe that is rare in Madison.

Day 4: Driftless Region

Unlike some of its neighboring states in the Midwest, Wisconsin has some really interesting topographic and geologic features. There is so much more than just corn fields and dairy farms! One of the best areas of Wisconsin to see this type of natural beauty is the Driftless region. Spanning over 24,00 square miles, the Driftless region has distinctive terrain that was caused by glaciers for millions of years. Here is a great TikTok discussing the geologic history if you’re interested in learning more about how this distinct region was formed. 

Regardless, the Driftless Area is characterized by its steep cliffs and bluffs, rolling hills, and rugged river valleys. There are some beautiful limestone rock formations, amazing cave complexes, and more lakes and streams than you could visit in a lifetime. It is a truly lovely and unique place to visit in Wisconsin.

In this itinerary, I am only dedicating a day to the Driftless region, but you could easily spend several days exploring this area. A few key attractions to highlight include Devil’s Lake State Park, which is conveniently only about an hour north of Madison. This scenic area offers beautiful hiking around a deep and super clean lake. The famous Wisconsin Dells, known for the world’s largest waterpark, is only a little bit further north from Devil’s Lake. This popular family destination has LOTS of hotels, amusement parks, and entertainment options. My family would drive here frequently when I was a kid to stay for a weekend and visit the waterparks. 

If you love to see cool caves and underground formations, Cave of the Mounds is pretty incredible. Also only about an hour away from Madison by car, this cave is a popular day trip for families with guided geologic tours of the cave. Nearby is the eccentric House on the Rock, a gorgeous cliff side house with a collectors museum inside. You can also visit Taliesin, one of Frank Lloyd Wright’s architectural masterpieces, in this corner of Wisconsin. 

To venture a little bit further north, La Crosse is a small city with beautiful natural surroundings. It sits along the Mississippi River with gorgeous bluffs, a wide network of streams and marshes perfect for kayaking, and a native community of Bald Eagles ideal for bird watching. Personally, I think La Crosse has a lot to offer as a lesser known destination in Wisconsin, including some delicious food and design-oriented accommodation options. 

Where to Stay in the Driftless

If you love the outdoors, the Driftless region is a great place for camping. There are a number of state parks, including Devil’s Lake, that allow for RV’s and tent camping. Wisconsin Dells is by far the most popular place to stay in the Driftless area. For families, this is an excellent choice. Personally, I think it is super kitschy with a weird touristy feeling, but there are lots of hotels available at every price point. 

Spring Green is another popular place to stay in the area, as well as Viroqua. Of the places I mentioned above, my recommendation would be to stay at the impeccably designed Charmant Hotel in La Crosse. The entire hotel is built inside a refurbished chocolate factory with thoughtful design choices and a delicious restaurant.

Day 5: Green Bay

Set on the shores of Lake Michigan, Green Bay is Wisconsin’s oldest settlement dating all the way back to 1634 when the French established a fur-trading center here. Nowadays, it is most famous for its iconic football team, the Green Bay Packers. For many Sconnies, seeing the Packers play a home game at Lambeau field is a rite of passage. Much of the city is dedicated to the Packers, from their legacy and Titletown to themed bars and player sightings.

The recently finished and opened Titletown District is the crown jewel in Green Bay’s Packer infrastructure. This 34-acre district sits immediately west of storied Lambeau Field, and it gets incredibly lively during football season. This is the hub of tailgating and pregame antics. On a non-game day, it is a lovely new development which is easily explored on foot. There is a public park, playground, a full-size football field and lots of Packer-themed public art all around Titletown. It’s a nice area to just wander!

You’ll want to stop into the Packers Hall of Fame for a tour of franchise history. This museum is well done, telling some of the greatest stories in football history. From there, you can walk over to Lambeau for a tour of the stadium. If you want behind-the-scenes access to the locker room and press boxes, opt for the Legendary Tour  pass.

If you are interested in learning about some other parts of Green Bay history besides football, stop in at the Oneida Nation Museum, which puts the history and culture of the local Native American nation on display. Maybe you’re more interested in The Automobile Gallery. This museum features dozens of distinguished vintage cars with models spanning the last century.

Like so many other areas of Wisconsin, beer is an important part of the local culture in Green Bay. Hopping between a few different breweries is a must-do activity in Green Bay! Stillmank Brewing Company is best known for Wisco Disco, an ESB style ale brewed while Noble Roots Brewing Company offers a rotating selection of half-barrel brews.

Local Beers Madison Wisconsin

Where to Stay in Green Bay

For the true Packer’s fan experience, a stay at the Lodge Kohler in the heart of the Titletown District is a must. This high-end hotel offers state of the art plumbing facilities, courtesy of the Kohler Corporation, so you can expect amazing showers in your room. The in-house restaurant, Taverne in the Sky, offers delicious cuisine. If you need a little relaxation, schedule an appointment at Kohler Waters Spa. If you are looking for a more local or historic experience in Green Bay, the charming Astor House B&B was built in 1888 in a beautiful Victorian style.

Day 6 & 7: Door County

From Green Bay, drive one hour north towards Sturgeon Bay until you arrive in Door County, one of the most picturesque regions in all of Wisconsin. When you look at the map, Wisconsin looks a little bit like a left hand. The thumb of that hand, the Door peninsula, juts out into Lake Michigan. Door County is the Midwest’s answer to Cape Cod and a true Wisconsin gem. Beloved for its bucolic farms, dense forests, historic lighthouses, and rocky coastlines, Door County is locally known as one of the most romantic destinations in Wisconsin. 

Door County has a number of small towns on either side of the peninsula. They each have their own little flair. For your first day in Door County, go for a drive around the various towns. You can stop at antique shops, pop into tiny galleries featuring local artists, and maybe even stumble upon a fresh cherry stand on the side of the road. Driving in Door County is especially gorgeous during the fall when the trees are changing colors. 

Fish Harbor is one of my favorite towns in Door County. Feast on brunch at a local favorite, the White Gull Inn, which is famous for its stuffed cherry French toast. This is a decadent and filling breakfast. After brunch, wander around to check out small shops and art galleries. There are lots of little boutiques and gift shops, but my favorite was the Door County Vintage Candy Co. This confectionery shop is full of homemade candy and some of my childhood favorites that I forgot existed!

For your second day in Door County, get outside and enjoy the beautiful natural surroundings. You can explore Cana Island Lighthouse and the grassy dunes of Whitefish Dunes State Park on the Lake Michigan side. If you are looking for a full day trip experience, take the ferry out to the carless Washington Island. The island has some gorgeous untouched forests, as well stone beaches, quaint restaurants, and lavender farms. Maybe you want to get out on the water! You can rent kayaks, paddle boards or even small boats to experience the tranquility of Lake Michigan.  

Biking is one of my favorite pastimes, and I think it is the perfect way to experience the natural beauty of Door County. Peninsula State Park has a myriad of well-marked and well-maintained trails, perfect for an afternoon bike ride. We took the long loop around the peninsula and made several stops at lighthouses and scenic overlooks along the way. During the fall, the trees are painted in bright yellow and red colors, which makes the trails simply stunning. 

Grab a wood-fired pizza at Wild Tomato, voted one of the best restaurants in all of Door County. With an extensive beer collection to boot, this place is a great option for dinner. We ordered the Wild Pi which had chicken, feta, olives, tomatoes, fennel, caramelized onions and cheese. Plus they've got a small little patio to enjoy al-fresco dining. 

Where to Stay in Door County

Because Door County is a popular destination for couples and romantic getaways, I would recommend staying at a historic Bed and Breakfast. You’ll find them throughout Door County, and it is a charming way to support local small business owners. I can recommend the White Lace Inn in Sturgeon Bay. Built in the 1870s, this b&b has several different Victorian-style buildings on the compound as well as a lovely garden and gazebo. Our room was in the Washburn house with bright floral wallpaper and a double sided fireplace connecting the bedroom and the sitting room. Owners Dennis and Bonnie were friendly and their dog Edward was a friendly face to see at the simple and tasty breakfast. 

We have also stayed at the Scofield House. Another Victorian style mansion, this 115 year old house was fully restored to its roots. Right when you walk in there is a cherub statue and classical music to greet you. Dan, the friendly owner, gave us a tour of the home as we made our way to the Turret Suite on the second floor. With lots of lace and floral details as well as some cool antique lamps, this room made me feel comfy and cozy. The real selling point was the large private balcony overlooking the front yard.

Do you have any questions? Comment below and I can help!

Share this story

Comments Expand -
  1. Great site you have got here.. It’s difficult to find excellent writing like yours these days.
    I really appreciate people like you! Take care!!

Add your thoughts today

Your email address will not be published. Required fields are marked *