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Our Wisconsin Road Trip with Lands’ End Heritage Tour

Our Wisconsin Road Trip with Lands’ End Heritage Tour

If you have been following us for a while you might know we are from Wisconsin, even if you are not sure you could point it out on a map. Sometimes the Midwest is overlooked as a tourist destination. People either opt for a trip to either coast or out west – but those who come, know there’s a lot of good times to be had here.

We teamed up with Lands’ End to show you some of our favorite spots in the state!

The Lands’ End Heritage Tour

Lands’ End let us borrow their sweet Airstream trailer to drive around the state for two weeks. We did two separate road trips in Wisconsin, one in the Southern Central part of the state and on in Northern Wisconsin. Both trips were a lot of fun and brought us to both new places and places we grew up with and love visiting.

Being a Wisconsin based company, Lands’ End wanted us, Wisconsin based travel bloggers, to show you guys the beauty of our state. When most people think of Wisconsin they think of just a few things: Cheeseheads, beer, and probably more cheese. While we aren’t going to deny our love of cheese and beer, there’s a big state filled with a lot of interesting sights and things to do.

The Airstream

Before we get into the details of where we all went on our Wisconsin road trip let us introduce you to our bright blue Airstream that we lived in for a few weeks this fall. The first thing you might notice is that it is bright blue. Secondly, there is a handle on top. The Airstream was custom made to look like the Lands’ End Seagoing Duffel, one of the brand’s signature items.

The inside of the Airstream was decked out top to bottom with Lands’ End gear and home goods. Inside the closets as you might have guess, Lands’ End Fall Heritage Collection clothes. On all our adventures we’ll be wearing gear from the Heritage Collection that fit right in with our fall travels.

Adam: All-Season Flannel Shirt –  Hannah: Down Vest

Camp Life

We have camped all around the world from Arizona to Africa, but this was our first time in a travel trailer. There were a few things to get used to, but it was a sure a lot more comfortable than our minivan camper van we toured the Us in! Outside of our Airstream, we decorated with lights and some seasonal flare. Even though we saw some amazing things while touring around Wisconsin, some of our favorite memories were from the campsite just sitting around the fire.

Wearing: Drifter Cotton Crewneck Sweater, Pull-On Skinny Jeans, and Buckle Driving Mocs

Central Wisconsin Road Trip

Our first week of the Lands’ End Heritage Tour we focused our road trip around the central part of the state which has some of Wisconsin’s top tourist attractions. This part of the state we hadn’t spent a lot of time in before this trip and we found a lot of fun things to see and explore.

Adam: Squall Jacket – Hannah: Squall Rain Jacket

Governor Dodge State Park

Our first stop was right in the backyard of Lands’ End in Dodgeville, Wisconsin at Governor Dodge State Park. We setup up the Airstream and made camp for our first week of the Heritage Tour. Inside the park are a few quiet lakes surrounded by trees and tall cliffs – perfect for an afternoon kayak.

Hannah: Hooded Poncho

House on the Rock

If you find yourself anywhere near Spring Green on a Wisconsin Road Trip you really need to make your way over to the House on the Rock. By the name, you might just think it’s a famous house that happens to be built on a rock, which it is – but it’s more than that.

The crown jewel of the property is the glasshouse perched precariously on the top of an outcropping of rocks, but once you’re inside you’ll quickly realize there’s a lot more to see. It’s a collection of collections of interesting retro randomness from Asian art to classic cars to vintage animatronics. The collections have far outgrown the house and now fill large exhibit halls divided into themes that take you on a bizarre journey for the senses.

The world’s largest Carousel

One of our favorite exhibits was toward the end of the second section of the House on the Rock called the Carousel Room. Here you’ll find the largest and probably the most expensive antique carousel on earth. Hundreds of carousel horses and figurines of all shapes and sizes fill this massive room while the carousel spins holding even more figurines.

When we left the House on the Rock we both kind of looked at each other and said ‘I don’t know what I just saw, but I liked it’.

Adam: Comfort First Shirt with Cool Max – Hannah: Denim Jacket

Taliesin Frank Lloyd Wright House

Architecture buffs will not want to miss the Frank Lloyd Wright (FLW) homestead built into the hills around Spring Green Wisconsin, named Taliesin. Here FLW lived along with a group of students and mentors. The house and gardens are now preserved by a small group of staff and volunteers. The home is still an active campus for architectural learning. What makes this house special besides its famous resident is the design principals used here that were so important in Wright’s building designs. The beautiful building has a very harmonious relationship with the land and natural elements that surround it.

We visited on an evening tour where we sipped wine as we wandered the grounds and nicely kept gardens at Taliesin.

The National Beer Museum

Well, it wouldn’t be Wisconsin without some beer and one of our favorite Wisconsin Breweries is in the tiny town of Potosi. Located not too far away from the banks of the Mississippi River in southwestern Wisconsin is not only the Potosi Brewery but also the National Brewery Museum. Inside the museum, you’ll find brewing memorabilia and antique beer marketing items like old school neon signs and cans from a time gone by.

This was a fun place to spend an afternoon and sip on some great beers.


Another highlight of our time in the southern part of the state was nowhere else but the capital city of Madison. Our trip to Madison overlapped with the annual food festival called “The Taste of Madison”. In true Wisconsin fashion, there was no shortage of cheese. Some of our favorites were the famous cheese curds from the Curd Girl food truck and the mac n’ cheese.

Even outside the Taste of Madison, the city has a great culinary scene with everything from the classics to the modern. A few fixtures in the city not to miss are the Tornado Club a classic Wisconsin supper club serving up nice steaks and The Old Fashioned for a one of Wisconsin’s unofficial state drink the Brandy Old Fashioned.

Hannah: Denim Jacket and Straight Leg Colorful Jeans

In the afternoon we had the chance to jump on a boat with the guys from Clean Lakes Alliance and learn a little bit about the lakes and a few different sustainability programs that are supported by Lands’ End. The lakes in Madison are such an important part of the city, it’s good to see people taking an active role in making sure they are healthy.

Wearing Tuxedo Bib Shirt Dress

In the evening we grabbed a table at the rooftop patio restaurant at the AC hotel just in time for sunset. From high above Madison, we had unbeatable views of the capital and Lake Mendota. This is now our new goto place while in Madison, just be sure to get here a little bit before sunset in the summertime because it does fill up outside on the rooftop patio.

Wearing: Down Vest, Pull-On Skinny Jeans, and Long Sleeve Shirt

The Mustard Museum

Another quirky stop on a Wisconsin road trip is the Middle Mustard Museum. The museum sprouted from what was once a very robust personal collection of mustard that grew into a full-on museum housing jars of the yellow stuff from around the globe. There are over 6,000 jars/bottles of mustard!

Wearing: Down Vest, Pull On Skinny Jeans, and Long Sleeve Shirt

A Trip to the Farm

Another distinctly midwestern thing to do is to visit a local farm and farmers market for fresh produce and maybe a candy apple. We visited Eugster’s Farm Market near Madison from a friend’s suggestion and it turned out to be a fun little stop with some nice photo spots!


Wisconsin Dells

On our way to Northern Wisconsin for our second week of the heritage tour, we made a stop at one of the state’s most popular tourist destinations, the Wisconsin Dells. We both grew up spending time here as kids, usually in the summer though. It was nice to see it in the fall, we were a little bit early for the colors in the southern part of the state, but a few of the trees had started to turn and the temperatures were still pretty nice.

Wisconsin Dells - Wisconsin Road Trip Stops

Wisconsin Dells Boat Tour

The main tourist draw for the Dells are the waterparks, however, it wasn’t exactly swimsuit weather when we visited – which was fine with us. We were here for the natural beauty of the area and some early fall colors. One thing you have to do when you come to Wisconsin Dells is to take a Wisconsin Duck’s boat cruise. We opted for a tour of the Upper Dells that hold some of the most interesting rock formations and unique scenery.

Wearing: Squall Rain Jacket and Curvy Skinny Jeans

Witches Gulch

The highlight of our tour of the Wisconsin Dells was the Witches Gulch which is a narrow canyon with tall walls of smooth sweeping rocks. The natural formation was formed by the waters of the Wisconsin River eroding it away leaving behind spectacular narrow rock canyon.

Wearing: Down Vest, Heritage Flannel, and Knit High Waist Leggings

Stand Rock

Another highlight of the boat tour was the impossible-looking Stand Rock another oddly shaped leftover from the river’s ability to carve out the landscape. The top piece of rock perched at the top of Stand Rock sit just under 50 feet above the ground that it seems to shoot right out of. The Dells and this unique rock area definitely worthy of a place on your next Wisconsin road trip itinerary.

Adam: Heritage flannel, Jeans, Down Vest, and Chukka Boots – Hannah: Wearing: Down Vest, Heritage Flannel, Lands’ End lined duck boots, and Curvy Skinny Jeans

Northern Wisconsin Road Trip

In Wisconsin, we love our traditions, and one of our favorites is heading ‘Up North’ – it’s something we both did as kids and still enjoy. Just about every Wisconsinite uses the term ‘Up North’. Everyone’s actual destination is slightly different, but ‘Up North’ is more than a location, it’s a place where memories are made.

Around a campfire, or out on a lake – these are the things we grew up doing, and things we’ll never grow out of. Our second trip in the Lands’ End Airstream focused on a part of the state that is very special to us. Our ‘Up North’ is near the Town of Lake Tomahawk. This area is where Hannah’s family spent summers by the lake and still have a cabin in the woods here. 

Indian Mound State Campground

Our base for our Northern Wisconsin road trip was right on the shores of the lake that bears the same name as the town, Lake Tomahawk. We scored a lakefront campsite right in the peak of the autumn colors in Northern Wisconsin. We surprisingly had just about the whole campground to ourselves. Our campsite was surrounded by colors, we had just about every shade of fall right outside the steps of the airstream. We really couldn’t have found a better campsite.

Wearing: Heritage Flannel

Fall Colors

The highlight of our time in Northern Wisconsin was definitely all of the fall colors. We got lucky with our timing and we ended up with probably the best week as far as colors go. The trees were on fire with oranges, reds, and yellows. A few days we just set out to go down every road we could find looking for quiet lakes surrounded by colorful trees.

Wearing: Waterproof Rain Jacket

The weather was a different story, most of our week up north was under a rain cloud that brought on a flood watch for most of the week. Despite the raindrops trying to slow us down we still made the most of our time with our Lands’ End rain gear. We had to change our plans a few times, but some of the stops we made because of the rain ended up being some of our favorites.

Adam: Heritage flannel, Jeans, Down Vest, and Chukka Boots – Hannah: Wearing: Down Vest, Heritage Flannel, Lands’ End lined duck boots, and Curvy Skinny Jeans

One of our favorite stops was to a lake that has always been a place we’d spend a lot of time on while up north, Hasbrook Lake. One morning we came down to the lake and found it absolutely still and the reflections were so still it looked like a mirror.

Copper Falls State Park

Way up here in Northern Wisconsin, the Bad River carved tall canyons into the landscape over millions of years leaving behind some of the state’s most impressive waterfalls. On a rainy day, we took the trip from our campground up to the park. We found a handful of nice waterfalls surrounded by vibrant fall colors.

Adam: Heritage flannel, Jeans, and Down Vest

There were several impressive sets of falls, but one of the best was the one that shares the name with the park, Copper Falls. Here two side by side streams of water gushed from all the recent rains leaving behind a mist as it splashed down into the river below.

For more pictures of our time on the Lands’ End Heritage Tour and in the Airstream be sure to check out Lands’ End Instagram account.

*This trip was in collaboration with Lands’ End but all thoughts & opinions are our own. 

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Blue Airstream driving through fall colors on a Wisconsin Road Trip - pin for Lands End Heritage Tour