Fun and Quirky Fall Day Trips in Wisconsin

Oct 10th

Fall in Wisconsin is a season worth celebrating. Crisp air, colorful trees, and cozy sweaters make it the perfect time to plan an adventure. And if you’re living at West Madison Apartments, you’re just a short drive away from some of the most unique (and delightfully quirky) spots in the state.

Pumpkin patches and apple orchards will always have their place, but sometimes it’s fun to branch out. Here are a few nearby destinations that combine fall beauty with the unexpected.

House on the Rock – Spring Green

If Alice in Wonderland ever built a house, this would be it. House on the Rock is part museum, part maze, and entirely unforgettable. You’ll wander through rooms filled with collections that range from fascinating to downright strange. Like the world’s largest indoor carousel, complete with 269 animals and not a single horse. The drive to Spring Green in autumn is almost as memorable as the house itself, with bluffs and hillsides glowing in their seasonal colors. Weird, wonderful, and a little whimsical, this trip is unlike anything else in Wisconsin.

Devil’s Lake State Park – Baraboo

Don’t let the name fool you, Devil’s Lake is pure beauty. Towering cliffs rise dramatically above a sparkling lake, and when the leaves turn, the views are some of the best in the Midwest. Hiking here in the fall feels like stepping into a postcard. If you only have time for one trail, the East Bluff Trail is a favorite. Prefer something a little gentler? The Tumbled Rocks Trail and the Grottos Trail are both flatter, paved paths that let you soak in the scenery without the climb. Whether you’re hiking up high or strolling along the shoreline, you’ll come home with photos (and memories) that feel larger than life.

Dr. Evermor’s Forevertron – Sumpter

This is not your average sculpture park. Forevertron is the world’s largest scrap metal sculpture, created by artist Tom Every (better known as Dr. Evermor). It’s a mix of steampunk art, sci-fi imagination, and pure whimsy. Wandering through the massive structures on a crisp fall day feels like stepping into another world; one where quirky creativity reigns. Forevertron is proof that with a little imagination (and a lot of scrap metal), you can build something unforgettable. 

Cave of the Mounds – Blue Mounds

When the autumn breeze turns chilly, head underground for a change of scenery. Cave of the Mounds is a natural wonder filled with crystal formations that sparkle under soft lighting. Guided tours make it easy to explore, and the cave’s steady cool temperature makes it a perfect adventure for brisk fall days. It’s a reminder that Wisconsin’s beauty doesn’t stop at the surface; you just have to know where to look.

Wollersheim Winery & Distillery – Prairie du Sac

After a day of exploring, nothing beats winding down with a glass of local wine. Wollersheim Winery’s hillside vineyards are breathtaking in the fall, with rows of golden vines against the backdrop of the Wisconsin River. Take a tour, sip a tasting flight, and enjoy the scenery. It’s a cozy, rewarding way to cap off an autumn day. Whether you’re a wine enthusiast or simply in the mood for a relaxing afternoon, this stop blends history, beauty, and a well-deserved treat.

Your Fall Adventure Starts Here

One of the best parts of living at West Madison Apartments is how easy it is to escape into Wisconsin’s unique charm. Whether you’re in the mood for a whimsical museum, a lakeside hike, or a sip of local wine, there’s a fall day trip waiting just beyond your doorstep. So grab your favorite scarf, cue up your road trip playlist, and make this season one to remember.