The Perfect Fall Weekend Getaway in Wisconsin

As the leaves take on their vibrant hues of red, orange, and gold, it's time to make the trip to explore all Wisconsin has to offer.

 

Catie Keogh Enjoying the view at Grandad Bluff in La Crosse

 

The area surrounding the cities of Janesville, La Crosse, and Madison is perfect for a fall weekend. There you will find a blend of outdoor hiking, culinary delights, and local flair promising unforgettable memories. So, get ready to put on your coziest sweater and dive into your own picturesque autumn escape.

I started my perfect fall weekend with a visit to the impressive Skelly's Farmer's Market in Janesville. The market goes into full fall mode from Labor Day to Halloween, offering a tech-savvy corn maze, a choose-your-own-adventure wagon ride, and many other themed activities. On display were all the wonderful flavors of the season, from crisp apples to freshly baked pies and apple cider floats. Skellys Famer’s market offers an endless array of autumnal delights and Fall vibes.

A Pumpkin Bubble Waffle Dessert and Loaded Apple Cider Float from Skelly’s Farmer’s Market

Pumpkins Galore! Skelly’s Farmer’s Market

Catie Keogh at La Crosse Distillery Co

Head down the road to La Crosse Wisconsin after your farm visit and have a cozy fall evening experience at La Crosse Distillery Co. Not only was dinner amazing with fried brussel sprouts and Birra Beef Tacos, but their signature cocktails and spirits were top-notch. They even provide tours of the distillery, which can add so much to the experience

 While in the area, I recommend staying at the Hampton Inn & Suites in downtown La Crosse. It is across the street from the Oktoberfest festival grounds and the Mississippi River. It was a nice central base for the first leg of the trip.

In the morning, we headed for a leisurely hike to Grandad Bluff, one of La Crosse's most iconic natural wonders. The 600-foot-high bluff overlooks the city of La Crosse. As you ascend to the summit, the panoramic views of the Mississippi River Valley will take your breath away. There is also an option to drive to the summit as well. Don't forget your camera; the vibrant fall foliage makes for stunning photographs.

 While in the area, I recommend staying at the Hampton Inn & Suites in downtown La Crosse. It is across the street from the Oktoberfest festival grounds and the Mississippi River. It was a nice central base for the first leg of the trip.

In the morning, we headed for a leisurely hike to Grandad Bluff, one of La Crosse's most iconic natural wonders. The 600-foot-high bluff overlooks the city of La Crosse. As you ascend to the summit, the panoramic views of the Mississippi River Valley will take your breath away. There is also an option to drive to the summit as well. Don't forget your camera; the vibrant fall foliage makes for stunning photographs.

All of the walking worked up a mighty appetite, one that was easily quelled at The Breakfast Club & Pub. This place oozed 80s nostalgia, with old music videos and movies playing from the era. We had fun checking out themed menu items like The Shermer High Burger and The Farmer Ted. What a blast from the past and a great meal. 

Afterward, we indulged in some retail therapy, exploring the charming shops and boutiques of downtown La Crosse. Whether you're searching for unique fall fashion or artisanal gifts, you're sure to find treasures that capture the essence of this charming city. A few stops that stuck out were the Antique Center of La Crosse, Larson’s General, and Drift Mercantile.

While in La Crosse, don’t miss booking a relaxing sightseeing cruise aboard the La Crosse Queen. A modern-day replica of a historic steamboat, The Queen gives you a true, authentic riverboat experience as one of the few paddlewheel boats still in operation. Drift along the tranquil waters of the Mississippi River, surrounded by the fiery hues of autumn. It's the perfect way to unwind and soak in the natural beauty of the season.

Retail Therapy in La Crosse, Wisconsin

Sightseeing Cruise Aboard the La Crosse Queen

After our cruise, We drove a few hours south to Madison Wisconsin. Madison, Wisconsin's vibrant capital, is a city rich in culture and history. Consider visiting the Wisconsin State Capitol, the Chazen Museum of Art, or Tenney Park to immerse yourself in the city's roots. There is so much this town has to offer. But Madison is also known as a thriving culinary scene and lucky for us, we were hungry.

The Tipsy Cow, located in downtown Madison, met all of our expectations. Known for its “corner tavern food,” the Tipsy Cow serves bites ranging from deep-fried alligator, cheese curds, lamb tacos, and of course burgers. You can wind down from a busy day and indulge in a selection of rotating local artisanal beers here too.

The next day, We still had so much more to see and do in Madison. You can start your day with a leisurely bike tour of the city, courtesy of BCycle, the first all-electric bike share experience in the country. Explore the picturesque streets, visit iconic landmarks like the UW Arboretum or Olbrich Botanical Gardens, and get a feel for Madison's unique character.

You can also pay a visit to the Henry Vilas Zoo. This family-friendly zoo is a wonderful place to connect with wildlife, including some charming animals native to Wisconsin. Open to the public in 1911, it is one of the few remaining admission-free zoos in the country

Madison, Wisconsin, State Capital

Catie Keogh at Henry Vilas Zoo

To wrap up our trip, we took in a wonderful midday meal at Alimentari, a local gem that serves mouth-watering Italian-inspired dishes. Their seasonal selections are amazing and they produce and sell fresh pastas and sauces for you to take home for dinner.

A fall weekend getaway to Wisconsin promises a perfect blend of outdoor adventures, culinary delights, and your fill of local culture. Get ready to savor every moment of this unforgettable journey through the heart of Wisconsin. For more fall fun around Chicago and beyond, follow me on Instagram.

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