Take a Wine and Cheese Tour Through Wisconsin’s Best Vineyards and Cheesemongers

Jul 25, 2025

It’s National Wine and Cheese Day, and we’ve got good news: You don’t have to travel all the way to California or Italy or France to enjoy some of the world’s finest wines! That’s right, our neighbour to the north, Wisconsin, is home to more than 100 commercial wineries and 5 different wine regions. In addition, Wisconsin is also known as the Cheese capital of the world, and for good reason: cheesemakers here are credited with crafting six hundred different cheese varieties in more than 125 cheese plants and dairy shops, and sourced from the nearly 10,000 dairy farms in state. Today’s post is all about fantastic cheesemongers and vineyards of Wisconsin, and each of them would make a great “wine crawl weekend” with your loved ones**

And of course, what goes better with these handcrafted cheeses than an incredible wine? That’s right! Wisconsin is not just Cheese Central, but it’s also an iconic destination for wine enthusiasts. On today’s blog, we’re taking you all around “Wisconsin Wine Country” as we explore some of the region’s best wineries, as well as unique cheese and dairy makers that you simply must sample along with your fine wines!

Without further ado, we present to you an alphabetical list of incredible wineries and cheesemongers you simply must visit when you’re in Wisconsin:

Aeppeltreow Winery in Burlington WI produces small batch cider, perry (a pear cider), and speciality spirits and bespoke wine. They offer picnic flights or tasting flights with your choice of beverages from their seasonal menu (the dessert wines are of special note here!) Learn about their special cultivations of cider apples and perry pears, and the difference between American and European grown fruits.
Bailey’s Run Vineyard and Winery in New Glarus offers live music, beautiful sunset views of the vineyards, specialty food pairings, wine flights, and is open 7 days a week for your enjoyment.
Baraboo Bluff Winery in Baraboo offers lush, sprawling views of the winery at its outdoor picnic areas and wine tasting events. You can even bring your well-mannered, leashed pets to visit with you! There are three indoor tasting rooms, three bars with indoor seating, and a retail store on site. Plus, plenty of room to bring your own picnic and enjoy a wine flight with lunch. Special events include live music, tours of the vineyard, and more.
Baumgartner’s Cheese Store & Tavern in Monroe has indoor and outdoor seating soyou can enjoy some fine local Wisconsin cheese and sample the local wine and spirits! If you’re looking for a full meal, you can check out the custom menu featuring both local and imported cheese on homemade sandwiches, burgers, and salads. A taste of the Swiss Alps right in the heart of Wisconsin!
Brambleberry Winery is one-stop shopping if you’re looking for a romantic getaway for couples. This winery is nestled on the grounds of a gorgeous country estate, with luxury accommodations, a medieval themed tasting room, and a speciality Reiki healing suite.
Carr Valley Cheese in Sauk City prides itself on its World Famous cheddar cheese curds, made fresh daily! The Cook Family’s locally owned and operated dairy farm is nestled in the rolling emerald hills of central Wisconsin, and churns out some of the most incredibly fresh and sharp cheese you’ll simply die for!
Cedar Creek Winery is perfect for your end of summer/early fall getaways with their annual Wine and Harvest Fest. Not only will you get to sample their incredible wine selection, but it also includes local artisans and vendors, top notch food and beverage, and live music on the main stage.
Cedar Grove Cheese in Plain is a specialty organic cheese maker offering both artisan special cheeses and local traditional cheeses using cow, sheep, and goats milk from local farms.
Chateau St. Croix Winery in St Croix Falls is modeled after a traditional French Chateau to give you a cozy yet elevated tasting experience. Wine tasting flights will allow you to sample 5 different offerings. It’s also dog friendly provided your pup is on a leash and well-mannered.
Door 44 Winery in Sturgeon Bay is situated right in the heart of Door County, making it a must-visit destination on your trip! The winery uses locally grown, award winning grape wines at its state of the art facilities. Enjoy an afternoon of wine-tasting or stop by for their special pop-up events with local food vendors and markets to shop.
Fromagination in Madison is located at Capitol Square in the heart of “America’s Dairyland”. Here, you can learn all about the local history and process of cheese making at their special classes such as “Create a Cheese Board” or “Wine and Cheese Pairings” or “Create an Authentic Fondue Meal” to stretch your culinary expertise. Or you can opt to sample the wide array of delectable cheeses to pair with your local winery bottles.
Pieper Porch Winery in Waukesha offers paid wine tastings on the winery porch or in the vineyard, and set against a scenic backdrop of the Vernon Marsh. Visitors report that it’s a great picnic setting for a BYO lunch to pair with the wines and take some scenic photographs. It’s a laid back, serene atmosphere and the perfect place to unwind. Summertime is prime season for special events and their trademark “wine slushies.”
Widmer’s Cheese Cellars in Theresa has been a staple in the local community since 1922, and it’s easy to see why. The reputation of their prize winning local Wisconsin Cheddar has made them a family favorite! This family-run operation has been a fixture in the local dairy industry for decades, and Joe Widmer is officially 1 of only 8 certified Wisconsin Master Cheesemakers in America. Their cheeses are crafted only in small batches, and the curd is moved by hand from the vats to the molds for a unique taste you won’t find anywhere else.
Wisconsin Cheese Mart in Milwaukee offers more than 150 varieties of local Wisconsin cheeses! Locals recommend sampling the horseradish cheese, unusual options like the “chocolate fudge cheese”, the 5-year aged cheddar, morel and leek monterey cheese, Marieke gouda, and white cheddar with cranberries for starters. There’s so many varieties to choose from, you’ll find plentiful options for pairing with your favorite Wisconsin wines.
Wollersheim Winery and Distillery is a sprawling 30 acre vineyard and retreat in Prairie du Sac. It’s been in the business since the 1800s! We highly recommend opting in to the guided tour which includes a full experience of this hillside vineyard, and ends in an exquisite wine tasting featuring award winning wines. Grab a bite to eat at the end of your tour at the on-site Bistro for some delectable treats, too!

**A gentle reminder: Classic really cares about our clients and customers, and we just want to take this opportunity to remind you to always drink responsibly and drive sober. When you’re enjoying your way through the many vineyards and wineries of Wisconsin, always make sure you’re doing so responsibly. Assign a designated driver to your party, join a local wine country tour, or schedule a rideshare service to pick you up so you can get to your destination safe and sound.