pouring glass

Photo by Taisiia Shestopal

Touring the Driftless Region’s wineries and breweries can be a great way to spend a Saturday or Sunday, especially during the summer and fall months. Travelers can get to know the friendly people of the Driftless Region, support local communities and businesses, and enjoy the scenic drives from one place to the next. There is much to see and do, you may decide to split this itinerary into two days.

Each establishment will also greet visitors with unique drink and food menus, fun atmospheres, and often exciting events. To safely enjoy these attractions and fully enjoy the day, be sure to always travel with a designated driver and drink responsibly. If you would like to extend your trip to a full weekend of breweries and wineries, check out this full list of Driftless Region wineries and breweries, and these accommodation options. Business hours may shift from day to day, so be sure to look up when each location is open and on which days.

bar Driftless

Photo by Meritt Thomas


Start your day off with a late morning in Westby, WI, a small Driftless city with a strong Norwegian heritage. Here you can fill up on a hearty breakfast and coffee at Borgens Cafe to energize you for the day and ensure you’ve had a meal before heading to the wineries and breweries. If you like pancakes, many recommend the Great American Pancakes & Borgens Cafe Cinnamon Bread French Toast.

Since many of the wineries and breweries do not open until after 11am, you can use this time to take a scenic drive to Hillsboro, WI by heading up through Cashton and taking Highway 33 through Wildcat Mountain State Park. The drive will give you a chance to see some beautiful parts of the Driftless Region and enjoy the company of whoever you’re traveling with. You’ll see beautiful timber covered hills, lush green valleys, numerous trout streams, limestone cliffs, and scenic farmland.

Once you arrive at Hillsboro, you’ll want it to be 11am, as this is when the first stop on the tour opens, so be sure to plan out your breakfast and travel time correctly. The Hillsboro Brewing Company will be your first stop along the tour and is a great place to start your brewery and winery adventure. They offer a variety of ales, lagers, IPAs, porters, sours, seltzers, and more all brewed locally by the 2e Brewery. The historic, newly restored turn-of-the-century building and the gift shop are also a big draw for this brewery. While there, you might want to try one of their delicious appetizers.

man drinking

Photo by Joey Nicotra


After a beer or two, or a flight of beer at Hillsboro Brewing Company, you can head out on the road again to your next tour destination. From Hillsboro, head southwest on Highway 82 and continue on this through La Farge, until you arrive at the next destination, Viroqua, WI. Here you’ll find the next stop on your winery and brewery tour, Tangled Hickory Wine Bar and Cocktail Lounge.

This unique bar located in the heart of downtown Viroqua opens at 2pm on Saturdays and has a wine shop within, featuring the best wines of the Driftless Region and beyond! If you’re ready for lunch, the bar offers bistro-style dishes, seasonal delicacies, decadent desserts, as well as craft beers, martinis and cocktails. Best of all, if you’d like to take a short break from driving, there is a game room in the back with pool tables, darts, foosball, pull tabs, cards, and video poker.

After lunch and drinks at Tangled Hickory, Viroqua is a great place to shop small, local businesses, for books, records, cheese or antiques & vintage. Now, you are ready to head to your next tour destination, Vernon Vineyards. Located just outside of Viroqua, Vernon Vineyards serves 100% local wine all grown on the hills of the Driftless Region. On Saturdays and Sundays, the vineyard is open between 12pm and 5pm, making it the perfect place to enjoy outdoor seating on a sunny day, complete with scenic views of the land and vineyard. Visitors can enjoy a guided wine tasting, and let the friendly, knowledgeable staff find an enjoyable Wisconsin made wine for everyone.

pouring Wine

Photo by Photo Nic


As evening approaches you should have enough time to hit the last two stops on the winery and brewery tour, if you time your day out right and don’t spend too much time at one place. From Vernon Vineyards, head back towards Viroqua on Highway 14 and then head south to the next destination, Ferryville and the next stop, Sugar Creek Winery of Wisconsin. Sugar Creek has a variety of wines to sample and buy to take home with you.

You’ll make the final stop of the tour by heading back to Westby to Branches Winery. Head north on the Wisconsin Great River Road for a scenic view of the sunset over the Mississippi River, especially during the summer, until you reach Genoa. If you have any fishermen with you who want to try their hand at fishing in Driftless Wisconsin plan to bring along your poles and stop at Captain Hook’s/Clements Fishing Barge in Genoa. Then head back up to Viroqua and finally arrive back in Westby for the last stop of the day. You’ll be able to make it to your final destination with plenty of time to spare for relaxing and wine tasting. Especially since the winery is open from 1pm to 8pm on Saturdays, and 1pm to 6pm on Sundays.

Branches Winery’s wines range from dry reds and crisp whites to sweet table and dessert wines, so you’re sure to find something you’ll like. If you’re ready to eat an early dinner, or grab some appetizers to hold you over, Branches has outdoor wood-fired pizzas, local cheese and charcuterie plates, and desserts. Make sure to explore the beautiful tasting room, as well as the surrounding area and outdoor patio for the full experience.


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Driftless WisconsinThere is simply no better place to explore, by car, by bike, or by boat. The scenery when you explore the Driftless Wisconsin Area is unmatched. The history is fascinating. The people and communities are diverse. Around every bend of the road, every twist of the river, something interesting awaits.

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