Enjoy a local brew or glass of wine when craving the solace of the outdoors, with enough room to breathe and keep a social distance. Driftless Wisconsin can offer you the outdoor fun you love, the local experiences you want, with the space you need.
Look forward to your future vacation in Southwest Wisconsin and learn what the Driftless is all about. Click to order a map and start the daydream.
Click to order or download a map and start the daydream.
Featured Photo by Drew Beamer
Hillsboro Roadhouse
The best way to drink like a local in Driftless Wisconsin is to pull up a stool at one of the area’s hometown bars and get a taste of both the drinks and the people. A great place to start is Hillsboro Roadhouse in Hillsboro.
With its laid-back, small-town atmosphere and a solid food and drink menu, the Roadhouse is one spot in the Driftless Region that truly makes everyone feel welcome. Pair your favorite drink with an appetizer, a full dinner, or stop in for a cold beverage and a fun setting to catch your favorite game.
Hillsboro roadhouse
Photo by rikkia hughes
Tangled Hickory Wine Bar
If you would rather sip on a glass of wine than a cold beer, then Tangled Hickory Wine Bar in Viroqua is the perfect bar for you to visit in the Driftless Region. Complete with cozy seating and an inviting atmosphere, Tangled Hickory Wine Bar is great for relaxing with friends over a drink. They offer an extensive wine menu with many wines that originate from the Driftless Region, as well as locally sourced bistro-style food. If you’re not a wine drinker, you can also order craft beers, martinis, and cocktails. The wine bar also features a game room with pool tables, darts, foosball, cards, pull tabs, and video poker for guests to enjoy while sipping on their favorite beverage.
Photo by Moritz Mentges
Kickapoo Creekside
Just a short distance from the Kickapoo River, Kickapoo Creekside is the perfect bar to grab a beverage and enjoy the beauty of the Driftless Region. Located in Readstown in the heart of the Kickapoo Valley, Kickapoo Creekside offers small-town comfort and charm, as well as friendly faces behind the bar. You can plan on stopping at Kickapoo Creekside for just a few drinks, including some delicious specialty cocktails, but their food is popular with locals and visitors alike, especially their steak and seafood dinner options. This bar and restaurant offers a comfortable atmosphere to watch the game or visit with friends and family and enjoy great food, drinks, and service.
Photo by Meritt Thomas
Hillsboro Brewing Company
Hillsboro Brewing Company in Hillsboro is another great choice for grabbing a drink in the Driftless Region. You can stop in for drinks, food, or both any day of the week, but the brewery is known for their great drink selection including 26 different locally brewed beers. Beer drinkers can choose from a selection of ales, hefeweizens, lagers, IPAs, stouts and porters. Hillsboro Brewing Company also has you covered with their locally made seltzers and a variety of mixed drinks, if you’re not much of a beer drinker. The drinks pair great with their appetizer and food options, making the brewery a great place to hangout with friends and family and enjoy some drinks brewed right in the Driftless Region.
There 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.