Girlfriend Getaway: Wisconsin Wineries and Rustic Roads

Planning a weekend retreat with the girls? Dare to be wild and explore Wisconsin's rustic roads. Started more than 40 years ago, the Deptartment of Transportation’s Rustic Road Program features 122 of the state’s prettiest stretches of roads and places, most off the beaten path. View the DOT's interactive Rustic Roads Guide.

Take a peek at these five getaway ideas that feature wine tasting and lodging along with gorgeous drives. Then get your play clothes on. It’s road trip time!

Northeast Wisconsin

Door County

See: Just outside Baileys HarborRustic Roads 38 & 39 offer a drive through a fragrant boreal forest and a view of the Cana Island Lighthouse and Lake Michigan Shoreline.  Stop at the Toft Point State Natural Area, a national natural landmark with amazing mosses, flora and plants, and the adjacent Ridges Sanctuary with its five miles of hiking trails. 

Sip: The award-winning Stone’s Throw Winery in Egg Harbor remains true to the craft of artisan wine-making. Choose from several wine tasting tours, and be sure to try their oak barrel-fired pizza or Italian tapas. Play bocce, too!   

Stay: Luxury is yours at the Blacksmith Inn on the Shore. Because you’re worth it!  Each of the 15 guest rooms offers a fireplace, in-room whirlpool, lake view and private balcony. The best part is that you’ll be rested for a day of girlfriend fun in Door County, like zip-lining at Lakeshore Adventures!

Southeast Wisconsin

Lake Geneva

See: Just minutes outside of the bustling downtown, the tree-lined Rustic Road 29 is 2.7 miles of beautiful countryside with grand estates and rolling hills. Afterwards head back to town for Lake Geneva’s fabulous shopping and boutique district. 

Sip: Studio Winery is a hip place to sip! Cool art pieces and vintage recording equipment give the place its urban studio vibe. Sample wines with names like Amadeus, Joplin and Hendrix. Live weekend music is sure to get you and your girlfriends out on the dance floor.   

Stay: Overlooking peaceful Lake Como, The Ridge Hotel is a great place for girlfriends to unwind and rejuvenate. Aside from luxurious rooms and suites, there’s a spa for pampering and three on-site restaurants to choose from: the bean + vine coffee bar, the elegant and eclectic Crafted Americana, and trendy Bar 55 on the Veranda with its state-of-the-art 12-foot fire pit and live weekend entertainment.  

South Central Wisconsin


See: Wildlife abounds on the nearly 6-mile Rustic Road 110, which meanders through farmland, small lakes, marshland and rolling hills. It’s also close to the Lower Wisconsin Riverway scenic byway and the Lodi Marsh State Natural Area.

Sip: Established before the civil war, Wollersheim Winery & Distillery is a National Historic Site with a striking limestone building. Look in the underground aging cave and tour “Bob’s Garden,” which includes plants with aromas and flavors found in wine varietals.

Stay: The Inn at Wawanissee Point sits atop the Baraboo Bluffs and offers a mesmerizing, 36-mile panorama of the Lake Wisconsin valley and beyond. Stay at this peaceful adults-only retreat to spend quality time with your favorite people.

Southwest Wisconsin


See: The only rustic road section that follows the Mississippi River, Rustic Road 99 is close to Wisconsin’s Great River Road and the charming town of Potosi with its popular Potosi Brewery and National Brewery Museum.

Sip: Talk about catering to women! Whispering Bluffs Winery offers handmade chocolates that you can pair with your wine. Wine names pay tribute to birds, like Rose-Breasted Grosbeak (Pinot Noir), Kingfisher (Merlot/Malbec) and Indigo Bunting (Blueberry).

Stay: Lots of gabbin’ can take place at the spacious cabins of Pine Point Lodge. Three cabins are for six people and one is for 12. Kitchens are fully equipped. Towels and bedding are provided, but bring your own pillows.

Northwest Wisconsin

Maiden Rock

See: It’s gravel but it’s awesome! Just over four miles long, Rustic Road 51 crosses a trout stream, frequently in the midst of woodlands. A few miles away is a wayside marker and a replica of the cabin that inspired Laura Ingalls Wilder to write "Little House in the Big Woods."  

Sip: All things are apple at Maiden Rock Winery & Cidery! Enjoy snappy and distinctive hard cider flavors, crafted in the farmhouse tradition of southwestern England. Tours are customized to the group and may include a short orchard walk. 

Stay: A former schoolhouse that was built in 1906, Maiden Rock Inn says “sleeping in school is cool.” Four unique guest rooms boast personalities of their own, ranging from a hand-painted claw foot tub to Jacuzzis. Begin your day with a delicious sustainable breakfast, made from scratch.   

Check out even more scenic drives along rustic roads!