Wisconsin Bike Trails: Five Funky Towns to Bike To

Wisconsin towns put the fun in funky. Here is a list of a five towns—each with its own personal twist. There are many bike trails and winding back country roads leading to these funky destinations, so why not ride to town?

Mount Horeb

Mount Horeb’s Scandinavian charm puts this destination at the top of our funky list. The town has numerous carved wooden troll sculptures guarding the Trollway. Ride on down and stop for a great photo op with one of these funky sculptures.

While you’re here, make a pit stop at the Grumpy Troll Brewery for a beer and some lunch or check out the numerous antique shops and galleries in the downtown area. Expert bicyclists mustn’t miss out on riding the Driftless region. Offering more than 10,000 feet of elevation, it’s sure to be a good challenge!


Viroqua describes their town as “rich history mixed with a funky cultural renaissance.” Being at the “doorway to the Driftless Area,” and at the edge of the Ocooch Mountains, the area provides many biking opportunities.

While biking through, stop at the Viroqua Public Market for food, crafts and antiques. If you brought kids don’t let them miss out on climbing the wooden dragon in Eckhart Park!


The town of Plymouth features 24 hand painted murals of the historical significance of the town’s business history, which gives this town a little funk. Biking here is made easy due to it being one of the trailheads for the Old Plank Road Trail which is a 17 mile long trail stretching from the city of Sheboygan to the village of Greenbush.

While you’re here, stop for a micro-brew and pizza at DeO’Malley’s Pizza Pub, located in a building that is more than 100 years old.

Prairie du Sac

Prairie du Sac, combined with nearby Sauk City, makes the funky list due to the conjoining of these two Riverway Towns.

While in Prairie du Sac, indulge yourself in all things riverside beginning with a winery tour and tasting at Wollersheim Winery, set in the bluffs on the Wisconsin River. For lunch head to the Blue Spoon Café, which provides riverside seating and serving a Euro-style cuisine.

New Glarus

Don’t miss the Swiss-ness of the town known as New Glarus. This town is locally renowned for the infamous Spotted Cow, a farmhouse ale, from the New Glarus Brewing Company. A great place to satisfy your appetite is Glarner Stube restaurant serving fine Swiss and American cuisine, with old world charm. A little ways south of town is the New Glarus Woods State Park which attaches to the 22-mile Sugar River State Trail that extends from Brodhead to New Glarus.

If you are biking from Madison or Monroe, the Badger State Trail can get you there. They say you know you’ve reached New Glarus when you can hear the cow bells!

This entry was posted in Multi-use Bike Trails