The Strangest Road Names in Wisconsin and How They Got Them
About 40 miles northwest of Milwaukee, the quaint village of Cedarburg offers a glimpse into Wisconsin’s quirky past with its famously named “Kissing Bridge Road.” This stretch winds through the historic Cedarburg Covered Bridge, one of the oldest of its kind still in use in the state. The bridge’s romantic name doesn’t come from chance; local lore says young couples would sneak kisses while crossing, safe from the eyes of chaperones. Walking the bridge during the golden light of late afternoon in autumn, when the surrounding oaks blaze in fiery hues, makes the story come alive. Visitors can explore Cedarburg’s charming downtown, full of artisan shops and galleries housed in preserved 19th-century buildings, the perfect complement to this nostalgic route.
Further north, about 30 miles northeast of Eau Claire, the small town of Chippewa Falls hosts a road that always sparks curiosity: “Pigeon Street.” This street’s name might seem ordinary, but it harks back to the area’s early days as a hub for pigeon hunting and pigeon racing, popular sports in the 19th century. While walking the scenic Duncan Creek Trail nearby, a 5-mile out-and-back trail known for its gentle terrain and riverside views, visitors get a sense of the natural habitat that once supported large pigeon flocks. The trail’s peacefulness contrasts with the bustling town center, where the Jacob Leinenkugel Brewing Company invites visitors to taste local craft beer with deep roots in the region’s German immigrant heritage.
In the southwestern corner of Wisconsin, near Mineral Point, lies “Dirty Hollow Road,” a name that piques the imagination. Mineral Point itself is a gem, about a 50-minute drive southwest of Madison, known for its rich lead mining history and vibrant artist colony. The road’s name dates back to the 1800s when the hollow was a muddy, often impassable spot frequented by miners and workers. Today, visitors can hike the nearby Governor Dodge State Park, roughly 10 miles east of Mineral Point. The park’s rugged terrain features over 40 miles of trails, including the scenic Cox Hollow Trail which offers glimpses of limestone bluffs and serene lakes. Springtime, when wildflowers bloom and the park’s many bird species return, is an especially enchanting time to experience the area’s natural beauty and industrial past.
In the heart of Madison, the state capital, one of the most unusual names is “Shady Hollow Court,” nestled in a leafy neighborhood near the University of Wisconsin campus. This street’s moniker reflects its origins as a shaded enclave for university professors and artists seeking quiet inspiration away from the city bustle. Nearby, the Olbrich Botanical Gardens offer a peaceful retreat with their stunning Thai Pavilion and vibrant outdoor plantings, ideal for a reflective afternoon stroll. Early summer, when the gardens are in full bloom and the evenings linger long, is when this part of Madison truly shines, blending urban culture with natural elegance.
Traveling about 60 miles north of Green Bay, the town of Pulaski is home to “Badger Road,” named with a hint of regional pride and local history. The “Badger” nickname comes from Wisconsin’s mining past; early lead miners were called “badgers” because they often lived in tunnels dug into hillsides. Pulaski, known as the “Polish Capital of Wisconsin,” hosts an annual Pulaski Polka Days festival that celebrates its immigrant heritage with lively music and dance. Alongside the festivities, visitors can explore the Pulaski Community Park, perfect for picnicking and catching a view of the gently rolling hills characteristic of northeastern Wisconsin. Fall is a particularly festive time, with colorful foliage and harvest celebrations adding to the charm.
In the northern reaches of the state, near the Apostle Islands National Lakeshore off Bayfield, there’s a place called “Nonesuch Bay Road.” This name harks back to the “Nonesuch Mine,” a short-lived copper mine that was notoriously difficult to exploit despite promising deposits. Bayfield is about a two-hour drive north of Duluth, Minnesota, and serves as the gateway to the islands. Visitors can embark on boat tours from Bayfield’s waterfront to explore sea caves and pristine beaches. In summer or early fall, the mild weather and clear waters make for unforgettable kayaking and hiking experiences on the islands, where the region’s industrial history meets stunning natural beauty.
Closer to the Mississippi River, in the charming river town of Prairie du Chien, about 80 miles west of Madison, “Funky Star Road” stands out as a name that invites questions. This road’s name is rooted in local legends about a colorful 1970s nightclub once located nearby, known for its eclectic music and late-night dances. Visitors can explore the Villa Louis Historic Site in town, a beautifully restored 19th-century mansion that tells the story of the area’s French-Canadian and American frontier heritage. Summer brings lively reenactments and garden tours, adding layers of cultural depth to a place where history and modern quirks coexist.
Each of these roads tells a slice of Wisconsin’s varied story, from mining towns to university neighborhoods, from immigrant festivals to lakeshore adventures. Traveling through the state offers more than just scenic drives; it’s a journey through names that capture the character, humor, and heritage that make Wisconsin uniquely inviting. Whether crossing a covered bridge at sunset or paddling among the Apostle Islands, these places offer tangible connections to the stories behind the strangest road names you’ll find anywhere in the Midwest.