The Strangest Road Names in Illinois and How They Got Them
Just a short drive south of Chicago, the village of Oak Brook offers a surprising lesson in local lore along its quirky 22nd Street. Often mistaken for a typical suburban artery, this stretch gained fame for its unofficial nicknames, including “The Road to Nowhere.” The name stems from Oak Brook’s unique urban planning in the 1950s and ’60s, where the road once abruptly ended at agricultural fields before the boom of shopping centers and office parks. Visitors can explore the Oakbrook Center mall nearby, a sprawling retail and dining complex, to contrast the area’s rapid suburban development with the road’s humble beginnings. This juxtaposition between past and present makes 22nd Street a curious emblem of Illinois’s suburban evolution, best experienced on a crisp fall afternoon when the leaves add rich hues to the otherwise modern landscape.
Moving to the heart of Springfield, about three hours southwest of Chicago, you’ll find the historic district around Walnut Street, notably home to the Dana-Thomas House. This street’s name might not seem strange until you delve into the story behind the neighborhood’s naming conventions. Walnut Street, along with many others in Springfield, reflects a time when local streets were named after native trees, yet the Dana-Thomas House itself, designed by Frank Lloyd Wright, stands out with its organic architecture and intricate stained glass. Walking the Walnut Street corridor during spring, visitors can appreciate not just the verdant tree inspiration but also the architectural harmony Wright created, blending nature with design. Here, street names become a living homage to Illinois’s natural heritage, intertwined with artistic innovation.
Further east, in the town of Galena near the Wisconsin border—about a three-hour drive northwest of Chicago—one encounters the intriguingly named Main Street, but with a twist. Galena’s Main Street is renowned for its steep incline, earning it the nickname “The Hill.” This crooked, hilly stretch is unlike the flat plains typical of much of Illinois. Visitors strolling along Main Street will find well-preserved 19th-century buildings housing art galleries, boutiques, and eateries. The street’s topography is a vestige of Galena’s mining past, as the town sits atop lead deposits that once fueled a bustling industry. Visiting in summer or early fall offers the best views of the Mississippi River valley from the Hill’s summit, making the steep climb a rewarding journey through history and geography combined.
Traveling south to Carbondale, roughly a five-hour drive from Chicago in southern Illinois, you’ll encounter the curious name of Giant City Road, leading into Giant City State Park. This road’s name offers a clue to the park’s dramatic natural features—massive sandstone bluffs that rise above the Shawnee National Forest. The park’s Giant City Nature Trail, a moderate 2.5-mile loop, takes hikers past these imposing rock formations and through dense woodlands. The unusual name evokes the towering scale of the park’s rock “giants,” a stark contrast to the flat farmland common in much of Illinois. Early autumn is the prime season to visit, as the vivid fall colors frame the sandstone cliffs, creating a landscape that feels otherworldly and perfectly suited to the road’s grandiose title.
Out in the western part of the state, near the Mississippi River town of Nauvoo, about 130 miles west of Chicago, you’ll find Mormon Trail Road. This name is steeped in the history of the Latter-day Saint movement and their brief but impactful settlement here in the 1840s. The road traces part of the path used by early Mormon pioneers as they established the city of Nauvoo before migrating westward. Visitors to Nauvoo can explore the Nauvoo Historic District, where restored homes, a temple replica, and interpretive centers tell the story of this religious community’s rise and forced exodus. Walking or driving along Mormon Trail Road during the mild months of late spring or early fall provides a reflective experience, connecting a seemingly ordinary route to a profound chapter in Illinois and American history.
In the Chicago neighborhood of Wicker Park, about three miles northwest of downtown, you’ll find the delightfully named Avenue of the Saints, a highway that connects St. Paul, Minnesota, and St. Louis, Missouri, but cuts through Illinois with a curious presence. Though not a street in the traditional urban sense, this highway’s name pays homage to its religious roots, referencing the patron saints of these two major cities. Exploring nearby Wicker Park itself offers a different kind of pilgrimage—a cultural and artistic journey through vibrant street art, indie music venues, and eclectic cafes. The Avenue of the Saints runs just beyond this hub of creativity, a reminder of the layered identities that Illinois roads can embody, blending spiritual significance with urban cool. Late spring evenings, when the neighborhood buzzes with life, highlight this contrast perfectly.
Finally, in the small town of Metropolis, situated on the Ohio River about 330 miles southeast of Chicago, you’ll encounter Superhero Boulevard. This name reflects the town’s playful embrace of its Superman-themed identity, boasting a giant Superman statue and a dedicated museum. The boulevard leads visitors past comic book murals and to the annual Superman Celebration, which honors the legendary comic strip character who supposedly hails from this Illinois town. Walking down Superhero Boulevard, especially during the summer festival, feels like stepping into a comic book world brought to life—a strange and wonderful detour from the more conventional small-town roads elsewhere in the state. The vibrant colors and spirited decorations make Metropolis a memorable stop, where road names are not just labels but invitations to adventure.
Each of these roads in Illinois carries more than just cars—they carry stories, histories, and sometimes outright oddities. From suburban sprawl to sandstone giants, from religious migrations to comic book legends, the state’s strangest road names invite travelers to look beyond the asphalt and discover the surprising tales that shape Illinois’s landscapes and communities.