The First Hundred Miles of the Mother Road not only offers scenic drives and classic roadside attractions but invites you into places where Route 66’s stories are preserved, celebrated, and brought vividly to life. From world-class museums in Chicago to hidden heritage gems in small towns, every stop introduces you to the legacy of a road that’s captured the imaginations of travelers for generations.
The adventure begins in Chicago, where a rich cultural experience awaits even before your wheels leave the city streets. Close to the historic beginning of Route 66, The Art Institute of Chicago (111 S. Michigan Ave., Chicago) stands as one of the great art museums in the world. Its vast permanent collection includes iconic works such as “Nighthawks” by Edward Hopper, “American Gothic” by Grant Wood and Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.”
Not far from there, on Chicago’s bustling Museum Campus along Lake Michigan, The Field Museum of Natural History (1400 S. Lake Shore Drive, Chicago) offers something completely different yet equally compelling. Famous for housing “Sue,” the largest and most complete Tyrannosaurus rex ever discovered, this museum invites travelers to explore life on Earth from ancient deep seas to modern ecosystems. Gigantic skeletons, hands‑on displays and rotating special exhibits provide a thrilling cross between science and storytelling.
Leaving the urban sprawl behind, the route meanders south-west into Joliet, a city that encapsulates both the historic grit and vibrant spirit of Route 66 culture. The Joliet Area Historical Museum and Official Route 66 Welcome Center (204 N. Ottawa St., Joliet) offers a multifaceted introduction to the region’s past. Housed in a striking Neoclassical Revival building that once served as a church, the museum celebrates not just Route 66 but also the Lincoln Highway and local history through immersive exhibits, interactive displays and picture‑perfect photo opportunities. Here you can step into the world of “The Blues Brothers,” which filmed key scenes in Joliet and has become part of the city’s pop culture identity. Exhibits highlight the role of the Illinois & Michigan Canal in shaping early Midwestern transportation, through a collection of vintage artifacts and interpretive scenes.
Joliet also offers an array of other cultural spots that expand your understanding of the Mother Road and local history. The Illinois Rock & Roll Museum on Route 66 preserves the history of seminal Illinois musicians and bands, from Cheap Trick and Styx to Chuck Berry and Buddy Guy. This museum is a lively celebration of the state’s influence on American music, with exhibits and memorabilia that emphasize the deep connection between musical heritage and local identity – and a giftshop featuring music and Route 66 themed souvenirs.
Not far away, the Joliet Railroad Museum (90 E. Jefferson St, Joliet) lets visitors explore the engineering and stories of railroads that helped define transportation in the region, housed in a preserved early 20th‑century signal tower. And for a slice of immigrant history, the Martin & Emma Planinsek Grocery and Meat Market Museum (1314 Elizabeth St., Joliet) offers insight into the Slovenian community that helped build and shape the city.
No visit to Joliet is complete without encountering the formidable Old Joliet Prison (1125 Collins St., Joliet). This limestone penitentiary, in operation from the mid‑19th century until 2002, has become one of the most photographed structures along Route 66 and a cultural touchstone in its own right. Used as a filming location for “The Blues Brothers” and referenced in TV dramas like “Prison Break,” the prison’s history spans regional crime, Civil War era detainees, and decades of changing penal philosophies. Today, both guided and self guided tours allow visitors to explore this dramatic site.
Continuing southwest, the landscape opens into a quieter, rural rhythm in the village of Godley, where a hidden gem waits. The Illinois Route 66 Mining Museum (150 Kankakee Road, Godley) tells the story of the area’s coal mining past, including the coal rush sparked by the discovery of “black diamonds” in the 1860s and the tragic 1883 mining disaster that claimed 74 lives. Although small, this museum’s focus on community history and industrial heritage offers an intimate and poignant perspective on life along the early Mother Road.
To experience an authentic selection of vintage cars, be sure to pay a visit to Crazy ’80s Car Museum (316 W. Waupansie St., Dwight). The museum’s main show floor features a private collection of nothing but ’70s to late ’80s cars. There are no muscle cars or hot rods of the era, just the iconic mid-sized and compact cars that once populated Route 66. Decorated with Sears Roebuck & Co. mannequins, a McDonald PlayPlace carousel and other memorabilia from the era, Crazy ‘80s has something for the entire family to enjoy.
Further west, in the picturesque town of Pontiac, your journey culminates among some of the richest collections of Americana you will encounter. The Pontiac Oakland Auto Museum (201 N. Mill St., Pontiac) continues a tradition of celebrating automotive history with an extensive collection of vintage cars, memorabilia, and an impressive research library. Enthusiasts can take their time exploring the displays and even sign up for behind‑the‑scenes tours that uncover details about these classic vehicles and the stories they carry.
The nearby Museum of Gilding Arts (217 N. Mill St., Pontiac) transports visitors to another era, showcasing the craft of silver and gold leafing that was once central to architectural ornamentation and design. With artifacts and demonstrations tracing this art from ancient traditions through America’s Gilded Age, it is a unique stop that broadens understanding of how everyday objects and décor reflected larger cultural trends. The International Walldog Mural and Sign Art Museum (217 N. Mill St., Pontiac) adds color and creativity to the experience, spotlighting the work of artists whose murals now animate Pontiac’s downtown. Following your museum visit with a walk through the town to discover these murals brings Route 66’s spirit into the open air in vivid hues and textures.
At the end of the first hundred miles, the Route 66 Association of Illinois Museum (110 W. Howard St., Pontiac) invites you to step deep into the Mother Road’s soul. With vintage license plates, historical photographs, a classic VW bus featured in Disney’s “Cars” and a towering Route 66 shield mural perfect for photos, this museum is a celebration of nostalgia, community and the enduring allure of America’s most famous highway.
