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Outside the foreboding Old Joliet Prison
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Crossing a rope bridge at Zip Chicago in Marseilles
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A hiker pauses to lookout over Heritage Corridor country
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Kayaking in Starved Rock with Kayak Morris
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NASCAR racers zipping around the Chicagoland Speedway track
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Tasting booths at Ottawa Illinois 2 Rivers Winefest
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Neck and neck drag racers on the Route 66 Raceway
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Get at the heart of Route 66: Start from the start!

The first 160-kilometer stretch of Route 66 – from Chicago through Joliet to Pontiac, Illinois – is packed with nostalgia, fun and great food. It’s the perfect start to a journey along the USA’s “Mother Road.”

Joliet: The City of Excitement

Begin your journey with a day and night in Chicago to see the sights, including the historic starting point of Route 66 at Michigan Avenue and Adams Street. Get an early-morning start for the 90-minute drive to Joliet. Enjoy breakfast at the Joliet Route 66 Diner before heading to the Joliet Area Historical Museum and Route 66 Welcome Center. Pose with statues of The Blues Brothers and learn more about the city and its attractions. Pick up a tour ticket for the Old Joliet Prison, which housed notorious real-life criminals and some fictitious ones, including Joliet Jake Blues from “The Blues Brothers” and Michael Scofield from “Prison Break.”

Shop in downtown Joliet’s unique shops, then grab lunch at Jitters or Chévere Latin Café before visiting the Old Joliet Prison. If your schedule doesn’t allow for the full tour, Old Joliet Prison Park features information exhibits about the historic site. You will be able to get some great photos for Instagram.

Order an ice cream treat at Rich & Creamy, then follow Route 66 to two neighboring racetracks just south of Joliet. Check out NASCAR racing at Chicagoland Speedway or NHRA and other drag racing at the Route 66 Raceway.

Posing with the Blues Brothers at the Joliet Historical Museum

Posing with the Blues Brothers at the Joliet Historical Museum
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Quick Detour Along the I&M Canal

Take a short jaunt west off Route 66 to several places in the I&M Heritage Corridor. Towns such as Morris, Marseilles and Ottawa that are clustered along the I&M Canal offer trendy boutiques, antique shops and a range of dining options. Pose next to Starved Rock State Park’s amazing waterfalls and rocky cliffs in Oglesby. Head to LaSalle, St. Louis, French, Ottawa and Tonti canyons for the best views in spring or winter, when the waterfalls freeze into icefalls, and check out the dramatic sandstone bluffs. After taking in the sights, head back to Route 66 and resume your drive south.

Marveling as the massive rock formations of Starved Rock State Park

Marveling as the massive rock formations of Starved Rock State Park
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