Samantha begins her trip in an unlikely but fascinating place--Old Joliet Prison--where she meets with former warden, Dennis Wolff, to find out what life was like at the prison and how the classic film The Blues Brothers came to be within its walls. In true John Belushi/Dan Akroyd style, Samantha meets up with a fellow traveler outside the prison gates--best friend Christina Burns--and they head to the iconic Polk-a-dot Drive-in for some classic American fare. Over burgers and fries, Route 66 historian and author, John Weiss, gives our travelers his insider knowledge of the best places to stop along the way. Samantha and Christina make a pit stop at the Pontiac Oakland Auto Museum for a close-up view of some of the flashiest cars ever to travel the mother road. Every fascinating place along the way deserves a quick stop--including Funks Grove Maple Sirup, where Samantha tries the bourbon-flavored sirup and learns why there's no "y" in this sticky place's name. In McClean, Samantha and Christina find America's Playable Arcade Museum chock-a-block full of hundreds of classic and fully functioning games and pinball machines. In Springfield, Samantha becomes immersed in the world of our nation's 16th president at the Abraham Lincoln Presidential Library and Museum. Next stop is the Route History Museum where Dr. Stacy Grundy illuminates what Route 66 was like for Black travelers in the era of Jim Crow and sundown towns. Before leaving the Illinois capital, Samantha enjoys a culinary original at the Cozy Dog Diner. She and Christina lunch with Buz Waldmire--brother to famous Route 66 artist Bob Waldmire (whose "road yacht" Samantha and Christina encounter along the way. At the Ace Neon Sign Museum, Dennis Bringuet recalls memories of the Cozy Dog Diner while he shows Samantha and Christina one of the world's best collections of vintage neon signs. Samantha follows the red brick road portion of Route 66 in Auburn to the Cahokia Mounds, a UNESCO World Heritage Site, and home to remains of the most sophisticated prehistoric native civilization north of Mexico. Sam and Christina end their journey with a selfie in front of the old Chain of Rocks Bridge and the mighty Mississippi River just beyond.