Text by Tammie

  Henry’s Drive-In on Ogden Avenue (Old Route 66) near Austin Boulevard in Cicero, Illinois, bills itself as serving food in a way that “It’s a Meal in Itself!” Henry’s is named after William Henry.   Henry’s Drive-In is famous for:   n     Chicago-style hot dogs n   An outdoor neon sign of a giant hot dog topped with fries n   Being a classic since 1950.   More here :  

  A Chicago, Illinois, man who won the 2024 Nathan’s Famous International Hot Dog Eating Contest triumphed over seven other contestants to win the inaugural Mother Road Festival Cozy Dog Eating Championship on Saturday, Sept. 26, 2026, in Springfield, Illinois. Patrick Bertoletti ate 51 Cozy Dogs in 10 minutes to win $2,500 in the Cozy Dog Eating Championship in Springfield. Darrien Thomas of Toronto, Ontario, Canada, consumed 37 ½ Cozy Dogs for second place and a prize of $1,250. Jerome Burns of Danbury, Connecticut, ate 25 dogs for a third-place prize of $600. Semora Kludy of Charlotte, Michigan, consumed 15 ½ dogs for the $400 fourth-place price. More here .

    Bourbon, Missouri, is a town of a little over 1,500 people known as the only one in the U.S. named for bourbon whiskey.   Route 66 also went through the town in 1926.   Today, the Bourbon Economic Development Group is trying to make Bourbon “a vibrant town.”   Among stops in Bourbon worth experiencing are the 1925 Bourbon Water Tower and Country Skillet Café.   More here .    

  A specialty toy store and hobby shop as well as a BBQ lounge are on Ogden Avenue, which is Berwyn, Illinois,’ section of Historic Route 66. Berwyn’s Toys & Trains is at 7025 Ogden Ave., down the road from Cigars & Stripes BBQ Lounge at 6715 Ogden Ave. Berwyn, Illinois, is 9 to 10 miles west of downtown Chicago. Everything has a place in Route 66 history. Berwyn’s Toys & Trains keeps Route 66 alive by retaining the “original authentic style” of the building it's in that was a Chevy dealership from 1950 until 1998. Cigars & Stripes BBQ Lounge celebrates Route 66 with a rooftop “Muffler Man” giant and a sci-fi wall mural. More about all that here .  

  The Saltpeter Cave of the 1720s through 1933 in Stanton, Missouri, has turned into a tourist attraction instead of a cave for mining saltpeter to help manufacture gunpowder. Now known as Meramec Caverns, the cave system is a few miles from the old alignment of Route 66 near Stanton and Sullivan, Missouri. Meramec Caverns is open to tourists. Some of what they’ll find are:   n   “Soda straw” formations hanging from ceilings   n   Fake outlaws Jesse and Frank James   n   A failed Foucault pendulum   n   “Restored Lassie" More information is here .  

    The late American gangster Al Capone (1899-1947) has found a resting place at the Capone family gravesite in Mount Carmel Catholic Cemetery, 1400 S. Wolf Road in Hillside, Illinois.   Al Capone’s body was moved in 1952 to Mount Carmel from Mount Olivet Cemetery in Chicago, Illinois, because of vandalism.   Mount Carmel isn’t directly on Route 66, but Route 66 roadtrippers have made it a side trip due to Capone’s connection with the Mother Road. Capone and Route 66 are historically connected because he used the highway and its adjacent towns during Prohibition to move illegal alcohol and escape the law.   Capone would regularly bootleg booze between Chicago and St. Louis, according to “History.”   More here .