Start at a downtown Chicago sensation: Ghirardelli Ice Cream & Chocolate Shop, which opened a new location on Michigan Avenue in the historic Wrigley Building, not far from the kick-off of Route 66 in Illinois. We recommend going straight to the big and bustling ice cream bar, where you can order single scoops, generous sundaes or an Earthquake topped with nuts, fruits and syrup piled on eight scoops of ice cream (it feeds four!). Your sweet creation is best enjoyed upstairs, where you can overlook the Chicago River.
Once you set off on the Mother Road and the city unfolds into countryside southwest of Chicago, you’ll encounter Braidwood and some familiar faces. Statues of Elvis Presley, Marilyn Monroe and James Dean welcome you to Polk-A-Dot Drive In, a roadside stop since 1956. It’s pure retro, from the black-and-white checkered floor to the records spinning in a vintage jukebox. While the antique gas pump/gumball machine will beckon, save your sweet tooth for the main event: a large sundae made with creamy vanilla ice cream, chocolate sauce and a perfect cherry on top.
As you ramble down the Mother Road in central Illinois, join the locals at their favorite community gathering spot, Palms Grill Cafe in Atlanta. Opened in 1934, closed in the ’60s and reopened in 2009, it stays true to its history—right down to bingo nights and blue plate specials. Stake your claim to a vinyl chair at the counter and get what you came for: good old-fashioned home cooking. The pies are award winning and rivaled only by sundaes made from hand-dipped ice cream. Choose from chocolate, strawberry and caramel.
It would be tempting to fill up on the seared-edge burgers at Krekel’s Custard & Hamburgers, a family-owned stand off Route 66 in Springfield. But that wouldn’t be fair to its dessert menu, which has incredible sundaes with a choice of eight toppings. Get a cool vanilla swirl topped with pineapple, raspberry, fudge and other delights. Grab your order at the counter and dig into it outside at a picnic table under the glow of the Krekel’s neon sign.
Shoot back even further in time at Doc’s Soda Fountain in Girard, which opened in 1884 as a drug store. In 1929 this cheerful pit stop, found between Springfield and St. Louis, tacked on a soda fountain. Today, three generations of owners later, they still pour drinks the retro way: by putting syrup in a glass, adding soda water and pressure-squirting more soda into it. For a bigger indulgence, order an ice cream sundae, a dreamy concoction of hand-dipped ice cream and drizzled-just-so toppings. Adjoining is the free Deck’s Drug Store Museum, filled with apothecary bottles and memorabilia.