Road Trips
Eat Across Route 66

Like the Mother Road itself, Calumet Fisheries is a vintage American classic. Opened in 1948, the South Side shack is one of the last seafood smokehouses in Chicago. There’s no indoor seating, so grab one of the two outdoor tables overlooking the Calumet River or simply enjoy containers of smoked and fried fare in your car. Smoked on-site for hours over oak logs, Calumet’s exquisitely seasoned salmon, trout, sturgeon, and giant shrimp are just as delicious over a dashboard.

You’ll see the giant, smiling sausages long before you reach the Cozy Dog. The joint claims to be the birthplace of the corn dog—just don’t call it that in Springfield. Here, founder Buzz Waldmire created a battered-and-fried hot dog on a stick known as the “cozy dog” in the 1940s. The alleged birthplace of the fairground favorite is chockablock with hot-dog history and paraphernalia, from posters of proud mothers bottle-feeding baby hot dogs ketchup to a collection of historic cozy-dog cooking tools.

The Luna Café is the kind of local watering hole where out-of-towners might feel like they hear a record-scratch when they enter; the kind of spot where you order a beer and whatever grub they have, and you don’t fuss over it too much. Here, it’s the space, not the menu, that’s the star. Built in 1924, Luna is older than Route 66 itself. During the heyday of Chicago gangsters, Al Capone favored the café as a good spot to meet up with mobsters in the Granite City area. The gangsters are gone, but one relic of Luna’s seedy past remains: its vintage neon sign. According to local lore, the red cherry in its glowing cocktail once acted as a code. When the cherry lit up, it meant it was time for “adult entertainment.”

From its humble exterior, Leong’s Asian Diner almost looks more like a barn than a Chinese restaurant. But to pass by this gem would be passing by the home of a local classic. Created by David Leong in the 1960s, Springfield-style cashew chicken offered a riff on Cantonese fare that appealed to fried-food-loving locals: battered-and-fried chicken nuggets coated in cashews, green onions, and a gravy-like sauce. Although Leong passed away in 2020, his son still makes the specialty at the diner today.

In the early 1900s, an influx of Lebanese immigrants arrived to work in the oil fields around what is now Tulsa, Oklahoma. To feed this growing community, a collection of Lebanese supper clubs popped up. Today, Jamil’s is the last remnant of this delicious diaspora. You can still taste Jamil “Jim” Elias’s signature blend of Lebanese flavors and sweet, smoky Oklahoma steakhouse fare. Don’t miss out on the beef kabobs slathered in za'atar-spiced barbecue sauce.

Just pull over at the glowing, 66-foot soda bottle. Even though Pops opened in 2007, everything about it screams retro Americana. Designed in the model of a vintage gas station, it’s also a restaurant and soda shop. Whether you’re looking for classics or for quirky flavors (beef jerky, anyone?), Pops has 700 different sodas to choose from. Even the food menu includes soda-inflected fare, such as the delicious root beer bread pudding, which uses Pops’ house-made root beer.

In the 1920s, drivers on Route 66 knew to pull over in the small town of El Reno, Oklahoma. There, in a small, eight-stool greasy spoon, the cook slung the sweet-and-savory specialty known as fried onion burgers. An ingenious Depression-era hack to stretch paltry meat supplies, the burgers were made by smashing shredded onions into one side of a lean patty, sizzling them into the meat as it cooked. The crispy, caramelized onions perfectly complemented the ground beef and an Oklahoma favorite was born. Although the original Hamburger Inn closed (there’s a new one a two-hour drive south, in Ardmore), you can still get a fried onion burger in El Reno at Sid’s Diner.

After it was built in 1936, the U-Drop Inn’s Art Deco building and its tulip-topped tower were one of the most eye-catching stops along Route 66. Though its days as a gas station and restaurant are behind it, the U-Drop’s visitor center is still a beautiful place to stop, refuel with coffee, soda, or ice-cream floats, and learn about this Route 66 relic. Electric car users take note: Even though it no longer pumps gas, the U-Drop installed a Tesla Supercharger station in 2014.

While other items on this list might claim to be classic Americana, this is the only spot making this land’s original food. At the Indian Pueblo Kitchen, chefs serve dishes that celebrate the culinary heritage of New Mexico’s Pueblo people prior to Christiopher Columbus’s arrival to the Americas in 1492. The “Pre-Contact” portion of the menu is a sumptuous feast of indigenous ingredients, including pan-seared trout with yam puree, prickly pear syrup, and fried sweet-potato strings; sumac-seared bison with pickled squash and pumpkin oil; and slow-stewed berries baked under a maple pepita-and-pecan-crumble crust.

A largely empty stretch of desert road in Arizona is one of the last places you might expect to find world-class sake. But that’s exactly where Atsuo Sakurai has set up his tiny, award-winning sake brewery. Visitors can get a tour, a tasting, and a few bottles to take home, but if you happen to swing into town when the brewery’s closed, fear not. Local liquor stores and even gas stations also carry the Japanese liquor.

Open since 1912, Sultana Bar is packed with history, from its ceiling to its underground tunnels. The latter were originally used for drug-running, but later for sneaking in booze during Prohibition. While visitors can’t access these subterranean passageways, they can still enjoy cold beers amidst retro neon signs and taxidermy, including a large stuffed cougar looming over the bar.

While many Route 66 attractions tower above the ground, this restaurant hides 200 feet beneath it. Take the elevator down 21 stories to reach the Caverns Grotto, a small spot specializing in American comfort food that’s tucked inside the sprawling, 345-million-year-old cave network known as the Grand Canyon Caverns. Meals aren’t cheap—there’s a flat fee of $49.95 for lunch and $69.95 for dinner—but each includes a cavern tour, which normally costs $22. The space has only four tables, so reservations are recommended (928-422-3223).

A blend of dino-themed roadside kitsch and 1950s pop culture paraphernalia, Peggy Sue’s 50's Diner and Diner-Saur Park is the perfect place to end your edible journey across Route 66. After eating burgers and shakes at the vintage-style ice-cream counter, head out back to explore the garden’s 10-foot-tall metal dinosaurs (plus one King Kong), all amidst the beautiful backdrop of the Mojave desert.