Route 66: Illinois & Missouri Edition

12 STOPS | 420 MILES | 7 hr 37 min

In 1946, when Bobby and Cynthia Troup drove their Buick convertible from the East to the West coast in hopes of finding a future writing songs, Cynthia suggested to Bobby that he write one about Route 40. But Bobby found Route 40 boring. When they got to Illinois and hit Route 66, something clicked. Bobby was inspired. He wrote (Get Your Kicks on) Route 66, which has become America’s anthem of  highway travel, covered by hundreds of artists from Nat King Cole (who was first to record it) to Asleep at the Wheel. There is no record of what Bobby and Cynthia ate as they traveled the highway that “winds from Chicago to L.A., more than 2000 miles all the way,” but we can assure you that as you head southwest out of Chicago, there’s a bounty colorful restaurants on or near the old Mother Road. This leg of the journey begins just outside Chicago and goes down through St. Louis and into Missouri.



Saturday-night splurge meals are Merichka's specialty, but the Roadfood lure is Poor Boy Steak -- an under-$10 sandwich sopped with margarine & garlic.


Green Gables

Green Gables is a middle-of-nowhere tavern / grocery store / restaurant serving central Illinois' scrumptious smashed crispyburgers.


Shannon’s Five Star

A large, friendly diner / coffee shop along old Route 66 in Illinois, Shannon's is a place for hearty breakfast, lunch, and dinner with truck-stop ambience.


Sunrise Cafe

In this Springfield diner, burgers are crisp-edge yummy. Breakfast is served all day. Sunrise dinner specials are fried chicken Tuesday and walleye Friday.


Joe Rogers Original Recipe Chili Parlor

The hot-oil chili that is a specialty of Springfield, Illinois, comes in six degrees of heat at Joe Rogers, from MILD to FIREBRAND. The latter is ferocious.

Must Eats

Charlie Parker’s

Charlie Parker's is an out-of-the-way Quonset hut diner specializing in huge pancakes and the Springfield, Illinois, signature dish, the horseshoe.


Cozy Dog

Dipped in batter and deep-fried when ordered, the Cozy Dog has vivid crunch and succulence. It's an Illinois Route 66 landmark.

Must Eats
Natalie’s Cakes & More

Natalie’s Cakes & More

The specialty is caramel cake, moist and buttery, at Natalie's, a charming neighborhood bakery that survived the Ferguson, Missouri, riots, and now thrives.


C&K Barbecue

A humble, take-out-only BBQ, C&K smoke-cooks the best versions of St. Louis ribs, pork steaks, chicken, and hot links, plus pig ears and snoots.


Ted Drewes

Ted Drewes’ frozen custard, a Roadfood legend of St. Louis, Missouri, is fresh, pure and tons of fun. Must-eat: a concrete milk shake, thicker than thick.


Connelly’s Goody Goody Diner

In this 1931-vintage St. Louis, Missouri diner expect to enjoy good hamburgers, chili mac, and that all-in-one breakfast dish known as a slinger.

Must Eats

A Slice of Pie

Central Missouri's premier pie shop, A Slice of Pie is just off I-44 in Rolla. pies, cakes, and cheesecakes all are outstanding.

Must Eats