Route 66 turns 100 in 2026, and there may be no better excuse to drive America's Mother Road end to end. The highway now runs 2,238 miles from Chicago to Santa Monica — shorter than its original 2,448 thanks to various realignments — and the classic diners, barbecue joints and soda fountains lining it are half the reason to make the trip. A recent roundup from Islands highlights 16 stops worth building a route around, from Illinois to California.
Start in the Loop, where the route's ceremonial start moves to Navy Pier in 2026. Lou Mitchell's, on West Jackson Boulevard since 1923, remains the classic first breakfast: fluffy omelets, doughnut holes, and coffee from the same urn since the 1950s. Nearby on Adams Street, The Berghoff traces its roots to the 1893 Chicago World's Fair — a family-run German restaurant with its own on-site brewery pouring lagers and dunkels.
Springfield, Illinois earns two stops. Cozy Dog Drive-In has fried its signature breaded hot dog in the same batter since 1946 — founder Ed Waldmire deliberately avoided cornbread batter because it was too slow — and still uses his chili recipe. A mile west, Charlie Parker's Diner sits in a 1950s-style Quonset hut (built in 1992, actually) and won a national breakfast contest with its take on the Springfield "horseshoe": open-face toast stacked with cheese sauce and fries. South in Litchfield, the Ariston Cafe has served Greek-American-Italian plates since 1924, relocating in 1929 specifically to catch Route 66 traffic.
Missouri Hick BBQ in Cuba, Missouri looks like a log cabin-barn hybrid and smokes brisket, pulled pork and sausage, with six house sauces sold by the bottle. In Arcadia, Oklahoma, Pops Soda Ranch is hard to miss thanks to its 66-foot soda bottle out front, and stocks more than 700 soda flavors alongside a full diner menu — including a bison Centennial Burger. El Reno's Sid's Diner keeps the town's "Fried Onion Capital of the World" reputation alive with onion-fried burgers, and the town's annual Burger Day once featured an 850-pound, 8-foot-wide patty.
Texas brings the theatrics. The Big Texan Steak Ranch in Amarillo, open since 1960, dares you to finish a 72-ounce steak in an hour — success means it's free. Further west, Adrian marks the exact halfway point of the route at 1,139 miles from both Chicago and Santa Monica, home of the appropriately named MidPoint Cafe and its "you're halfway there" sign.
A Route 66 centennial trip works for almost anyone: families who want kitschy photo ops, food travellers chasing regional classics, or road-trippers ticking off a bucket list before the highway's second century. The beauty is that many of these stops sit within a short drive of the historic alignment, so detours cost minutes, not hours. Just pace yourself — with this much fried food, pie and brisket on offer, the drive may take longer than planned.
