Stretching over 2,400 miles from the neon lights of Chicago to the Pacific shores of Santa Monica, Route 66 is more than just a road—it’s the “Mother Road” of the American spirit. Whether you’re a history buff, a fan of vintage kitsch, or just looking for the ultimate open-road adventure, this is your ultimate guide to a Route 66 road trip.
1. Planning Your Journey: The Basics
Before you put the key in the ignition, you need a strategy. Route 66 spans eight states and three time zones.
- How Long Does It Take? While you can “rush” it in 10 days, the sweet spot is 14 to 21 days. This allows time for quirky roadside stops and 200-mile driving days.
- Best Time to Go: * Spring (April–June): Mild weather and blooming landscapes.
- Fall (September–October): The “Goldilocks” zone—pleasant temperatures and fewer crowds.
- Avoid winter (snow in Illinois/Arizona) and peak summer (100°F+ heat in the Mojave Desert).
- Direction: The classic experience is East to West (Chicago to LA), following the path of 20th-century migrants seeking the “Promised Land” of California.
2. Iconic Stops by State
You can’t drive the Mother Road without stopping at these legendary landmarks:
Illinois & Missouri: The Gateway
- The Starting Sign (Chicago): Located at Adams St. and Michigan Ave. Grab breakfast at Lou Mitchell’s first—it’s been serving travelers since 1923.
- Gateway Arch (St. Louis): The literal “Gateway to the West.”
- Meramec Caverns (Stanton, MO): Once a hideout for outlaw Jesse James.
Oklahoma & Texas: The Heart of the Route
- The Blue Whale (Catoosa, OK): One of the most photographed pieces of roadside whimsy in the world.
- Cadillac Ranch (Amarillo, TX): Grab a can of spray paint and leave your mark on ten half-buried Cadillacs.
- The Midpoint Café (Adrian, TX): Exactly 1,139 miles from both Chicago and LA. Try their famous “Ugly Crust” pie.
New Mexico & Arizona: High Desert Magic
- Blue Swallow Motel (Tucumcari, NM): Famous for its stunning neon display and vintage “tuck-under” garages.
- Wigwam Village (Holbrook, AZ): Yes, you can actually sleep in a concrete teepee.
- Seligman, AZ: The town that inspired Pixar’s Cars. Visit Angel Delgadillo’s barber shop for a shave and a story.
3. Pro Tips for the Road
To truly “get your kicks,” follow these insider rules:
- Don’t Trust Google Maps: Standard GPS will try to push you onto the modern Interstate (I-40). Use a dedicated Route 66 navigation app or the classic EZ66 Guide For Travelers.
- Look for the Shields: Keep an eye out for “Historic Route 66” brown signs and painted shields on the pavement.
- Book Historic Motels Early: Places like the Blue Swallow or El Rancho book up months in advance for the peak season.
- The 2026 Centennial: 2026 marks the 100th anniversary of the road. Expect massive festivals and crowds throughout the year!
4. Packing Essentials
- Paper Maps: Signal can drop out in the Mojave Desert or the plains of Texas.
- A Playlist: Load up on Chuck Berry, Nat King Cole, and The Eagles.
- A Cooler: Many stretches of the road are remote; keep water and snacks on hand.
Route 66 Snapshot
| State | Highlight | Must-Eat |
| Illinois | Gemini Giant | Cozy Dog Drive-In |
| Missouri | Chain of Rocks Bridge | Ted Drewes Frozen Custard |
| Oklahoma | Route 66 Museum | Pops 66 (700+ sodas) |
| Texas | Cadillac Ranch | The Big Texan Steak Ranch |
| Arizona | Standin’ on the Corner Park | Mr D’z Route 66 Diner |
| California | Santa Monica Pier | Pier Burger |
