US 66 Road Trip: A Complete Planning Guide

Planning Your US 66 Road Trip

Before you pick a start date, it helps to decide how much of the route you actually want to drive. Some travelers do the full stretch from Chicago to Santa Monica, while others tackle a shorter section, like Oklahoma to New Mexico, over a long weekend. Either way, a bit of upfront structure saves you from scrambling for gas or a motel room at 9 p.m. in a town with none open. Our practical plan for road trip season walks through the basics of building a trip timeline that actually holds up once you’re on the road.

How Long Does It Take?

Driving the full route nonstop would take around 40 hours, but nobody actually does that. Spreading it over 10 to 14 days gives you time to stop at the roadside attractions that make Route 66 worth driving in the first place, without rushing through every town. If you’re trying to figure out how much driving is reasonable per day, the 3-3-3 rule for road trips is a useful starting point for pacing a long drive like this one.

Best Time of Year to Go

Late spring and early fall tend to be the sweet spot. Summer brings serious heat across Arizona and New Mexico, and winter can close stretches of road in the higher elevations. Shoulder-season travel also means fewer crowds at the most photographed stops.

Mapping the Classic Route

Route 66 runs through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. The road has been decommissioned since 1985, so you’ll be following a mix of old alignments, historic markers, and modern highways that trace the original path.

From Chicago to St. Louis

This stretch takes you through small Illinois towns with vintage neon signs and classic diners, crossing into Missouri near St. Louis, home of the Gateway Arch.

Through the Heartland to Oklahoma and Texas

Kansas offers the shortest segment of the route, just a few miles, before you cross into Oklahoma’s long stretch of original pavement and into the Texas Panhandle, where Cadillac Ranch is a reliable photo stop.

Across New Mexico and Arizona

New Mexico and Arizona hold some of the most scenic and historic sections, including Petrified Forest National Park and the restored stretch of road through Seligman, Arizona.

Finishing in Santa Monica

The route ends at the Santa Monica Pier, marked by an “End of the Trail” sign that’s become one of the most photographed spots on the whole drive.

Where to Stay and Eat Along the Way

Classic Motels, Diners and Roadside Icons

Part of the appeal of a Route 66 drive is the mid-century motels and diners still operating along the way. Booking ahead in smaller towns matters more than it does on a typical interstate trip, since some of these towns only have a handful of rooms available on any given night.

Balancing Big Cities and Small Towns

It’s worth mixing in a night or two in a bigger city, like St. Louis or Albuquerque, with the smaller-town stays that make the route feel authentic. That balance keeps the trip interesting without wearing you out.

Making the Logistics Easier

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If you’re planning a shorter drive first to get a feel for how the tools work, our guide to planning a Phoenix-to-Tucson road trip shows the same step-by-step approach on a smaller scale. And if Route 66 is just the start of your road trip plans, our road trips page covers itineraries across the country.

Final Tips Before You Hit the Road

Vehicle and Packing Checklist

Get your car checked before a drive this long, especially tires, fluids, and brakes, since some stretches of the route pass through remote areas with long gaps between service stations. Pack a paper map or offline route as backup, since cell service drops in parts of New Mexico and Arizona.

A US 66 road trip rewards a little planning with a lot of memorable stops. Once you’ve got your dates and rough route in mind, the rest comes down to deciding how many diners, ghost towns, and neon signs you want to fit in along the way.

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