How Long Does It Take?

How Much Time Should You Take to Drive Route 66?

Neon sign at the Best Western Route 66 Rail Haven in Springfield, Missouri

The ideal way to see Route 66 would be an open-ended trip with unlimited time. Strike out from Chicago, go as far as you like each day, and start looking for a place to stay at the end of each day.

But for most of us this is impractical. Few of us have unlimited time. And unless you’re willing and able to drive your own vehicle to Chicago and drive it home from Los Angeles, you’ll need to book flights and a one-way rental car in advance. That means you’ll have to decide in advance how much time you want to spend on your Route 66 road trip.

Plan on at least 3 weeks for the whole trip. Route 66 is so long—around 2300-2400 miles—that a Route 66 road trip is roughly equivalent to driving all the way across Europe AND the Middle East. You cannot do this trip in one week—well, you could drive it, but you won’t have time to see anything along the way. Two weeks is recommended by a lot of experts, and it’s doable, but you’ll have time to see only a few sights along the way. Route 66 is an ideal opportunity for what some travel experts call slow travel. You’ll need at least 3 weeks to do Route 66 justice, and even then you probably won’t see everything you want to. Historic66.com agrees with this, recommending 3 weeks to a month for the whole trip.

Don’t plan to drive more than 3-4 hours a day. That leaves time to stop and see several sights along the way, as well as a lunch break and restroom breaks. Also, we found that driving Route 66 is more tiring than jumping on an interstate. You’re always on alert, looking for the next turn, and there are stretches where turns come up every few miles. So consider planning to drive less each day than you normally do on road trips.

To estimate driving time using Google Maps, pick a segment of Route 66 (say, Springfield, Illinois, to St. Louis, Missouri). Enter the starting point (in this example, Springfield, Illinois) and destination (in this case, St. Louis). Click on the three dots in the upper right corner of the app (at least, this is how it works on an Android) and choose “Route options.” Check “Avoid highways” and “Avoid tolls.” This will give you a route that’s probably mostly along Route 66—close enough for a good estimate on driving time.

Plan on just a few stops each day (not counting meal stops). As I’ve said, you won’t be able to stop to see everything. Figure out the kinds of things you most want to see—my page on setting priorities can help. Then choose just a few top-priority stops each day. If you find that you have time and energy for more stops, great, but this way you won’t miss anything you’re really looking forward to.

Plan on no more than 2 or 3 lengthy stops each day—those that can take an hour or more—such as:

¨  Walking around small towns or on trails

¨  Visiting museums

¨  Detouring off Route 66 to see something in the region

Other stops may not take an hour, but aim to limit them too, as they can add up. You may spend just 15 minutes chatting with someone you meet along the way or browsing a gift shop, but if you do those things more than once, they’ll take a chunk out of your day.

Then there are photo stops. There are so many sights along Route 66—several dozen each day—that just stopping to jump out of the car for quick photos of them all can add up to a surprising amount of time. Some photogenic spots are along roads or highways with no shoulders, so you’ll spend additional time just looking for a place to pull over and walking to the spot to take a photo. We played photo stops by ear, stopping to photograph only those sights we thought were especially cool, unusual or distinctive. Everything else we simply waved at as we drove by. We figured there are plenty of online photos we can access if we want to.

Include a few no-travel days. Let me repeat: a Route 66 road trip is pretty intense—you’re finding and seeing tons of new things every day. So, every third or fourth night, take a break and stay two nights at the same place and recharge. Spend those nights in towns or cities where you’d like to do in-depth exploration. On our trip from Chicago to Tulsa, we stayed 2 nights in St. Louis and 2 nights in Tulsa. We spent those days seeing some of the sights in those cities and just relaxing.

Allow time to travel between home and the beginning and end of Route 66. Route 66 is (duh) a one-way trip. You have to allow additional time to get to Chicago and go home from Los Angeles (or vice versa). If you’re driving your own car instead of flying, just getting to and from each end of Route 66 can add several days to the trip, depending on where home is.

You don’t have to drive the whole thing in one trip. We decided to tackle Route 66 in three separate trips: one from Chicago to Tulsa, one from Tulsa to Albuquerque, and one from Albuquerque to Los Angeles. If you can afford three sets of flights instead of one, I highly recommend this. We allowed 7½ days to travel from Chicago to Tulsa, plus a half day to fly to Chicago and a day to fly home from Tulsa. It was a great trip and left us eager for the second leg. In retrospect I wish we’d allowed 8 or 9 days—we would have liked time for a few more stops. But otherwise this worked out well. An added bonus: we weren’t tired of road-tripping when the first leg ended—we were eager to return and tackle the next leg. If you’ve never done this kind of road trip before, doing just one segment is a great way to find out if you like it before committing to a lengthy road trip that you might find yourself enduring rather than enjoying.