Trip Planning FAQ Chicago to Springfield Springfield to St. Louis

Thinking about taking your own trip on Route 66? Excellent! It really is the "highway that's the best." While I recommend that you consult with more expertly written guides than this one (my favorite is Jerry McClanahan EZ66 guide, which I'd augment with David Wickline's Images of 66; also check out Ron Warnick's Route 66 news) I hope to offer some useful advice that will save you some hassles before you hit the road. To allow some flexibility, I've written this guide in FAQ form (note: some of the questions are inspired by Tom Snyder's Traveler's Guide and Roadside Companion, which aided my family's first trip in 1996). While I also maintain a blog-page entitled Route 66 Travel Advice, which I may update from time to time, the page you're now reading is where I recommend that first-timers start...

When should I go?

I've yet to travel large sections of Route 66 in the fall -- and winter driving can be treacherous, even in New Mexico and Arizona. So let's focus on spring and summer. My preference is spring: traffic and crowds are diminished and the price of lodging is a little lower. My 2008 trip was from March 21st through March 31st, and it was delightful, mostly. While you can count on blue skies and sunny days out west, you're likely to confront a mix of precipitation ranging from rain to snow from Chicago through Oklahoma. Flooding and washed out surface roads are also a possibility. So keep an eye on the weather and ask locals about road conditions up ahead. Summer brings more clear skies but also some wicked heat, and not just in the Mojave Desert. If you drive during that season, watch your engine temperature, try to avoid overdoing the air-conditioning, and keep yourself hydrated. In both seasons, though, evenings can get cool, so dress in layers.

How long will it take?

Sticking to interstates, you can do the trip in three or four days. But why would you? This answer assumes that you're focusing on the Mother Road. While Tom Snyder's guide offers a much more nuanced trip-time calculator, I'll suggest that you can do the entire trip alone in nine days. Add a day or so per person (to account for individual passions that you might otherwise bypass) and add a couple of days each for excursions away from Route 66 to visit places like the Grand Canyon or Las Vegas. This estimate also assumes that you're not trying to take every alignment of the old road. While purists will surely disagree, I don't think you should feel guilty for driving the interstate for stretches when 66 becomes a frontage road. And sticking solely to the Mother Road in Chicago, St. Louis, Oklahoma City, and Los Angeles requires more patience and knowledge of local idiosyncrasies than I can muster. In those cities, I mix and match surface streets and interstate connectors, and I think I travel more happily as a result. So, presuming the above, start with nine days and take it from there.

How carefully should I plan?

Enjoying Route 66 is all about serendipity. Allow yourself to converse with a chatty owner of a mom and pop motel, eat an extra large piece of homemade pie at a greasy spoon, take enough time to compose a good photograph of a neon sign at twilight, and don't worry too much about "making time." The worst thing you can do is arrive in a wonderful place like Seligman, Arizona, meet a cool fellow like Angel Delgadillo, and rush off because you made reservations at a motel down the road. If you know that you'll arrive in a certain town within a couple of hours, you might consult the National Route 66 Federation's Route 66 Dining & Lodging Guide and reserve a room by calling ahead. But it's also fun just to cruise the main drag in search of a neon sign that speaks to you (presuming that you follow your instincts for safety's sake). That being said, there are some places that require reservations long in advance; choosing them will require you to trade some flexibility for a sure thing. So, if you must sleep in a cement teepee, don't plan on just dropping by the Wigwam Villages in Holbrook or Rialto. These places are popular and fill up fast. I also was glad that I reserved a room at La Posada in Winslow. It's pricy, but worth the time and money to plan ahead. And I don't have to tell you that Grand Canyon campsites fill up months in advance. Use your best judgment in these places. Just don't calendar every three hours of your trip, and you'll do just fine.

How much does it cost?

That's hard to estimate. I recommend setting up a budget and adding one-third. Then you won't be as upset when you exceed your estimates anyway, which you will. Even so, big-picture budgeting relies on too many imponderable variables. What's your preference? Taco Bell bean burritos every day or the only cloth napkin-place in a one-stoplight town? Dusty, moldy no-tell motel or B&B with doilies and decanters of sherry? And then there's transportation. Are you renting a car one-way? That'll cost ya. Shipping your motorcycle over from Germany? Dinner's on you, then.

Rather than try to answer that big question, let me tell you some smaller specifics. My most inexpensive motel (The Desert Hills in Tulsa) cost 42 bucks. My priciest choice (La Posada in Winslow) ran 110 bucks and change. Food costs ran the gamut from none (not a wise choice for breakfast) to a final sit-down meal with a decent single-malt to celebrate reaching Santa Monica: about 40 bucks. Gas ran between 33 and 40 bucks a fill-up, which I averaged about once a day. Prices hadn't reached four bucks a gallon, but at the time of this writing, I wouldn't be surprised to see that number topped pretty soon.

Oh, but here's the best way to avoid excess cost. It's simple: Don't speed. Speeding is lousy for gas mileage, and small-town cops generally aren't impressed that you're whizzing through their communities, "seeing America." Disrespecting local speed ordinances in your shiny new rental car can really wreck your day. So don't do it.

One other thing, all those strange expenses from different states may cause your credit or debit cards to get flagged for potential fraud, so contact your bank and let them know where you're going and when. That way there's a higher chance that when you need to sign for those cool Route 66 t-shirts, the machine won't make some horrible beeping sound.

Is it safe?

Route 66 takes you through some of the nicest small towns and friendliest big cities in America. And you certainly want to be open to pleasant conversations with strangers without appearing too rushed to get back into the confines of your car. But you'll encounter the risk of crime along the highway like you will anywhere else. On our first trip in 1996, someone broke into our car while we were playing a game of miniature golf in St. Louis, and the jerk stole Jenny's purse. That was back when we carried cash for our trips (hard to imagine now, isn't it?). The loss was relatively small, but the wound to our sense of safety stung for days. And since the outskirts of some bigger cities are surrounded with pockets of genuine economic despair, the threats of theft or violence cannot be ignored. My advice applies equally wherever you go: Know your surroundings, trust your instincts, and keep a mobile phone handy. Ultimately though, whether in a big city or in a small town, it's best to remember one immutable fact of human nature: most people are basically good.

So that's my advice on traveling Route 66. It's a wonderful trip, a chance to create happy memories and meet people you'll never forget. If you're new to long distance road travel, start with a short alignment through Missouri or Oklahoma. See if you get your kicks then. Afterward, plan to do the whole thing, from Chicago to LA. When you do, email me your Route 66 travelogue! [Continue...]

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All text and photos copyright Andrew Wood