Here’s what I recommend for understanding, finding and experiencing Route 66 if you are a first-time traveler.
First, get the historical and emotional perspective on Route 66 with this excellent book: Route 66: The Mother Road 75th Anniversary Edition. Soak in the history of the road and the people and establishments associated with it.
As a first requirement for navigation, you need an overview map for each day’s driving, with a bird’s eye-view of a large stretch of the route, names of towns at a glance, and interesting stops highlighted. For this, use this set of eight maps (one for each Route 66 state): Here It Is! The Route 66 Map Series. These are large, hand-drawn, very high-level maps that show the route on a gross level. You can clearly see that the route runs mostly parallel to the (five) interstates that replaced it. Visually, the only aid these maps provide for staying on the route are indications of which side of the interstate the route is on at any given place. But the text alongside each map gives turn-by-turn directions. You will have a very, very hard time getting by on those directions alone. Do not use these maps for turn-by-turn directions.
For turn-by-turn directions, use the very excellent book EZ66 GUIDE For Travelers – 2nd Edition. This is a spiral-bound book of detail maps for the entire route. This is the book you need to stay on Route 66. This book and the set of maps I mentioned above are complementary. Refer to the set of maps to track your overall progress and foresee what the next few hours have in store for you. Use the detail maps to navigate and get exhaustive information on what to do and see every few miles. Don’t consider doing your trip with just one of these resources; you need both.
Finally, get this nice picture book of things to do, see, learn about and experience on the route: Route 66 Adventure Handbook: Expanded Third Edition. Flip through this book before your trip and at the start of every day, and keep it handy as you drive. Stop when something catches your fancy!
With these books and maps, you have a wealth of information on where to stop and what to do. This amount of information is overwhelming if your goal is to distil the few mandatory attractions that you would feel ashamed to inadvertently miss. You might want to consider investing in something like AAA Route 66: The Best of the Mother Road, a fold-out map of Route 66 attractions considered by some to be must-dos. This map condenses the route to a bunch of “ooh-aah” pit-stops accessible from the freeway, but it’s still useful as a small, manageable list of highlights you probably won’t want to miss along your journey.
Keep a GPS stashed away in your glove compartment ready for emergencies; there is no need to have it powered on and available for reference all the time. Get lost a few times and find your way back using your maps, books and luck! Or decide not to find your way back right away! It’s part of the experience of following this grizzled old road.