Puzzle Road Trip: Route 66 is a puzzle book featuring a variety of easy-to-medium puzzles themed after the most famous highway in American history — Route 66. Puzzles include twists on classic favorites like word searches, sudoku, story logic puzzles, mini crosswords, and more. The book flows from the eastern terminus in Chicago, Illinois to the western terminus in Santa Monica, California, with a plethora of details about the historic route and the people, places, and attractions along the way.
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For a list of planned retailers, see below.
All materials in and associated with Puzzle Road Trip: Route 66 are © 2025-2026 David Millar. All rights reserved.
Route 66 runs from Chicago, Illinois to Santa Monica, California, passing through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.
Route 66 was a numbered U.S. highway that was designated in 1926. Over the years, the route was modified, re-routed, tweaked, truncated, bypassed, and eventually decommissioned in the 1980's.
Its legacy made a lot of folks eager to preserve the spirit and story of the highway for future generations. Some states designate the path of Route 66 (or a close equivalent) as a scenic route, byway, or a specific state route, like parts of Oklahoma state route 66. The route is also used as the basis for U.S. Bicycle Route 66, as part of the U.S. Bicycle Route network.
NO! It bother's Dave's OCD to no end that someone opened a Route 66 gift shop in San Francisco.
Parts of the original route can still be driven. Other parts cannot for a variety of reasons, including but not limited to: abandonment, destruction, reuse as a private drive-way, and conversion to bicycle-only and/or walking-only paths. Other parts are still able to be driven, but have been converted to modern highway standards.
This is a very subjective question, but most folks agree you should spend at least two weeks to get the best experience. It's impossible to see and do everything, though, so the best advice is to do research on the parts you want to see the most and plan around those.
Yes, but parts of the road in western Arizona have sketchy switchbacks and it's quite tricky to navigate those with a larger vehicle. For that stretch, it's best to take an alternate route and backtrack with a smaller car or some alternate method.
No, it's nearly impossible to drive the historic route with signage alone. Since the highway was officially decommissioned, the signage along the route is maintained by each state individually and can vary quite a bit in style and quality. Additionally, the numerous spurs, alternate alignments, and repurposing of the highway can lead to confusing navigation and get you off-track quite easily. Most importantly, the highway being as famous as it is lends itself to folks slapping stickers on the signs or even stealing signage as a souvenir, so the signs may be illegible or missing altogether. It's better to have a GPS or navigation app available as well as a dedicated book or map for navigating in areas with low signal.
Probably not. For the most part, the route does not overlap any major tollways and can be navigated without encountering them.
If you plan to do a mix of actual Route 66 roadway and some modern highways, you may encounter tolls in Illinois and Oklahoma.
For Illinois, you can go to the Illinois Tollway website and register your license plate to pay online, which is recommended if you do not already have a transponder and do not plan to drive in areas where one is needed in the future.
For Oklahoma, the Oklahoma Turnpike Authority can bill you by mail via your license plate, but it is more expensive than if you register ahead of time and obtain a Pikepass. Oklahoma also interoperates with nearby states, so drivers from Texas and Kansas should check to see if you already have a tag that works with Oklahoma's turnpikes for automatic billing.
If renting a car for your road trip, your best option is to check with your rental company for terms and conditions related to toll roads and set your navigation app to avoid toll roads when able.
So far Dave has only driven a little over half of Route 66 — mostly the eastern half — mostly covering sections from Chicago, Illinois through Santa Fe, New Mexico. Some of his favorite places along the route include:
The print version of the book isn't available yet, but Dave hopes to get it into some of the shops along the way for enjoying on your road trip, either as a passenger through the quieter parts, or after hours in your motel room or the back of the RV. If you work with or own a shop along Route 66 and would be interested in carrying the book, please e-mail Dave for information!
The following shops plan to carry the print edition when it's available:
Dave is not a travel agent or expert and makes no warranties about the accuracy of the information shared above. The information is subject to change, and updates will be provided when known and feasible.
Puzzle Road Trip: Route 66 was designed and composed in Inkscape, a free and open-source vector graphics editor similar to Illustrator. Special shout-out to Martin Owens who has spruced up the PDF support in Inkscape over the last several years, which has benefitted both this book and the puzzles here on The Griddle.
The book uses signage shapes found in and/or derived from the Manual on Uniform Traffic Control Devices (MUTCD) from the U.S. Federal Highway Administration, including U.S. highway shields, Interstate highway shields, and some arrow shapes.
The book contains a map of the United States with Route 66 drawn over it, which was derived from an image in the public domain on Wikimedia Commons by user SPUI~commonswiki.
The book's primary typeface is Overpass, designed by Delve Fonts, inspired by Highway Gothic, and sponsored by Google Fonts and Red Hat.
The book's secondary typeface is Barlow, designed by Jeremy Tribby, and it looks great as a license plate font.
The book also uses the typefaces League Gothic and Libre Barcode EAN13 on the front and back covers respectively.
A big part of the history of Route 66 is that it was bypassed by the interstate highway system, and small towns full of working-class folks got short-changed and left behind. I believe that generative AI is doing the same thing today with art and programming, and as someone who works with both, it's disheartening to see. Puzzle Road Trip: Route 66 was made without the use of generative AI, being written by hand in graph paper notebooks, graphics drawn by hand in Inkscape, and word puzzle clues being written and checked by hand as well. The book is a labor of love, not the result of prompting an LLM.
Huge, massive thank-you to the folks that helped with test-solving to get this book into shape: