Route 66 Word Search: Free Printable for Its 100th Birthday

Somebody at your table drove Route 66 in a station wagon with no air conditioning, and they have been waiting decades for someone to ask about it. The highway's 100th birthday on November 11, 2026 is a good excuse to ask.

This Route 66 word search packs 16 towns and roadside words from Illinois to California into a shield-shaped grid. Play it at the top of this page, print the same puzzle for the kitchen table or the activity room, and use the trivia below to get the stories started.

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What is in this Route 66 word search?

This Route 66 word search hides 16 words: eleven towns along the old road and five words that capture its roadside culture. The towns run in driving order from east to west, so solvers can trace the trip on a map as they find each one. On medium, words run across, down and diagonally downward.

Kansas is the eighth Route 66 state and the easiest to miss: the highway crossed only about 13 miles of its southeast corner, through towns like Galena and Baxter Springs. That makes a good trivia question on its own.

Why is Route 66 turning 100 in 2026?

Route 66 turns 100 because U.S. Highway 66 was established on November 11, 1926, when the numbered federal highway system was approved. It became the main road west for travelers heading from the Midwest to California, and towns along it grew up around gas stations, diners and motor courts.

The road was officially removed from the U.S. highway system in 1985 after interstates replaced it, but much of the old alignment is still drivable and marked "Historic Route 66." The National Park Service Route 66 travel guide lists more than 100 historic places along the route, many of them listed on the National Register of Historic Places.

• Established: November 11, 1926.
• Length: about 2,448 miles.
• Ends: Chicago, Illinois, and Santa Monica, California.
• States: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.
• Nickname: "The Mother Road," from John Steinbeck's 1939 novel.

What Route 66 trivia questions work for families and seniors?

The best Route 66 trivia mixes geography, music and roadside landmarks, so younger solvers can guess and older ones can remember. Read the questions aloud after the word search is done and let whoever drove the road act as the judge.

• How long was Route 66?

  About 2,448 miles, from Chicago to Santa Monica.

• Which state has the shortest stretch?

  Kansas, with about 13 miles.

• Who wrote the song that tells you to get your kicks on Route 66?

  Bobby Troup wrote it in 1946, and Nat King Cole's recording made it famous.

• Where can you see ten cars buried nose-down in a field?

  Cadillac Ranch, on the edge of Amarillo, Texas.

• Which Oklahoma landmark is a big blue whale?

  The Blue Whale of Catoosa, a swimming-pond landmark near Tulsa.

• Which national park in Arizona has petrified wood along the old road?

  Petrified Forest National Park.

For senior centers, the questions are only the opening. Follow each one with "Did anyone stop there?" and give the conversation room. Road trips, family cars and the first motel with a pool are memories many residents love to share.

How do you make your own Route 66 puzzle?

Make your own by picking the stretch that matters to your group, typing those towns into the free word search maker, and printing it with an answer key. A class in Oklahoma might use only Oklahoma towns, while a family planning a trip can list the stops on their own route.

1. Choose 12 to 16 words. Mix towns with roadside words like DINER, MOTEL and NEON so the list is not only place names.
2. Keep words to one piece. A two-word name runs together (SANTAMONICA), so a single word like PIER is often easier to spot.
3. Set the difficulty. Easy runs words across and down, medium adds diagonals, and hard adds backward words.
4. Download the PDF with the answer key and print one per person.

Want more than one format? The same town list works as a Route 66 word scramble for the car, and the Worksheet Builder can put a word search, a scramble and a maze on one "road trip" page. The shield-shaped grid in the companion puzzle comes from the word search maker's shaped grids, a Premium feature included with the Day Pass and Plus.

For the drive home, the daily Connections puzzle is a good passenger-seat game: four groups of four, solved out loud.

Frequently Asked Questions

When is the Route 66 100th anniversary?

The anniversary is November 11, 2026. U.S. Highway 66 was established on November 11, 1926, and towns along the route are holding centennial events throughout the year.

What towns are in the Route 66 word search?

The puzzle includes Chicago, Springfield, Joplin, Tulsa, Amarillo, Tucumcari, Albuquerque, Gallup, Flagstaff, Kingman and Barstow. It adds five roadside words: highway, diner, motel, neon and roadside.

Is the Route 66 word search good for seniors?

Yes. The words are familiar place names, and the topic invites memories of road trips. For bigger print, enlarge the page on a copier or use the large print word search option.

Can I print the Route 66 word search for free?

Yes. The companion puzzle downloads as a PDF with its answer key, and the free word search maker lets you build your own version from any list of towns.