Thanks to everyone who participated in the 2025 Guess The Route Contest!

Over three hundred entries were received in the 22nd (mostly) annual RAGBRAI Guess the Route Contest to pick the RAGBRAI LII towns. Although many of you correctly guessed that we would ride on the northern half of Iowa this year, only THREE of you guessed every overnight town.
Want to see how your guesses stacked up? See below for our most frequently guessed town analysis. Of the three people who correctly guessed the route, we randomly selected each podium standing.
Here are this year’s winners:
- 1st Place: Zeb Squires of Iowa City, IA
- Won $100 Gift Card to the RAGBRAI Shop
- 2nd Place: Robert Oliver of Ankeny, IA
- Won $80 Gift Card to the RAGBRAI Shop
- 3rd Place: Jeff Lee of Oregon, WI
- Won $60 Gift Card to the RAGBRAI Shop
Zeb Squires of Iowa City, Iowa was the big winner. Zeb picked right on all eight towns: Orange City, Milford, Estherville, Forest City, Iowa Falls, Cedar Falls, Oelwein, and Guttenberg! Bonus points for spelling each town name correctly. When asked to comment on his big win, Zeb said:
“I’d like to thank RAGBRAI for making what is always my favorite week of the year. It’s a fantasy camp of fun and freedom – biking, camping, cooling off in pools and ponds, sampling local food, loitering under rural shade trees, and meeting fellow riders and the great people of Iowa, and out drinking them in small town bars. A down year of RAGBRAI is still better than being in the real world.”

Stats
- With 137 guesses, Dubuque was our most frequently guessed town that we will not be visiting in 2025. Sorry about that! Dubuque is geographically close to some of our 2025 Overnight Towns so that was a great guess.
- The most guessed 2025 Route Town on the correct day was Orange City with 46 guesses. Guttenberg was the next best guessed with 40 correct guesses. And Forest City was the third most guessed at 38 correct guesses on the correct day.
- The least guessed correct town was Oelwein, and we also learned that Oelwein is difficult to spell correctly.
- The most predicted incorrect route was: Sioux City, Cherokee, Algona, Clear Lake, Manchester, Dyersville, and Dubuque. Just missing one town so take notes for 2026, Matt Phippen!
A down year of RAGBRAI is still better than being in the real world.”
Zeb Squires
How do this year’s RAGBRAI Guess the Route results compare with previous contests?
2003 – Winner guessed 7 towns
2004 – Winner guessed 7 towns
2005 – Winners guessed 5 towns
2006 – Winners guessed 3 towns (wow, we stumped you!)
2007 – Winner guessed 5 towns
2008 – Winner guessed 6 towns
2009 – Winner guessed 8 towns (perfect!)
2010 – Winner guessed 6 towns
2011 – Winner guessed 6 towns
2012 – Winner guessed 5 towns
2013 – Winner guessed 6 towns
2014 – Winner guessed 5 towns
2015 – Winner guessed 5 towns
2016 – Winner guessed 7 towns
2017 – Winner guessed 6 towns
***GTR Hiatus/Incomplete Records***
2023 – Winner guessed all 8 towns (perfect!)
2024 – Winner guessed all 8 towns (perfect!)
2025 – Winner guessed all 8 towns (perfect!)


