Lollapuzzoola
Lollapuzzoola is a crossword-solving tournament held annually on a Saturday in August. Founded in 2008 by Brian Cimmet and Ryan Hecht, it is the second-largest crossword tournament in the United States, and the only major tournament in New York City. The term "Lollapuzzoola" was coined by Amanda Yesnowitz, as a play on the Lollapalooza music festival. Lollapuzzoola 18 took place on August 9, 2025, and was cohosted by Brian Cimmet and Brooke Husic.
For its first three years, Lollapuzzoola was held at the First Methodist Church in Jackson Heights, New York, but owing to its increasing popularity, in 2011 the tournament moved to All Souls Church in New York, New York. In 2018, the tournament relocated again, still within New York City, to Riverside Church.
Lollapuzzoola typically consists of a main slate of five themed crosswords followed by a championship final puzzle in two skill divisions. There are many other games and puzzles throughout the day, including a pre-tournament social mixer, a multi-crossword meta suite, and a variety puzzle suite. Puzzles are commissioned by the tournament, and are designed to fit a full-day theme, giving the tournament a certain unity. Themes have included Theme Park, Sweet 16, Television, and The Olympics. Crossword constructors who have contributed to Lollapuzzoola include Erik Agard, Brendan Emmett Quigley, Peter Gordon, Patrick Berry, Ashish Vengsarkar, Dan Feyer, Doug Peterson, Mike Nothnagel, Tony Orbach, Barry C. Silk, Elizabeth C. Gorski, Karen M. Tracey, Byron Walden, Andrea Carla Michaels, Deb Amlen, Matt Gaffney, Joe Krozel, Neville Fogarty, Patrick Blindauer, Joon Pahk, Aimee Lucido, Zoe Wheeler, Kevin Der, and Tyler Hinman.
Lollapuzzoola and its founders are discussed in David Astle's book "Puzzled." Lollapuzzoola has also been frequently mentioned on the weekly crossword podcast Fill Me In, which is cohosted by Cimmet and Hecht.
Four times during Lollapuzzoola's history, New York Times crossword editor Will Shortz purchased puzzles commissioned for the tournament for publication in the newspaper. On September 5, 2009, Mike Nothnagel's final puzzle from Lollapuzzoola 2 was published in the New York Times. On August 20, 2011, Byron Walden's final puzzle from Lollapuzzoola 4 was published. On September 11, 2014, Patrick Blindauer's puzzle "Change of Heart" from Lollapuzzoola 7 was published. On August 9, 2016, Andrea Carla Michaels's puzzle from Lollapuzzoola 4 was published in advance of the upcoming tournament, and as a promotion of Lollapuzzoola. Each time, an additional block of text was added to the puzzle to tell solvers that this puzzle had appeared in a national tournament and to give information about the winner and their solving speed. In the case of Walden's puzzle, the byline was extended to include "edited by Brian Cimmet and Patrick Blindauer", the first instance of an editor besides Shortz since he began working for the Times.
Mark Goodliffe, a British puzzle solver who broadcasts on his YouTube channel "Cracking the Cryptic" solved a Lollapuzzoola puzzle online in 2021. Wyna Liu discussed one of Lollapuzzoola's puzzles at length in her article "The Loading... Puzzle" in 2022. Hayley Gold wrote about Lollapuzzoola 15 in her article "A Crossword Tournament Returns to NYC for its Quinceañera" in 2022.
Participants and divisions
Anyone can participate. There are two skill divisions, a rookie division, a pairs division, and for those who can't attend in person, an at-home division. Prizes are awarded in all divisions, with trophies and cash/gift certificate prizes for the top winners in the two skill divisions. For the purposes of prizes contestants compete simultaneously in all divisions for which they are eligible, with no more than one cash prize per contestant.Format
The tournament consists of five rounds, each with a puzzle that all competitors solve. There are three rounds in the morning and two in the early afternoon. Puzzles vary in size and difficulty from round to round. The puzzles are commissioned by the tournament directors from the top constructors in crosswords, with the fourth puzzle the hardest of the set. The puzzles vary in size, shape, and difficulty, although the first one is traditionally a relatively easy 15x15 grid. The puzzles are always themed, and frequently themed in off-center, wacky ways not commonly seen in newspaper-published crosswords. For example, puzzles have included a "Name That Tune" gimmick; a post-solve Twister game; a puzzle that instructs the solver to eat a Chips Ahoy cookie upon completion; and a puzzle that required the entire room of solvers to make noises from their chairs, and thus perform an impromptu rendition of John Cage's 4After these five rounds, the top three solvers in the two skill divisions progress to the final round, which consists of solving a very difficult crossword on an oversize grid onstage at the front of the room. The competitors in this round wear noise-blocking headphones. The solvers hold a sheet of clues and write their answers on the grid with a dry-erase marker for all to see. The competitors are ranked by fewest mistakes, then time. The winner of this round is declared the champion. The top three competitors in the Express and Local divisions compete on the same puzzle with different sets of clues for their titles.