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Delving into the Lollapuzzoola 19 Puzzles!

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The nineteenth edition of Lollapuzzoola, as is tradition, arrived on a Saturday in August. Last Saturday, in fact. (I was not in attendance, but I did purchase the Solve at Home puzzle pack.)

I had a chance to sit down and try my hands at this year’s tournament puzzles, and I was certainly not disappointed.

This year’s theme was “Around the World.” Every puzzle had something to do with travel or geography, and the constructors were clearly inspired in all sorts of ways. Let’s take a look at what they came up with.

Warmup Puzzle A: Twinlets by Brian Cimmet

A traditional Cimmet Twinlets (Cimlets? CimTwins?) puzzle begins the day’s proceedings and boy, did he hit the ground running! He presented the solver with two identical grids and two sets of clues, and you have to figure out which grid each answer applies to.

This was complicated by the fact that EIGHT of the answers across both grids had the same clue: “European country.” But I started filling in answers to establish the first grid, then worked back and forth as the answers continued to populate and reveal which clues fit which grid.

I really dig Twin Crosswords or Twinlets puzzles, and Brian has a knack for putting just enough common letters in the same spaces in both grids to keep you guessing. (And for writing several long clues that never disappoint.) I thoroughly enjoyed this puzzle.

Interesting grid entries included LOST ART, SILENT O, and O, CANADA, and my favorite clues were “Three-syllable berry that’s great for both health and crossword construction” for ACAI and the 39-Across pairing of “____ on the Roof” for FIDDLER and “The other 39-Across, for one” for MUSICAL.

Warmup Puzzle B: Up in the Air by Brooke Husic

With a grid layout that feels like a moth or butterfly in flight, Husic clearly had flying on the brain, and her travel-centric apt pair — JETLAGGED and FLIGHT DELAYED — stacked together nicely. (Heck, having a grid that was short in one direction and long in the other FELT like travel, the trip there and the trip home.)

Brooke is a master at maximizing smaller grids, and she paired fun grid fill with longer, trivia- and opinion-focused clues, many of which continued the travel theme. (Also, she shouted out the board game Sky Team, which is a blast.)

Interesting grid entries included ALT LIT and JINX, and my favorite clues were “…—…” for SOS and “Plucked bass?” for ANGLED. (Though I didn’t know that pets can ride on Amtrak if they’re under 20 pounds. I love learning things from puzzles!)

There was also a contest puzzle featuring locations from famous musicals, which definitely tested my theatrical knowledge.

I’m sure there was frantic Googling during the breaks between puzzles for solvers to complete this one before the Puzzle 5 deadline!

Puzzle #1: Screen Sharing by Ada Nicolle

Kicking off a day of tournament solving is a daunting challenge — balancing accessibility, difficulty, style, flavor, skill, and playfulness, all while ably representing that event’s energy or that year’s theme — and I’m always impressed by the constructors who tackle that challenge.

Fortunately, solvers and tournament organizers were in the capable hands of Ada Nicolle, who created a great opening puzzle. It was a smooth solving experience with engaging cluing and tons of personality (as one should expect from Nicolle).

The theme was impressive, featuring compound words or phrases where both parts of the answer could be placed in front of the word CHECK to form a common phrase (RAIN check and COAT check for RAINCOAT, for instance), ably showing off the PRE-CHECK promised by the revealer.

Interesting grid entries included NU METAL, HO-HOS, TONSIL, and BAGUETTE, and my favorite clues were “What it might take to ask out a crush” for COURAGE and “Wide-brimmed accessory for Carmen Sandiego” for HAT.

Puzzle #2: Wherever the Wind Takes You… by Carina da Rosa

This year, the ORCAS crowned Carina as an Emerging Constructor to watch, and I think she’s proven everyone who voted for her correct.

The eye-catching shape of a hot-air balloon grid was just the tip of the iceberg with this puzzle, as solvers would discover that one letter from each theme answer had floated up, up, and away from the main entry, appearing in a circle above as part of the balloon’s design. The capper was each letter spelling out HOT AIR.

This is beautiful design and execution, especially with a packed grid like this. The page itself was equally packed with longer clues which made it a little difficult to read and solve (a pattern that would continue with the next puzzle… or maybe I need to revisit my prescription with my eye doctor). Nonetheless, this was a highlight of the day.

Interesting grid entries included RAW OYSTER, UNSUNG, COLBERT, and ADROIT, and my favorite clues were “Place to park your butt?” for ASHTRAY, “Hoffman whose FBI file was 13,262 pages long” for ABBIE, and “Portuguese greeting formed by dropping one letter from a Spanish greeting” for OLA.

Puzzle #3: What to Know Before You Travel by Amie Walker

Intend your puns indeed, as Amie Walker has some doozies for you in this one! The clues take traditional travel terms (“Baggage claim,” “Carry-on item,” “Domestic carrier,” etc.) and deliver tongue-in-cheek responses as answers (I’VE GOT TRUST ISSUES, TEMPER TANTRUM, BABY STROLLER).

Packing seven answers into this grid was no small feat, but Walker managed to stack the grid with charming fill as well, offering the densest and most ambitious puzzle design of the day. My puzzly mind definitely appreciated this one, even if my eyes didn’t.

Interesting grid entries included BLITHERING, ICE CAVES, EGG CUP, and COBBLE, and my favorite clues were “Word ____ (you, maybe)” for NERD and “Enjoy a Manhattan tour, say?” for BARHOP.

Puzzle #4: Crossing the Line by Adam Wagner

Much like the dreaded Puzzle #5 at the American Crossword Puzzle Tournament, Puzzle #4 at Lollapuzzoola is usually a super-heavyweight challenge, and this might be the toughest I can remember from any previous event.

It took me a LONG time to realize the trick of this one. The revealer DAY OFF pointed me towards some sort of time shift, but I kept staring at the entries that crossed the dotted line down the middle of the grid and coming up empty. Seven of the clues simply refused to match their entries, until I finally noticed that each of those seven clues started with same letter as a day of the week (“Mob target” for Monday, “Tutor coaches” for Tuesday, etc.)

And when you shift the first two letters of each clue back a day, the clues suddenly make sense. “Mob target” becomes “Sub target,” which makes total sense for DESTROYER.

Tough clues, TOUGH gimmick, but a well-constructed puzzle. Although I easily completed it within the 40 minutes allowed, I don’t know that I understood it during that 40 minutes.

Interesting grid entries included RUH-ROH, U-HAULS, SAMURAI, and FROYO, and my favorite clues were “Beat generation?” for PULSE, “Breakfast accompaniment?” for BED, and “Construction term that becomes a meteorological term if SO is added after the first letter” for IBAR.

Puzzle #5: Every Second Counts by Will Nediger

Nediger closed out the pre-championship puzzles with this grid that feels like one long, snaky journey from the upper left to the lower right, meandering like a river.

Solvers found a very cool theme waiting for them where the theme answer was one location, but another location was circled in alternating spaces within the theme answer, like ALGERIA (AGRA within ALGERIA). Will packed six of these pairings into the grid, plus the revealer ALTERNATE PLANS. (And I quite liked SIDE TRIP as sort of a bonus revealer.)

All in all, a very impressive bit of construction, research, and theme execution. A terrific closer before the big finale.

Interesting grid entries included IDEOGRAMS, PIPING HOT, TRIMARAN, CLARISSA, and Wario, and my favorite clues were “Like plants that produce little to no chlorophyll” for ALBINO and “Punishment from a Discord moderator” for BAN.

Puzzle #6: Championship Final by Trenton Charlson

As always, there were two sets of clues for the Finals puzzle, the Local and the more difficult Express clues. No matter which clues you were working with, you were in for an excellent tournament finale.

This grid had clean stacks of 8-letter entries and 9-letter entries in the corners, and some unforgiving crossings that really reminded me of how much skill and creativity it takes to construct a great themeless puzzle.

The cluing was surprisingly accessible for a championship final (across both the Local and Express clues), and I can imagine many of the solvers in attendance performing well on this solve.

I don’t know Charlson’s work, but I’ll definitely be looking for their byline in the future.

Interesting grid entries included JUMBO JET, SEE STARS, YTTRIUM, and DON QUIXOTE. Both the Local and Express sets of clues had some gems, so I’ll list them separately below:

Local clues:

  • “Farm animal follower” for EIEIO
  • “Festival celebrating the arrival of spring” for TET
  • “Starter starter?” for NON

Express clues:

  • “Agrarian refrain” for EIEIO
  • “Something a guitarist often has on hand?” for CALLUS
  • “One who dreams knightly?” for DON QUIXOTE
  • “Palms or pockets” for STEALS
  • “Start to sense” for NON
  • “9 to 5, e.g.” for ODDS

There was also a tiebreaker themeless midi by Laura Braunstein, which was an excellent, quick solve. The playful cluing and great flow made it an enjoyable interlude before the championship, and the apt pair of FIRST SIGHT and LAST RESORT really encapsulated the travel theme of the event nicely.

Interesting grid entries included WIGGLE ROOM and DARK HORSES, and my favorite clues were “Place for a pawdicure” for PET SPA and “General of the Resistance” for LEIA (put some respect on her name!).

There were ALSO two bonus puzzle suites — a variety one by Scott Weiss and a meta crossword one by Crossword Gentleman Doug Peterson — which I did not have an opportunity to solve before posting.

Another year, another parade of bangers from the Lollapuzzoola team. There were visually impressive grids, devious acts of cluing chicanery and cruciverbalism, and many many MANY trivia-loaded clues (a personal favorite of mine).

Every puzzle was well-constructed, smartly filled, and clued with love, personality, snark, and enthusiasm. It’s hard to precisely put a finger on what makes a crossword feel like a Lollapuzzoola puzzle — a unique blend of rock n’ roll and Tom Lehrer, maybe — but the LPZ spirit is alive (and often kicking) in each of these entries.

I can only imagine what they’ve got in store for us next year to mark the 20th edition of the tournament. Sadly, I guess we’ll have to wait and see.

On the plus side, I’ve got puzzle suites to solve while I wait! Happy puzzling, everyone!

Did you tackle this year’s Lollapuzzoola crossword tournament, fellow puzzlers, either from home or live in person? Let me know in the comment section below. I’d love to hear from you!

Lollapuzzoola 19 This Weekend (and More Tournaments Coming Soon!)

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Just a quick post today to talk about a puzzly event this weekend, two more coming up, and a brand-new one announced for next year!

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Lollapuzzoola always happens on a Saturday in August, and this Saturday, August 15th IS that Saturday in August.

Trenton Charlson, Carina da Rosa, Will Nediger, Ada Nicolle, Adam Wagner, and Amie Walker have constructed puzzles for this year’s event, “Around the World.”

(And those aren’t the only names contributing this year! Laura Braunstein constructed the tiebreaker puzzle, Crossword Gentleman Doug Peterson constructed the crossword meta suite, and Scott Weiss constructed the variety puzzle meta suite.)

There’s still time to sign up to compete from home! Click here for more details.

If you’re missing out on Lollapuzzoola, don’t fret. There’s another NYC puzzly event next month!

The 2026 Bryant Park Crossword Tournament returns on Saturday, September 19, with singles and pairs division solving available!

Mike Shenk has constructed all three puzzles for the event and will be co-hosting with Amy Goldstein, who is genuinely one of the nicest people in puzzles.

Click here for all the details!

Registration is open (and is nearly full, so sign up ASAP) for this year’s edition of the Midwest Crossword Tournament! Mark down October 3rd, 2026 on the calendar.

Shannon Rapp and Sally Hoelscher are organizing the tournament, and Christina Iverson and Tracy Bennett are signed up as editors, so you know the tournament is in good hands!

Click here for more details. Oh, and MWXWT merch as well!

2026 has been jam-packed with puzzly fun, and 2027 is looking just as bright. A new tournament will be debuting in March!

The Rain City Crossword Tournament brings puzzly challenges to the Pacific Northwest, as Seattle can now claim its own destination tournament!

Registration opens in early Autumn (I’ll keep you posted!) but you can click here for more details as the inaugural event approaches.

Will you be participating in any of these events, either in person or from home, fellow puzzler? Are you excited for a new tournament to be hitting the West Coast? Let us know in the comments section below! We’d love to hear from you.

The Results from the 14th ORCAS Awards!

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The ORCAS are the Oscars of the crossword community, dedicated to celebrating excellence in crosswords, and that was certainly the case during last night’s awards ceremony!

Clocking in at just under an hour, this was an event at breakneck speed, opening as all online award shows should: with technical difficulties.

David Kwong offered some anagram suggestions for other award shows and then passed the mic to Rich Proulx, whose bowtie game was ON POINT.

Rich’s intro was delightful, particularly when he shared that over $15,000 had been raised for the Trevor Project through the ORCAS puzzle packet!

With 97 people in attendance — including many nominees and puzzle luminaries in the chat — the first award was preceded by a tough trivia puzzle celebrating all of this year’s presenters:

After the solution was revealed, Ophira Eisenberg joined David in the hosting duties before inviting our first two guest presenters to handle BEST META CROSSWORD and BEST EASY CROSSWORD.

Aimee Lucido (author of Words Apart) read out the nominees for BEST META CROSSWORD.

I must confess that meta crosswords aren’t always my bag, but there’s no denying the skill and craftiness it takes to construct an effective meta. I ended up voting for “Blind Stitch” by Hanh Huynh because it felt like such a solidly constructed introduction to the concept of meta crosswords. It’s a great solve.

WINNER: Evan Birnholz for “Flying Colors”

“Queen of the Mondays” Lynn Lempel then read out the nominees for BEST EASY CROSSWORD.

Making easy crosswords is way tougher than it looks, and making easy crosswords that are still surprising and engaging is even harder. Despite that, this was a stacked category.

My vote went to Nate Cardin’s Untitled puzzle from the LA Times on February 25. Managing to find five phrases/compound words (OVERDRAFT, BODY WASH) where both parts could be followed by the word BOARD was an impressive feat of cruciverbalism.

WINNER: Jess Shulman for “Clear Up to Here?” (Lynn was the first presenter of the evening to do the “opening the envelope” gimmick for the winner.)

T Campbell and Laura Braunstein joined to present the next two categories.

Laura, one of the minds behind The Inkubator crossword, presented the EMERGING CONSTRUCTOR AWARD.

I sadly wasn’t familiar with all of the nominees in this category, so I had to go with someone whose puzzles I felt I’d had a good sampling of. My vote went to Carina da Rosa, whose work in Puzzmo and LilAVCX I’d enjoyed throughout the year.

And it turns out I wasn’t alone in my assessment!

WINNER: Carina da Rosa

T Campbell did a wonderful introduction about what separates BEST SUNDAY-SIZED CROSSWORD from the usual crossword fare before reading the nominees.

Despite the sheer ambition of “Just One Clue 2” and its crowd-sourced cluing, my vote came down to either the grid shape wordplay of Jonathan Raksin and Jeff Chen’s “Self-Starters” and the diabolic vocabulary in crosstina Aquafina and erik agard’s “themeless no. 36.”

I mean, we got SATAN WORSHIP and TWO CHEEKS OF THE SAME ASS, neither of which I’ve ever encountered in a grid. That being said, my deep affection for visual gimmicks in crosswords won out here.

WINNER: crosstina Aquafina and erik agard’s “themeless no. 36.”

Stella Zawistowski and Kim Vu were the next two guest presenters, with Stella handling BEST VARIETY CROSSWORD.

I love variety crosswords, because there are so many ways you can play with the traditional crossword formula to make something new and exciting. Rows Garden and Marching Bands puzzles are deviously designed masterpieces when constructed well, and this category showed off skill and cleverness in equal measure.

My vote went to a puzzle style I’d never seen before, as Ryan Faley’s “Nonplussed 4” combined across and down cluing with a non-traditional grid and a Rows Garden-style interior shape (pluses instead of blooms). I loved the construction and creativity, and the revealer was the cherry on top. Terrific stuff.

WINNER: joon pahk’s Two Outta Three Ain’t Bad

“joooooooooooooooooooooooooon” calls rang out both over the stream and in the chat to celebrate joon’s win.

Kim then read the nominees for BEST TOURNAMENT CROSSWORD.

Tournament puzzles are invariably bangers because they can push the difficulty AND creative envelopes, and this category was LOADED with heaps of cool ideas and challenges. (Last year’s Lollapuzzoola alone could have filled this entire category.)

The two puzzles that stuck with me the most were David Steinberg’s Westwords puzzle and Kareem Ayas’s Wild Discoveries puzzle from Lollapuzzoola. They were both wildly inventive, challenging, and above all else, memorable. This was the toughest choice of the entire ballot.

In the end, Kareem got my vote. And again, I wasn’t the only one impressed by his playful puzzling.

WINNER: Kareem Ayas for “Wild Discoveries”

A brief In Memoriam played next, offering tongue-in-cheek farewells to Deb Amlen (for ending her tenure with The New York Times), the Browser Crossword, and the free version of The New York Times Mini Crossword.

We then got a sincere send-off for influential creator and puzzle icon Mel Taub.

Our next two guest presenters were Peter Collins and Vic Fleming. They had a great little gimmick involving a swear jar and a virtual handover of $10 to celebrate the eventual winner of BEST CLUE (and my favorite of the nominated clues):

WINNER: [They might have “fuck you” money] for SWEAR JARS by Amie Walker and Amanda Rafkin, AVCX, April 18th

They next presented BEST THEMED CROSSWORD, which was another stacked category.

This category was a case of leading with your strongest contender, because Ada Nicolle blew me away with “Would You Let Me Finish” from Apple News+ on January 5th.

The grid is populated with longer entries that, when the last letters are removed, form the actual answers to the clues. So GOT THE ICK becomes GO-TH-IC, for example. It’s a great gimmick and a fun reveal when you get it.

WINNER: Untitled by Adam Wagner and Rebecca Goldstein

Rafael Musa, Ryan Fitzgerald, and Ben Gross then interrupted the proceedings for an interactive game with the audience. But first, they had a surprise award to hand out!

The Leviathan Award celebrates important contributions to the world of crosswords, so Ryan was blindsided by this award for creating the crossword software Ingrid. A video full of kind words from fellow constructors was played. It was heartwarming stuff.

Three instances of a puzzle game called Bracket City challenged the audience next. The goal was to unravel a series of crossword-style clues nested within each other, like so:

I doubt I was the first to solve this puzzle, but I was the first to post the solution in the chat: BLACK AND WHITE.

Work from the inside out with the brackets. [gun, as an engine] is REV, so you get [REVolving __] for DOOR, then [Friday with REVolving DOORbusters] for BLACK. [south of Spain] is SUR, so you get [flag raised in SURrender] for WHITE. BLACK AND WHITE is the final answer.

David and Ophira solved the first two puzzles live while the audience solved at home, and everyone was challenged to solve the third (and most complicated) bracket city puzzle in their free time. Can you unravel it?

David and Ophira continued the awards and presented the next category, BEST MIDI CROSSWORD.

As was the case with several categories, we were absolutely spoiled for choices when it came to midi crosswords. Crossword Gentleman Doug Peterson had a great one, we had ablaut reduplications from Alex Rossell Hayes, a tightly constructed foursome of BOOM-based entries from Amie Walker, and Peanuts grid art from franci dimitrovska.

But I had to go “By the Numbers” by Kaye Brown. The sheer ambition of a LOST-centric puzzle with character names reading across and aligning with the infamous numbers from the show. It’s a fantastic bit of constructing wizardry.

WINNER: Amie Walker for “Bangers”

Our next presenters were Brad Wilber and Mangesh Ghogre to handle the one-two punch of BEST CRYPTIC CROSSWORD and BEST VARIETY CRYPTIC CROSSWORD.

I have been on a quest to improve my cryptic crossword solving over the last few years, so the nominees in these two categories put me through my paces! The devious cluing was at its peak in the cryptics, and I think I spent more time on each cryptic than I did on any two or three of the puzzles in the other categories!

Amidst all the tough cluing and interesting vocabulary, it was Jamie Ding’s AVCX Cryptic and The Rackenfracker’s “High Definition” who got my votes this year.

WINNER, BEST CRYPTIC: PiGuyN for “pi guy cryptic 22”

WINNER, BEST VARIETY CRYPTIC: The Rackenfracker (JonMichael Rasmus & Sean Weitner) for “High Definition”

Our penultimate pair of guest presenters were Katie Grogg (looking glam!) and Jared Goudsmit. They presented the nominees and some great puns as well (and made a strong case for hosting next year’s awards).

The first award they presented was BEST CROSSWORD-RELATED MEDIA.

This is a new category for this year’s ORCAS, and as you can imagine, I was absolutely stoked to be included amidst a murderer’s row of excellent, insightful commentary on all things crosswords.

I quite selfishly voted for a PuzzCulture piece, as I was immensely proud of “The Curious Case of Richard Simon’s Aunt, Hedwig.” I didn’t expect to win, and was very content just for the opportunity for new eyes to find the blog.

WINNER: Adam Aaronson for “Square Theory”.

The chat was so chuffed for Adam, with several shouting out his post as eye-opening and game-changing. Congratulations Adam!

Katie and Jared then presented BEST CROSSWORD COMMENTARY.

I love the behind-the-curtain glimpses offered in columns like Rex Parker’s, Wordplay, and the LA Times Crossword Corner, many of whom have been commenting crosswords longer than some of the attendees have been making crosswords or solving them!

All of these nods are well-deserved — Deb and Malaika are brilliant, distinct voices in the crossworld — but it was “Malaika Handa and Stephen Lurie” by Renee Thomason that got my vote.

WINNER: Sally Hoelscher for “Terrors of the Deep”

Our final two awards were presented by Christina Iverson and the very dapper Andy Kravis. First up was BEST THEMELESS CROSSWORD.

This one was a three-horse race for me, with killer efforts by Paolo Pasco, guest host Christina, and Erik Agard, all chock-full of great vocabulary and ambitious crossings. I finally managed to narrow it to Erik’s August 18th New Yorker puzzle when it came to my vote, but really, any of these three would be worthy winners.

WINNER: Erik Agard’s August 18th New Yorker puzzle

Finally, it was time for CONSTRUCTOR OF THE YEAR.

I genuinely have no idea how you even narrow down nominations for this category, because there are SO MANY talented constructors. My shortlist would be 30 people deep, easy!

Each of the puzzles included in the Trevor Project Puzzle Pack represented the nominees well, but it was Rafael Musa and Adam Wagner’s puzzles that stuck with me the most. I loved the gimmick in Adam’s “Endless Loop,” but in the end, I went with Rafael Musa. Each time I saw that name in the byline, I knew I was guaranteed a terrific solve.

WINNER: Adam Wagner

Adam was there to accept and gave a very sweet speech, celebrating the welcoming crossword community and the support of his wife and family. Amazingly, he only started constructing in 2019!

You can’t complain about an award show that only takes up an hour of your time, especially when Oscar and Emmy broadcasts can last into the wee hours. And the crossword community is full of quirky, likable folks, so anytime you can get a bunch of them in a room (virtual or otherwise) together, you’re guaranteed a good time.

I thought it was a little weird that the games got more time than some of the categories, but this was my first ORCAS. Maybe that’s how the show usually goes!

Congratulations to all the winners! There were so many amazing puzzles published last year, and it was a pleasure to get to solve so many mind-bending, entertaining, and lovingly crafted cruciverbalist creations.

It was cool to see 5 out of my 15 selections get the nod (and a few other winners in my honorable mentions). And I’m already taking notes to contribute nominees to next year’s ORCAS!

What did you think of the ORCAS, fellow puzzler? Did your favorites win? Was there a puzzle you loved that you wish had gotten more of a spotlight?

Let me know in the comments section below. I’d love to hear from you!