Inside Rolliefest, the Superbowl of Watch Collecting Meetups

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On a sunny Friday morning in late September, about 200 collectors, dealers and watch world hangers-on rode the elevators up—way up—to Aspire, the private events space on the 102^nd floor of One World Trade Center in Lower Manhattan, for a four-hour brunch where food—the menu included a spinach and mushroom quiche followed by plates of chicken and waffles—was utterly beside the point. (So, for that matter, was the nearly-360-degree view, which stretched from the Brooklyn Bridge, past Lady Liberty, across New Jersey and back around to upper Manhattan.)

That’s because all eyes were on the watches—some $20 million in timepieces displayed around the room, but chiefly at a long central table where piles of Rolex Mil-Subs, diamond-set Patek Philippe Nautiluses, and yellow gold Cartiers mingled with far rarer and more esoteric wristwatches in a horological orgy of truly jaw-dropping proportions.

“All the events I’ve been to, I have never seen this many watches on a table at once,” the collector Jason Gong, founder of Complecto, told Robb Report. “Never mind the value. And then the owners just kind of get up and walk away and wander. It speaks to the level of trust in the room. Everyone has such reverence for the watches, and they really do handle them with such care.”

Welcome to Rolliefest, the super-secret, invite-only, biennial watch event that celebrated its third edition last week with a series of gatherings that have been described as the watch world’s equivalent to the Super Bowl. Founded in 2019 by Geoff Hess, a vintage watch collector and auction house veteran who now serves as global head of watches at Sotheby’s in New York, the fest, which this year cost $1,500 per attendee, has grown in fame and size since its first edition.

“We started with 110 people in 2019,” Hess said. “The next Rolliefest, in 2023, was 175 people. This time was 210. And based on the number of messages I have, it could have been 410, which I don’t necessarily want. But I’ve really enjoyed watching people gravitate to it. And the essence of it, again, is that it shows that watches tell time, but what they really do is connect people.

“It’s why people are not judged by the value of their collection here,” he added. “They’re judged by their character and the stories that the watches tell. There are big watch events all over the world—Watches and Wonders, what have you—but there aren’t a large number of meaningful watch events that are for the collector. There’s no brand behind this. This is really just collectors coming together to share their passion.”

The festivities kicked off Thursday night with a gala dinner at the Metropolitan Museum of Art’s Temple of Dendur gallery, where the ancient Nubian temple, a gift to the United States from Egypt, has been housed since President Lyndon B. Johnson awarded it to the museum in 1967. Diners enjoyed autumn chicory salad and seared filet mignon in the soft glow of the lights illuminating the temple’s Aeolian sandstone walls and snapped wrist shots against the backdrop of the reflecting pool, meant to evoke the West Bank of the Nile.

For the Rolliefest finale, Hess and his team of organizers arranged a farewell cocktail party in the winter garden of the new private residences at the Waldorf Astoria, fresh off an almost-eight-year, multibillion dollar restoration.

The heart and soul of the event, however, was the watch sharing luncheon, where “absolutely all brands” were welcome, as specified in the invitation. Collector Phil Toledano, co-founder of the boutique watch brand Toledano & Chan, was impressed by the mania he saw among Rolliefesters. “Basically, what happens when you get this many watch people together is it’s like everyone is five years old and they’re opening their presents at Christmas,” he said. “And it’s just a frenzy to see stuff, to handle it. It’s unalloyed enthusiasm and joy.”

At one point during the brunch, Gary Shteyngart, the author and watch collector, wandered over to a table where collector Grady Seale, who’d flown in for the event from the San Francisco Bay Area, was showing six timepieces, including a skeletonized Kari Voutilainen model, a round, ultra-slim gold Cartier from the 1970s, a Patek Philippe Ellipse pocket watch, and a Type 4A model by the Japanese watchmaker Naoya Hida. Shteyngart immediately gravitated to the Hida.

“I love vintage, but this to me is like an elevation of vintage for contemporary times,” he told Seale.

His comment underscored the wide variety of timepieces, and timepiece lovers, at Rolliefest. While many were vintage collectors drawn to pieces boasting extraordinary provenance, there were also plenty of indie fans toting watches by the likes of De Bethune, F.P. Journe and Roger Smith. It was the sheer volume and breadth of wristwatches—as well as the undeniable glamour of the venues—that struck first-time attendee James Lamdin, founder of Analog:Shift.

“It’s more grand than I expected it to be,” he said. “$1,500 a ticket—it’s easy to balk at that, but when you think about the meals, the locations, the swag, the access. Listen, all of this stuff costs money, but you don’t need to spend money to enjoy watches. You don’t need to spend money to interact with other people in the watch industry.”

While that is certainly true, there’s no denying that Rolliefest represents the ne plus ultra of watch meetups. And this year, even collectors nostalgic for the early days of the hobby, before social media and investment watches entered the picture, said the vibe felt just right.

“I have this sense of community that I haven’t felt since the early 2000s,” the collector and dealer Kevin O’ Dell said. “Things felt more magical in the early 2000s from a community aspect. But I’m feeling that feeling again. There was something different about Geneva Watch Days this year—the sense that there were a lot of people there that were genuine, that were there for the right reasons—and Rolliefest was a continuation of that feeling.”

The only question that remains: How will Hess top himself for the 2027 edition?

“I won’t bet against Geoff,” O’Dell said. “I don’t know how he’s going to do it, but I know he will.”

To hear what other Rolliefest attendees had to say about this year’s event and the most memorable watches they saw there, check out our roundup of quotes below:

James Lamdin, founder & vice president of vintage & pre-owned, Analog:Shift

What was the most memorable thing you saw? “Seeing the absolute scrum of affection for the pile of watches laid out at lunch at the World Trade Center. The setting, the sheer volume of interesting watches that went far beyond just Rolex or the usual suspects. It was very impressive. And nobody wanted to sit and eat. Everybody just wanted to crowd the table.”

Mike Nouveau, vintage dealer, unofficial king of WatchTok

What was the most memorable thing you saw? “Andrea Parmigiani’s cloisonne enamel Rolex. There are only 10 of them in the world. It’s an extremely rare Rolex from the early ‘50s. It’s maybe a million-dollar watch. I saw like five different Mil-Subs, which were cool. God, I saw so much stuff. It’s hard to even remember. You get desensitized. I go to an event, I hope there’s like one watch I can shoot. This was like, ‘Oh, just the Paul Newman Daytona?’ Yeah, sorry. That’s not going to cut it.”

Did you sell stuff here? “I actually did sell—a ladies Datejust with a blue Stella dial that I sold to a dealer today. Right off the table.”

What are you wearing? “I’m wearing a 1948 Patek 96 with Arabic numerals on a gold bracelet. The watch was probably sold by Tiffany. And it’s a made-in-New York Tiffany bracelet.”

Erika Ratini, aka @WatchMissGMT

What was your take on the event? “I’ve really never been to another watch event of its caliber. I could talk all day about how amazing the Temple of Dendur or the observation deck at One World Trade were, but what really made this event so special was the amazing people who attended. Everyone there was so warm, welcoming and eager to share their passion for watches. I got to see so many rare and unique watches that I’ve never had the opportunity to get so close with to learn about.”

What’s the most memorable thing you saw or heard? “What will really stick with me was standing on the 102nd floor observatory of One World Trade, staring at a 30-foot-long table filled front to back with some of the most unique vintage watches I’ve ever gotten to handle.”

Fred Savage, founder, Timepiece Grading Specialists

What was the most memorable thing you saw? “Mike Nouveau had a Futurematic by Jaeger-LeCoultre, which has been one of the watches I’ve coveted for a long time. I’ve only seen one or two in person before. There was a table full of spectacular watches, but personally, I liked that Futurematic. It’s a round watch. And it’s got a day/night indicator and a power reserve indicator and these two small little circles on the dial. It’s really distinct looking.”

Why was it important for you to be here? “Not to get too poetic about it, but honestly, the people, the community. It’s literally a room of my favorite people. And people that I not just know through watches, but who have deeply enriched my life in really important ways.”

Grady Seale, collector from the San Francisco Bay Area

Why was it important for you to be here? “I really enjoy connecting with people who have a deep passion for watches. And this event tends to bring together a bunch of people who know an incredible amount about watches and the history, the craft, all sorts of things. It’s funny because it’s named Rolliefest, but it’s very much not Rolex specific.”

Kevin O’Dell, collector and dealer from the Washington, D.C. area

This was your third Rolliefest—what was your takeaway? “In my view, there was a big jump from the first Rolliefest to the one in ’23. The one in ’23 was epic. I felt guilt being there without my wife. The first one felt really nerdy, but the second one was fancy and fun.

“From 2019 to 2023, Geoff really took it up a notch. I thought, ‘Man, you’re really setting the bar so high. There’s no way he’s going to do better than 2023.’ But then I was surprised he really did outdo himself. The Met, the candles, One World Trade. It was just epic.”

What was the coolest thing you saw? “As far as watches go, one watch I saw was for sure my favorite watch of the whole thing. I was aware of it but hadn’t seen it in person. A friend of mine, Mitch from Connecticut, he bought a Cartier Tank Louis London from the ’70s. (I’ve been collecting Cartier since 2016.) This one is not really about the model but the fact that this example is so honest. All original, never been polished. It has a really cool personalized engraving on the back. It’s in such honest condition—it even has the original strap. That watch was made before I was born. I put it on my wrist, and I wanted to buy it but of course it’s not for sale. Mitch texted me that my Tank Normale was his favorite watch of the show and I said the same thing about his Tank Louis.”

Jason Gong, founder, Complecto

It’s your first Rolliefest—what’s your chief impression? “Being in New York, as big as a city as it is, if you’re in the watch world, it tends to feel really small. So you’re used to seeing a lot of the same people. But this is really one of the first events that I’ve been to where I didn’t know most of the people in the room. So just having the opportunity to meet and connect with folks from all over the world has been a treat.”

What’s the coolest thing you saw here? “I saw a lot of cool things. Where do I even start? I saw a Vianney Halter that was in a style that I’ve never seen before. Skeletonized resonance movement. It had a sapphire window on the side of the case so you can see the resonance in motion. That was one of a number of really outstanding pieces. Things that I never expected.”

What are you wearing? “A De Bethune DV27. It’s the version two. With the salmon dial. So it’s a relatively rare bird. I think I’m the only person here wearing a De Bethune. I didn’t even see any on the table, which was kind of interesting. I thought I might have seen like a couple here and there, but there’s definitely an aesthetic among the crowd. Last night, I saw more Langes and Journes than I did Rolex. Which is funny. But that’s in keeping with what Geoff is very explicit about: All watches are welcome. Just really funky tool watches and brands I’d never even heard of before. References I didn’t know existed. And I’m sure not all of them are million-dollar watches. But it reflects the breadth of people’s tastes and journeys as collectors.”

John Reardon, founder, Collectability

What’s the best story you’ve heard here? “A great story belongs to Grady Seale. It’s about his seven-year-old daughter finding a Patek Ellipse in a park and being able to return it to the original owner’s family after an eight-year hunt. It’s one of the most beautiful Patek Philippe stories I’ve ever heard.”

Paul E., collector from Colorado

What are you wearing? “This was a watch that was gifted to a family in Italy, a famous composer’s family. His name was Giuseppe Verdi. It was in the family from around 1939 until the present. And it was brought to market by another member of the family. The individual who got it contacted me. They knew my tastes. So I ended up buying it very early this past year. It’s one of only seven in the world known in steel. And the thing that makes it unique is it’s also unrestored. The other six have had some level of restoration done. And it’s hard to see with my eyes, but it says ‘Eberhard Milan’ on the dial, which was a retailer at the time in Italy. The backside of it is interesting, too, because it’s got an inscription from the royal family. The belief is that it was gifted by King Umberto, one of the last kings of Italy, to that family, and stayed in the family’s possession for that whole time. So it’s got the combination of rarity, condition from the standpoint of never being restored, and the provenance that, to me, makes it really a very interesting watch.”

Phil Toledano, co-founder, Toledano & Chan

What are your impressions of the event? “It’s my second Rolliefest. The first one was karma. This one is way more unhinged. I wasn’t even thinking about buying things. I mean, there are things that are super interesting to me. But I also have super weird taste. It’s very rare that I see something and think, ‘Oh, I have to have that.’ I almost have to find it on my own.”

What are you wearing? “I’m wearing an early 1960s Rolex 6234. I never thought I’d own this watch. I bought it last year at auction. It was always a dream, and I never thought it would happen.”

Ted Friedland, collector from Omaha, Neb.

What are you wearing? “This is a Roger Smith piece that I waited seven years to acquire. I met Roger at the 10th anniversary of Hodinkee, in 2018. I asked him how a guy from Omaha, Nebraska, could acquire one of his watches. He told me to email his wife. So I emailed Caroline, and I was grateful to be put on their list. I would check in periodically a couple of times a year to let them know that I was still breathing and interested, waiting to find out when I would be put on their production list. And then, lo and behold, I got the notification that I was getting ready to be put into production and got to do a Zoom call with Roger in early 2023. And I picked it up in mid-2024. It’s white gold Series One, time only. I wanted to remain true to Roger’s aesthetic, but I wanted to have my own little take on it, so I had him do the Roman numerals at 3, 9 and 12.

“He is a true gentleman. I went out for the inaugural British Watchmakers Day. And I knew that my watch was nearing completion. And Roger was one of the founders of the British Watchmakers Day. (I was actually there earlier this year for year two.) But when I went last year, I said, ‘I know my watch is nearing completion. I’d love to meet Caroline, and I’d love to see your workshop.’ And so I flew out to the Isle of Man for the day, and he picked me up, and we had lunch, and then he took me back to his workshop and his home adjacent to it. And I got to meet his wife, and I got to see where George Daniels worked. It’s just like a time capsule. He’s got all of his equipment and all of his documentation and paperwork, and it was pretty spectacular.”

How would you describe your collecting philosophy? “From A. Lange & Söhne to Zenith and everything in between. I started collecting probably 22, 23 years ago. I’m born and raised in Omaha. My father was a collector of many things. He was friends with the owners of [local retailer] Borsheims. It’s now owned by Berkshire Hathaway and Warren Buffett, but the Friedman family that owned it were a friend of my family’s. And when I was a child, I have memories of going down to their store on 16th Street with my father and him sitting down with Ike, the owner, and looking at watches, and being with my father when he acquired pieces.

“When I turned 13, for my Bar Mitzvah, he got me my first chronograph, this quartz Bertolucci that I still have. At the end of their production, they were pretty horrific-looking watches. But it was my first real watch. When I turned 16, I got this IWC chronograph and caught the bug.”