Gary Con as a total noob — A level 0 attendee gets some XP and maybe levels up.

Until this year, I’d never been to a gaming convention. I’ve got a lot of friends who have. They’d come back from GenCon or PAX or wherever with tales of how much fun they had, the people they met, etc. Woven into all of these stories are snippets of the endless logistical issues those big conventions come with, something my brain likes latching on to and blowing out of proportion. Are they still worth it, despite all the little headaches? Probably, given how many people love going. For me though, I like to work up to things, to be at least somewhat prepared.

Then I heard a friend talking about Gary Con. He was saying what a great time he’d had in 2024. It didn’t sound too different from stories of other conventions he’s attended (and he’s been to many!), but I noticed it was scaled down, without all those bits with the huge crowds, long lines, and miles of walking between various event halls I always pick up on. I decided this was a con to check out, perhaps my springboard to bigger cons…or maybe what I was looking for all along.

A small Wisconsin town during the edge of spring is not the most obvious choice for a convention. Giving it a name like “Gary Con” doesn’t explain much either. For those that know, it all makes perfect sense. For those that don’t, it is a convention dedicated to celebrating the life and games of Gary Gygax, the legendary creator who gave us GenCon, D&D, and TSR, Inc. Gary Con got its start from gaming sessions that happened after Gary’s funeral in 2008. It was suggested to Gary’s son Luke Gygax that those sessions should be a yearly event, and here we are. Despite its year over year growth, having the convention remain in Lake Geneva, Gary’s hometown and the birthplace of TSR and of D&D, just feels right. And being there, huddling around a table, rolling dice and avoiding that midwestern March weather is as close to the roots of the hobby as it gets.

Few towns this size have a place to host an event like this. That Lake Geneva has the perfect facility for such a convention almost feels like fate. The Grand Geneva Resort is a sprawling, almost maze-like complex of connected buildings done in Frank Lloyd Wright’s prairie style. It has rooms in unexpected places and stairs that aren’t traditionally symmetrical. You can start on the ground floor heading to another section, go down multiple flights of stairs or ramps, and somehow still be on the ground floor. The result is a place that doesn’t feel too far off from something Gary himself might have sent players through, and based on the official map for the convention, they know it.

Still, the resort is not so large as to be confusing for long, and I felt I had a handle on things within a few hours. With the exhibition hall a good distance from the main convention rooms, and numerous side rooms dotted around different locations, the resort manages to never feel particularly crowded. Even the special events are able to fit nicely into their locations, and it’s a credit to the resort and the staff that they can accommodate the equivalent of half the town showing up at once, while making it seem routine. 

With the convention centered on Gary’s life and accomplishments, it’s no surprise that there is a heavy focus on the earlier eras of gaming that he helped popularize. In terms of special guests, it means quite a few of the people who knew Gary or were at least his contemporaries. The con is well attended by early luminaries whose settings I played in, books I read, and art I admired. Not to be left out is the new wave of creators and personalities from other platforms. The end result is a fantastic mix of folks giving presentations, sometimes together, with all kinds of interesting stories and insights about the games and the game industry. I would have been happy just filling my days with all the panels on offer, but that’s not the real reason to attend.

The real reason is the games, and in particular, RPGs. Dungeons and Dragons dominates, but there’s almost as many people playing older D&D as there are 5th Edition. Effectively every version of D&D made it to a table at some point, right down to the different flavors of Basic. Nipping at D&D’s heels was the pack of Old School Renaissance and retro-clone games. Entire rooms were set aside for Castles & Crusades and Shadowdark, and you didn’t have to pass many tables to spot one of Goodman’s “Crawl Classics” games.

It wasn’t all fantasy or old school. I saw RPGs from every genre and era of the hobby, there were far too many to list. And it wasn’t all RPGs either. Board games and especially wargames were quite common, including some sessions of Avalon Hill’s Outdoor Survival, the hex crawl board game that Gary directed D&D players to use when not in a dungeon. I don’t know wargames that well, but I loved walking through the dedicated wargaming ball room and checking out the setups. With piles of painted up armies and terrain far more elaborate than what I’ve seen at most local game stores, it became a visual representation of why gaming at cons is so popular: the opportunity to play things you wouldn’t normally play, or play your favorites in a different way.

This being my first outing, I was too timid and only signed up for a few games, spending most of my time seeing panels and talks. Roleplaying in front of friends isn’t always easy, and roleplaying in front of strangers is just about a half-step away from theater improv and all the anxiety that can provoke. Turns out, it’s not something to be that worried about. Once I got to the table, knowing this character and group was going to last about 4 hours at most, getting into character was quite liberating. I didn’t have to be concerned that something I did would mess up my character or the campaign long term. The only concern is making it a memorable time. The other players are doing the same thing, and the end result is often some wonderful chaos with some new friends.

So far, it probably sounds like a lot of things you’d find at other cons. That applies to other stuff as well, there’s game tournaments, autograph booths, a cosplay contest, and so on. However, there is one thing Gary Con has that no other con has, and it’s not just Hawaiian shirt day, it’s a living room. The hallways that branch off the lobby of the Grand Geneva are loaded with couches and chairs, and there is a large lounge right off the lobby. The upstairs is an open catwalk-like area with game tables and more seating that overlooks the lobby and lounge. Anyone passing from the major areas of the convention to other areas will come by the lounge section.

This “living room” is the heartbeat of the convention. With a bar in the lounge and a coffee shop and cafe in the immediate area, almost everyone ends up there several times a day. This is particularly true later in the evenings, when the official events are mostly over and people are wondering what to do next. The overall space can hold several hundred people without too much crowding, and everyone is packing fresh tales from their day of gaming. As something of a social butterfly, I was often in the lounge area late into the night.

So how would I, a con noob, know this is something unique to Gary Con? Well, I can’t know it personally, but it is something I was told repeatedly by numerous, more experienced con goers. In these conversations I heard stories of recent games, of past games, and of other cons. They cited this hangout spot as something of a unique highlight of Gary Con. We had serious discussions on various systems, books, artwork, where the hobby was heading, even stories of meeting Gary, all with people I’d met minutes before. These kinds of conversations were happening all over the lounge. Occasionally they’d lead to impromptu pick up games, and people would head over to a nearby empty table and start playing.

A frequent topic was Gary Con itself. So many of the people I spoke to were on their 2nd, 5th, 10th, even 15th visit, that at times I felt as though I might be the only first time attendee in the whole convention. While the stories of how these folks first came to the convention were fairly unique, most of them ended in roughly the same way: “I knew I had to come back.”

The lounge hangout was truly one of the great reasons to attend, just spending time with all these people who all have at least one thing in common: a love of games. The best descriptor I’ve come up with is that it was like being at a family reunion and discovering there was a cool cousin there who was into all the stuff you are. Except here, everyone was your cool cousin.

The convention flew by in a whirlwind, and it took me a bit of time afterward to process everything I’d experienced. On the subject of gaming conventions, I have a few conclusions. The first is that, as mentioned earlier, gaming at a table full of strangers isn’t nearly as much of a concern as I thought it was. If it’s a thing you feel anxious about, nothing I say is going to alleviate that better than trying it yourself, but it’s worth it to push through. 

Secondly, I have no doubts that attending a convention like this will make you a better player, and a better gamemaster. From a play perspective I managed to cram more new gaming into four days than I typically experience in a year. However, even just walking around and seeing what was happening at random tables was a source of great inspiration for both sides of the GM screen. Just having that level of contact with so many other people, you absorb new ideas almost like osmosis.

Now, specifically to Gary Con, I think it’s obvious I had an amazing time. I met a lot of great people and made some new friends I really hope to see next year (or sooner!). I’m not in a position to make many comparisons to other cons, at least not yet, but I suspect it’s going to be a tough one to beat. I don’t think I’m ready to leap into something like GenCon or PAX yet, but there’s something in between that will be a good fit. And while I’m doing that, I’m watching the Gary Con countdown ticking down so I can pounce on next year’s tickets. Like the people I met, I have to come back.

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