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Yes, it’s a terrible name for a convention.

The organizers will be the first to admit it. The name comes from the organizers’ name for their game space. That game space, much like the convention, is a hidden gem. It’s full of museum quality copies of D&D products throughout the nearly 50 years of the game’s existence. It’s also full of the things you might expect in a modern purpose built game space like a dedicated gaming table and a sound system. It sums up GameHole Con perfectly; mindful of the past with an eye to the future.

Growing up in Milwaukee, I never truly appreciated Gen Con until it left in 2003. I was able to roll out of bed, meet up with friends, and go to a massive convention at the heart of an industry without worrying about hotel rooms, travel arrangements or finding good places to eat. Yet I knew that the city never really embraced the show like Indianapolis. It pains me to be the one to tell folks that Gen Con is never coming back to Milwaukee. There have been other shows that have tried to fill the void but none of them have been successful. And here comes this show in Madison, a scant hour to the west, that does just that.

If anything GameHole Con started out resembling the one recent convention that’s flourished in the past few years in Wisconsin; Gary Con. There are still plenty of TSR Employees and die hard fans kicking around the cradle of RPGs. The nostalgic build of Fifth Edition brought the Wizards team back to Wisconsin in the spring with a second trip in the fall for Gamehole Con. It’s a small convention, but it’s one where you can see team members like Jeremy Crawford or Chris Perkins in the hallway and say hello.

The show has grown to include other companies as well, such as Monte Cook Games, Onyx Path, Chaosium, Beadle & Grimms and more. These are big players in the industry in a dealer room that still has space for small dice manufacturers and indie game developers. There isn;t the busy buzz of a Gen Con or an Origins, but it’s still easy to catch a seminar with influential people or even play a game run by one of them.

Streaming has also become an important part of the show. Without my experiences drinking on camera to raise money for sick kids, I would have never gotten the bug to start Theatre of the Mind Players. There’s a fantastic feeling of knowing that putting out RPG silliness helps people and I enjoy jumping into as many charity streams as I can at the show.

The key is the execution. Small shows tend to be chaotic affairs but as both an attendee and a guest GameHole Con puts other shows to shame. No sweating about tickets, clear communication of policies and an adorable John Kovalic monster every year. A perfect example of this happened this year. Madison has an indoor mask mandate this year due to COVID-19 and while other shows waivered in enforcement, GameHole Con stood firm. There was some drama on their social media because of it, but I felt safe at the show in a way I haven’t felt in nearly two years of going out in public.

GameHole Con returns to Madison October 20-23, 2022. If you are in the area at that time and want a big con feel with much less big con hassle, I hope you’ll join me next year.

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