After discovering the very thriving tabletop gaming community in Chicago I looked around and discovered that there are at least a few good medium size gaming conventions in the midwest that I had not previously heard of (aside from Origins and GenCon, which are rather large). The top one on my radar was Geekway to the West, where maybe 2500 gamers congregate in St Louis each spring. A number of folks from irc://freenode/#boardgames recommended it, and I read good things about it, so I decided it was worth a couple of days off work to check out.
I took Amtrak from Chicago to St Louis, which worked out pretty well. It's about a 5.5 hour ride for $34 each way, which compares pretty favorably to $100 for a plane ticket for a much less comfortable 90 minute flight plus an arbitrary number of hours of airport hoop-jumping. I'm actually on the train home as I write this.
The first major hiccup came after I reached St Louis and took their Metro train and bus out to the convention hotel on Thursday afternoon. I had made plans elsewhere in the city for Thursday night and my last decade of big city living left me making the spoiled assumption that I would be able to arrange transportation in the few hours before those other plans. That was a mistake. At the convention hotel I found myself with no reasonable way to attend a late night event ~25 miles away. The closest zipcar and relayrides were 5-10 miles away, with light to no taxi infrastructure to get me to them. Calling a taxi to take me into the city would cost $50+ each way. All of the non-airport car rental offices within reasonable distance of the hotel closed at such ridiculous times as 5-6PM on a week day. Their airport counterparts remained open, but had nothing for less than $100 per day. In hindsight, I should have rented a car downtown, rather than taking the train and bus to the hotel. If I visit St Louis again, I'll keep that in mind.
Having my Thursday night plans ruined, I ended up working a volunteer shift and then being a hermit for the night. I decided that I'd rather start fresh on Friday morning. That turned out to be a great idea, despite the loss of some hours of evening/night gaming.
Between Friday, Saturday, and Sunday, I probably spent about 40 hours gaming, which I call a successful gaming weekend regardless of what else went on.
Regarding the gaming, Geekway has an amazing game library, where I spent my volunteer time. I donated a couple of games, the convention owns a few hundred, and a couple of board members also loan their own few hundred each as well. It was the best stocked game library I've seen at a con, and I'm including Origins' tabletop room and board room in that. Some resident techies have developed a library system to make checking games out and in as easy as barcode scanning the game and the person's badge, which allowed us to operate at a staggering pace, sometimes handling a dozen games in/out in a minute. This library, combined with many gamers' personal piles, kept a couple of 500-1000 seat rooms near capacity for most of the day, with just a few dead hours in the morning each day.
Separately, there is also another game collection entitled "Play and Win", filled with games donated by publishers and vendors and designers. Players record each time they play a game, and are entered in a drawing to win a copy of the game at the end of the event. That arrangement led to a lot more focus on repeat plays for some great games, which was a neat alternative to events where tournaments provide the only consistent recurring play opportunities. I played about a dozen such games, and ended up winning copies of two of them (Heroes Wanted and Scoville).
The event officially facilitates a number of ways for gamers to trade/buy/sell the games they want to get or get rid of. This year their "trade table" had about 500 games on it, with each person getting to choose whatever game they wanted after their own game was chosen by someone else. 60% of the entries did not get traded due to time constraints, but it was a neat event overall. They hosted a flea market for gamers to trade and sell with each other, which I did not get to attend due to a schedule conflict (read: I slept through it). Also, hosted by myself, they had a math trade arranged ahead of time for the first time this year. 41 of our 47 participants had at least one trade and 168 of the 477 games listed were traded. It was one of the most successful math trades I've participated in, by most metrics. If I attend again, I'll definitely run another one.
On the mediocre side, I found Geekway attendees a lot less likely to use "Players Wanted" signs at their tables. There may have been the normal number of people willing to play with strangers, as I encountered many groups who were willing or even wanted to, but many of them didn't know about the signs or didn't have them handy to use. As someone attending alone and relying on finding strangers to game with, this was annoying, especially during events (like the trade table and the closing ceremonies prize drawings) where I was forced to stay in one room for hours at a time, when I'd have been able to find a game to play much more easily in another room.
Aside from my transportation problem, nothing really bad happened. The worst things were just 'meh'. If I wasn't likely to move a thousand miles further away between now and next spring I'd say that I was relatively certain to attend again. As things stand, that's up in the air.