Going to surprise my husband with a trip to gen con. Looking at booking his flight from Thursday, leaving Saturday late morning. Worried that Saturday is the best day, and maybe I am cutting his trip too short? Saturday August, 19th is his birthday, so I wanted to book his ticket home for a surprise birthday party when he gets back.
 
 
Here are some of my questions:
 
What days are the best to attend?
Are there any events that I need to preregister for?
Any other off site or after show things he should check out?
 
TIA

Saturday is the most crowded day, but they are all pretty good.  

One event that you may want to preregister for would be True Dungeon.  The tickets do sell out and it is a pretty unique experience.

If you have him arrive Thursday and leave Saturday, that only gives him Friday to enjoy it. Friday is great, but I think at the very least a Friday and Saturday stay would be the minimum I would think would be enjoyable. Otherwise you are traveling all the time.

If he needs to be back on Sunday for some reason, then get him a late night flight.  Saturday is the heart of GenCon.  You can rest at home.  :-)  And you'll save money on air fare.

You have not said what your husband enjoys.  With that information the folks here can offer a lot more specific advise.

And I second the True Dungeon experience.  It is mind blowing that the die-hard players of TD do and how much they spend on it!

Also, are you coming too?

My husband enjoys D&D, and example of games he plays are but not limited to: Bloodrage, LOTR, Catan, etc. Right now he is painting the miniatures of Zombicide: Black Plague. Sometimes he watches the show Acquisitions Inc. and board game reviews on you tube. 

Beyond board games he is into Historical European Martial Arts, swords, etc. 

I will not be attending, but he will be going with his brother. They are both from Italy. 

Any additional recommendations, knowing a little more? 

Make sure you have a hotel room booked.

You can see the old list of events from last year here:

http://gencon.eventdb.us/

I would recommend  getting him a pass to the board game library (under Isle of Misfit Events), true dungeon, some AD&D tickets or board game event tickets.

You could also get him some generic tickets. That way he can go join areas that interest him and his brother.

I know this might sound judgmental but just sending him thursday, a whole day friday and shipping him back saturday MORNING is a Bad Idea. You're spending all the money, why not let him enjoy it? He'll already be missing most of thursday by traveling in then.
I realize YOU want his birthday party saturday night but trust me. The gencon surprise will backfire if he then has to leave again right away. It's like giving a two year old a piece of cake, letting him eat two bites and then TAKING IT AWAY.

For the next year all it'll be is 'Well, I heard about this really cool event but IT WAS ON SATURDAY so I had to leave.' He probably won't react as badly as the two year old directly to you, but...it'll be bottled up inside.

Really make it super special, he gets friday and saturday all day, flies back sunday, and you surprise him the week AFTER with that party, when he really really won't be expecting it.

Can you at least get him there Weds night?  BTW, plan on him wanting to come back next year.  And thh next. And the year after that.... :)