Went to my first pony con today: http://www.sillyfillycon.org/
There was around maybe 70-90 people there. There were drawing, speed fanfiction, and cosplay contests (there were some awesome ones including Beatnik Rarity, and the shed.mov versions of Fluttershy and Dash XD), a few vendors, PMV expo (incl. an Iron Maiden one I made), and for guests there was Jessi Nowacking (Vinyl Scratch voice in videos including Epic Wub Time), DJ Shamrock of Celestia Radio (who was doing a live broadcast), and WhiteDove who (though she didn't have any for sale) brought along a dozen of her plushie customs that were consigned or from her own collection (the best was an absolutely awesome Luna one).
I picked up 4 buttons and a patch there, plus I won a blind bag for my entry into the art contest. Also picked up the Trixie brushable at the Target near where the con was held. I brought a few of my customs along including my Octavia blind bag, which caught Jessi's eye.
Oh and it wasn't 100% older men and women there. A mom and her 6-8 year old daughter showed up.