The last Trappist Beer Dinner we had before I sold Abbey had 65 people, each of whom paid $65 for it. Times had most definitely changed. 
I like to think that there are 2 kinds of Trappist Beer events - the on that has Westvleteren and the one that doesn't. I've done both. Personally, I say take whatever chances you have to, get the beer, charge the extra bucks, and make it happen. Cops? What cops?If ya don't know about Westvleteren, here is a small crash course.
From Wikipedia:
The Westvleteren Brewery (Brouwerij Westvleteren) is a Belgian Brewery founded in 1838 inside the Trappist Abbey of Saint Sixtus of Westvleteren in the Belgian municipality of Vleteren, not far from the hops-producing town of Poperinge and the medieval city of Ypres. The brewery and its beers are usually referred to as Westvleteren. The brewery's three beers have acquired an international reputation for taste and quality, as well as the limited availability of the beers which are not brewed to normal commercial demands.
Buyers were originally limited to ten 24-bottle crates of the beer per car, but as the beer increased in popularity, this was first reduced to five, then to three and now to two or one crates. For the Westvleteren 12 in 2009, it was limited to one case. When making an order now, the type and quantity of beer available for sale are revealed. Sales are limited to one order every 60 days per person per license plate and phone number. Also, the beer must be reserved on their "beerphone" beforehand. The monks do not sell beer to individuals who drive up to the abbey hoping to purchase beer. The reason for this is to eliminate commercial reselling, and hence give all visitors a chance to purchase the product.
The current production is 4750 hl (60,000 cases) per year, and has remained the same since 1946.
Aside from the brewery itself, the only other official sale point for the beer is the abbey-owned Indevedre, a cafe and visitor's center opposite the abbey. All beers can be bought there for immediate consumption or take-away, depending on availability (however, prices are higher than at the abbey). Often there is no beer available at the shop. The shop also sells cheeses made at the abbey, yeast tabs (not yeast to make beer but dead yeast for health) and other Trappist products.
Naturally, there is a tremendous amount of demand for Westvleteren's beers and they usually ranked among the best beers in the world. This being the case, there is a marked difference between a Trappist event with and a Trappist event without this legendary brew. 
So when Scott at Windy City asked me if we wanted to take part in a Trappist Beer Dinner, I was all over the idea. And he wanted the Westvleteren. YES! 
The Renegades for with the Trappist Brewery Chimay and I was to be there representing them. In addition to the blue cap bottles we'd be serving, I brought a gift of a 6 year old bottle of Chimay Grand Reserve for a "new versus vintage" comparison. Also joining us would be Mr. Rob Nelson of Merchant du Vin. Rob represents Orval, Westmalle, and Rochefort and the man knows hella lot about Trappist Beer. 
We stationed upstairs at Windy City in an area that is perfect for this type of gathering. The upstairs of the restaurant has a circular opening that looks down onto the first floor, which makes for an awesome atmosphere to have an intimate experience while still getting some ambient noise from the crowd below. A locale that I would dig watching some NFL Football and my beloved Steelers in, and am going to beg Scott to allow us to do so this season. 
The food that was offered for pairing looked amazing. As a non-meat eater, I am pretty well screwed when it comes to this type of event. When the smoked ribs to pair with the Westmalle Dubbel was coming out of the kitchen, I happened to be standing behind the server when she walked by with them. Oooh man, the aroma made me want to chew my own fingers off. 
We began with the Chimay paired with a salad and had the 2006 Chimay right after to observe the changes that 6 years have caused. A great way to show off what vintaging can do. Second was the Orval with a soup followed by the La Trappe Quadruple with the ribs. Next was a tenderloin with Westmalle Dubbel and the last pairing was a dessert with the Rochefort 8. The Westvleteren 8 was going to fly alone and needless to say was a hit. 
Above anything else, when you get to talkin' with someone in the business about Trappist Ales not only do you invariably find a lover of them; but you'll also get into a conversation about how they have influenced not only Belgian brewers but American brewers as well. It's awesome that you can easily point directly to a small handful of breweries who have had an incalculable effect on the entire industry. Outside of perhaps a few German breweries can I think of any group that have had that type of influence. I have attached a few resources if you want to further your education in Trappist beers, or perhaps run by your local bar that specializes in Belgian beers and get some hands-on schooling. Cheers!
