My own personal dilemma with the whole thing is that dry red wine (what you'll find in the Yakima Valley, for example) and chocolate don't really go together.
I know. Blasphemy, right? In all honesty, I think people like the idea of red wine and chocolate going together better than the actual result. Both are romantic. Both share many similarities agriculturally and chemically. However, your piece of dark/milk chocolate is more often than not going to be at odds with your dry Cabernet Sauvignon. Or Merlot. Or Syrah. Or Lemberger. Or Sangiovese. Or Pinot Noir.
Rather than make this point myself, I will direct you towards some third party sommelier takes on the issue:
"Wine and chocolate can go together, but you need to match sweetness with sweetness, so avoid trying to pair a dry red wine (like Cabernet Sauvignon or Pinot Noir) with chocolate, and instead look to some great dessert wines like Vintage Port and Madeira from Portugal, or sweeter versions of sherry from Spain." - Thomas Pastuszak, NoMad
"Wine and chocolate can be challenging. Chocolate is sweet yet tannic, can be overpowering and can ruin a good wine. But chocolate doesn't have to be just for dessert! What about including the chocolate in the main dish?" Savanna Ray, Wildwood
"Pairing wine and chocolate is difficult. One that works: Banyuls (a sweet, fortified red made from mostly Grenache in Southern France)." - Jill Simorski, Hotel Jerome
"Despite the affinity for one another, many wine and chocolate pairings fight for the same ‘palate space’ making the whole experience taste like crap." - Madeline Puckette, winefolly.com
The consensus seems to be that sweeter, often fortified wines are a proper match to chocolate, and I have to agree.
So what's a winery to do? We like the event, we like the Yakima Valley Wine Association, we like that our visitors have a great time, so we participate. But we participate by taking Savanna Ray's advice and incorporating chocolate into a savory offering rather than a dessert. We don't make a sweet/fortified red wine, so that's not a really good solution as far as this event is concerned.
For that reason, last year we had a savory offering with chocolate being a very tiny ingredient overall.
This year Molly is putting together putting together a Oaxacan mole dish that will again fall on the savory side of the chocolate spectrum. In fact, chocolate constitutes such a small amount of the overall dish it might be a stretch for the event. But I digress. We will be breaking the mold for the event, and I hope that after tasting dessert-oriented offerings all weekend, our guests will enjoy a more substantial savory offering to fill up a little bit for a long day of wine tasting. That being said, I still anticipate Dry Riesling or Rosé being the best pairing with the dish. We'll see how it goes when all of the cooking is finished on Friday evening.
Thank you to Serious Eats and Wine Folly for quotes used in this article.