Chocolate Festival of Texas
The answer is about five half-glasses with no obligation to pour any out, and enough chocolate to make you consider trashing all remaining Halloween candy. There were chocolates and there were wines, but the most notable finds fell into the "both" category.
A chocolate wine: Landon Winery from McKinney boasts a limited-production "Chocolate Finale" red dessert wine, which has to be one of the more tolerable dessert wines I've had--it's not syrupy and overdone but chocolately in a dark way that blends flavors well.
Wine chocolates: Quintessential Chocolates from Fredericksburg specializes in liquid-filled chocolates with a twist. Unknowingly I tried the Kentucky Bourbon flavor. When I made a face, the owner mentioned something about failing to check IDs, then explained to me that they use real wines and liquors in their treats, not just a sugary sweet cherry-cordial-like center. While the candy-coated straight shot of bourbon at 10 a.m. caught me by surprise, the Chardonnay flavor was delightful and might be stuffing a stocking or two next month.