Berlin has a wooden kiosk in one of their parks with picnic tables around it. Each month a different German winery sells their wines by the glass or the bottle at promotional prices (maybe $2-3 for a glass and $8-12 for a bottle depending on quality). Residents enjoy sitting in the park and visiting with their friends while having some wine; they are also free to bring their own picnic foods to make it a meal. It's a way for people to enjoy the outdoors while also becoming familiar with the wines from the area. I think the idea would be great for San Antonio and for our Hill Country wineries.
I am not sure if Berlin hires a permanent staff for the kiosk or if the wineries staff it during their month; the former would probably work most efficiently. The wineries deliver the cases as needed throughout the month. A question to be resolved is the permitting process and who would apply for selling wine, but the project should be doable and could possibly work in two parks--the new HemisFair Park to introduce tourists and conventioneers to our wines and a Park like Hardberger for local residents.