I think there are two angles we could take here. One would be something "Boston." For example, one idea is the red sox "two socks" logo but instead of the socks, cowboy boots. (see logo here:
http://logoshak.com/~asgsport/images3/RedSox3.gif). There are other Boston images as well.
Another angle is the Beacon Hill part of the Beacon Hillbilly. Beacon Hill is a very expensive, upscale, preppy neighborhood. Imagine Burberry and pearls on the girls...sweaters over the shoulders..you get the idea. Perhaps there is something amusing wherein redneck meets upscale. Preppy-redneck. Down-home rich. Redneck with Money
Side comment: the bar doesn't exist (yet). I'm looking into it now, and think it would be fun to build interest by first building the brand and support for the idea.