In my 5 years (or so) on Timmy Tour i\'ve never seen a South NOrwalk date. I am obviously bias at this point living right on Washington St. in the middle of SoNo, but it seems like it would make sense.
I wouldn\'t exactly call it a "heady scene," but there is plenty of traffic going through there Wednesday through Saturday and plenty of bars/clubs to play. Just off the top of my head...O\'Neils, Barcelona, Black Bear, Martini Lounge, The Loft, and Archie Moore\'s all have a stage and live music every week. Gingerman could also probably work as well with the right set up. Plus if he starts to do well there are plenty of opportunities to try out new bars (or even start a bidding war for his services)!
I think I talked to Timmy about this before and he seemed a little put off with the South Norwalk scene (i guess he used to live down here?). It just seems to me with BAR no longer the Wednesday night spot, it might be a good idea to give southern CT a try. South Norwalk (and Stamford for that matter) might be a good fit. The market is anything but oversaturated and might embrace a Timmy Tour show or two. Slightly older crowd (late 20\'s /early 30\'s) so there should also be decent money to be made in tips as well.
Big Markets in Southern half of CT are New Haven, Fairfield/BPT, South Norwalk, Stamford, and Greenwich. I know ffld hasn\'t exactly worked out, but I think SoNo might be a little bit more appreciative
Just my .02. Of course I would do anything I could to help make this happen.