I'm pretty sure Bob Gibson recorded "Tell Old Bill" for Riverside sometime around 1960. If not there, then on the Vanguard recordings of the 1960 Newport festival. Odetta recorded it later in a lower key. I've got 'em on LP buried somewhere.
As for music in the village in the late '50s - early '60s, my favorite hangouts were Gerde's on Monday nights and Washington Square on Sunday afternoons. There was also some nifty music at the Henry Street Settlement House on Saturday nights. For a while John Herald was hosting a late night sing at a place on Broadway in the twenties. A lot of us also used to do Billy Faier's radio show from time to time. 'Twas on WBAI from midnight to 6 a.m. on Saturday nights.