I guess I would pick Wolftrap in Virginia as one of my favorite venues. We played there nearly every year, usually with The Smothers Brothers. Sound was always excellent there - never a problem with any aspect of that. The crowds were always sold-out and everybody in the audience was there for a good time. There were the high-priced seats under the pavillion cover, but the "cheap" seats on the lawn were pretty cool too.
There were other venues that were also quite fun to play. The Kennedy Center was one. And I should also mention The Britt Festival here in my new/old hometown. "Atmosphere" there was always pretty electric, with many of my old classmates and teachers in the crowd. It's also an outdoor venue similar to Wolftrap but smaller.
Worst venues: the Roy Radin tours when I was with The Brothers Four. Mostly military bases and the NCO club shows in the afternoon were the pits. Imagine the Brothers Four in the 1970's trying to entertain a bunch of 20-year-olds! The sound system was an ancient Shure system with two 4-foot column speakers.
Then there was the high school auditorium that The Kingston Trio played once. George and I showed up for sound check to find that the sound techs were high school students who didn't have a clue. The sound booth was in the clouds at the back of the auditorium and I had to climb a ladder to get up there and set the sound for these poor kids as George tested the mics. I told them "don't touch a thing unless there's some feedback and then only dip the master volume slightly to relieve it." Luckily they kept their hands off the board after I'd set it and we made it thru the show OK.
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