The best times I ever had at an OTB was the restaurant version on 2nd Avenue. A lot of us were regulars and we had a lot of fun between races, betting who knew the most about various Broadway shows -- and other trivia. My most memorable day involved the waitress asking if another person could sit at my two top, because there were no other seats available. I said "sure" and she brought Jimmy The Greek over to sit with me. I had a good day with 6 winners on the card...and The Greek got skunked. After the 8th race he looked at me and said "I shudda been following you today."
Lots of fun at that place.