The second or third weekend in July is time for the Yates County Fair. (call the phone number below for exact dates and details for this years fair). It starts on a Wednesday and ends Saturday evening.
This is a typical agriculture-based county fair with cooking exhibits and contests; 4H exhibits with blue ribbons awarded; carnival rides and side shows and win-me-a-teddybear booths. There are plenty of crowds and lots of good things to eat (sugar waffles, taffy, candy apples, hots, italian sausage,etc.etc). There is even an antique show at one end of the fairgrounds.
Most of the exhibits take place during the day and the entertainment and rides occur mostly after 6pm (usually until 10pm).
There is a short parade and a queen is selected. Events include live music, rooster calling, tractor pulls, pig races, face painting for the kids.
to get there:
Old Route 14A
Definitely be prepared to buy a shotgun and gunrack for your pick-up truck.
No, really, most Penn Yan people are friendly. If you are just visiting for a weekemd, you might really enjoy your time in Penn Yan.