I entered a quilt into our county fair a couple years ago - I did it purely as a challenge to myself, and I didn't expect to win anything as the quilt I entered had a pretty simple construction and machine-sewn bindings, and the category I entered was one of the largest categories. I was happily surprised to get a 4th place ribbon! It wasn't judged, exactly, but they did write some nice comments on the back of the name-tag they put on it. It was chosen because they really liked the color arrangements I did.
I would have been happy without the ribbon or the nice comments, but I have to admit it made me feel pretty good to win a ribbon and have some compliments. I was proud to just have my quilt on display at the fair though - I feel like I "take" so much from the quilts I look at every year at the fair, it was my turn to contribute something. It was fun to have coworkers come to me and say they'd seen my quilt (the fair puts your name on it in huge letters) and tell me stories of their aunt or grandmother who was a quilter. It was a nice conversation starter.
I haven't entered again since, I should, though. It's good to contribute!
I've let my guild membership lapse but I still attend the show my (ex) guild puts on every summer. There are no prizes for the quilters there, it's all about putting on a good show. There's a back room where people bring in antique quilts for display, some with family histories, some with just big question marks. My guild joins with 2 other local guilds for the show, so there's always lots to look at. It's a really good show, I feel lucky that it's practically in my back yard! (It's held about 2 miles from my home!)