In Winter Park theres a place that does taco tuesdays. Pretty fun bar. Most of winter park is spread out, so it's not like a town where all the bars are walking distance from each other. The pizza place there is famous too, sorry I'm blanking on names. They have stappled dollar bills all over the joint.
Plus fucking one on Pepporoni's, the people there are dope. This one lady always took care of us and hooked us up fatty. My buddy has like 5-6 mugs there. She used to charge us for like 4 beers when we had 8, or would toss us the end of a keg when it was running low, or buy us a shot when it was slow, etc. Sit AT the bar, not in the seating area. Way better experience.
Went to Winter Park last year for NYE, it was bomb. Make sure you hit the bar at the bottom of Mary Jane for the Mug club speciel, I think it was at 4pm everyday. Met some friendly locals and the bartenders were dope, gave me the "employee" discount.