Winter Park

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Winter Park is where the rich people live, play golf and get buried. Park Avenue is the prettiest shopping district in Orlando, with a small park, band shell and working train on one side, and tiny shops on the other, many local. Great outdoor dining. Don't miss Palamano's Coffee shop: outdoor seating, free wifi and very empty. Try Gurtzberry if you have the $$$. Tatame bar hosts the monthly Dr Sketchys Anti-Art School sketch/drink night. Avoid Mead garden until its returned to its former glory. Orange Avenue is where you go to drink coffee at a Christian coffee house, see performance art at Frames Forever, watch a high-priced cabaret show at Winter Park Playhouse and buy tile and countertops for your house at one of several stores. And there's a Goodwill. The best part of Winter Park is the drive through the neighborhoods of homes, though the brick streets make for rough riding.

In March the annual Winter Park Sidewalk Arts Festival brings 300,000 people into the park next to Park Avenue over just three days. Been going on for 50 years. A must-see. In April, the Taste of Winter Park, a 24 year tradition, gets you the best food in town for $45.