Winter Park was founded as a resort community mainly by northern business magnates in the late 19th and early 20th centuries. Its main street includes civic buildings, retail, art galleries, a private liberal arts college, museums, a park, a train station, a golf course, a historic cemetery, and a beach and boat launch to the famous Winter Park Chain of Lakes.
Its close proximity to Downtown Orlando along with its Chain of Lakes has made this a favorite place for local residents. The beautiful downtown area with beautiful shops and boutiques offers a wonder day of shopping and dining. The large park and rail road station give it a small town feel where people appreciate just being outside to enjoy the Florida weather.
The Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest juried outdoor art festivals, rated among the top shows by Sunshine Artist and American Style magazines. In 2012, about 1200 artists from around the world applied for entry and an independent panel of judges selected 225 national and international artists to attend the show. The all-volunteer board of directors runs the annual festival, now in its 50th year.
Winter Park is one of those towns you need to take a day and explore by bicycle. It has brick streets, old oaks, and a variety of homes from small bungalows to huge lake front mansions. Having breakfast on Park Avenue on Saturday morning and watching the world pass by is a must do for experience.
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