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24 Hours in Winter Park

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Winter Park was born when two wealthy New Englanders fled their northern homes to seek solace in sunny Central Florida. When Oliver Chapman and Loring A. Chase purchased the land for $13,000, they set out to build Florida’s first “planned community” catering to winter homes for affluent Northerners like themselves. The founders envisioned a city buzzing around a downtown park and its main street, Park Avenue. In the century to come, Winter Park blossomed into the cosmopolitan city it is today. Now, it is where many of Orlando’s top professionals retreat home from their offices and into the suburbs.

WATCH THE WORLD GO BY ON PARK AVENUE

As Chapman and Chase destined, Park Avenue is the center of attention in Winter Park to this day. It is said to be the heart of the city, featuring more than 140 boutiques, three museums, a golf course and an 11-acre park. Park Avenue’s brick streets lined with charming storefronts, al fresco dining and colorful awnings give a sophisticated, European feeling in the small Florida town.

SHOP FOR UNPARALLELED FINDS

International brands join homegrown boutiques for a first-class shopping experience on Park Avenue. Shop the likes of Lilly Pulitzer and Ethan Allen next to whimsical niche stores. Scour for holidays gifts you won’t find in any mall at a plethora of boutiques, such as the Partridge Tree Gift Shop.

Plus, pick up something for man’s best friend from The Doogie Door’s treat bakery! For a true initiation into the shopping scene, visit on a Saturday morning for the Winter Park Farmers Market. Named the best produce and plant market in Central Florida, you’ll shop at the location of the historic old train depot for the freshest local offerings.

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