The busiest station operated by SunRail, the region's commuter-rail service, is in the heart of Winter Park. The charming Craftsman-style building (above), located near the intersection of Morse Boulevard and Park Avenue, is where thousands of visitors arrive from across Central Florida every year. Amtrak passengers also embark and disembark here. Many of those visitors find themselves exploring downtown's various nooks and crannies, such as the eclectic shops of Greeneda Court (left) and the Hidden Gardens.
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West, downtown O’do — they all outfunk us. By a long shot. But when it comes to sheer livability, hands down, it’s Winter Park. Winter Park is an island in a sea of sameness. Of all the other “Parks” hereabouts — College, Thornton, Baldwin, Theme, etc. — it’s the only one that’s incorporated, and thereby officially delineated (physically and psychically) from Central Florida’s sprawl. Now marking 130 years since its incorporation as a city, Winter Park has cemented its standing not only as a place more special, but as a center of influence and affluence of far greater regional impact than its population (about 29,000 residents) might suggest. It has been that way throughout the city’s history, which is so entwined with that of Rollins College that it’s often difficult to remember which came first, the college or the city. While the first permanent residents settled here in the 1850s, it wasn’t until 1880 that the area began to flourish, thanks largely to the expansion of the South Florida Railroad and the arrival of Chicagoan Loring Chase and his business partner, Oliver Chapman, from Massachusetts. They bought 600 acres along the chain of lakes with the purpose of creating, as one newspaper of the time reported, “a first-class resort of Northern and Southern men of wealth, where amidst orange groves and beautiful lakes and luxuries that every enterprise and wealth can devise and command, a L I V I NG I N WI N TE R PAR K