Get to know Winter Park

People who live in Winter Park will tell you that Winter Park is not Orlando, that it is its own thing. Though the uninitiated may only notice a change in the color of the street signs, there is a very real attitudinal difference between the two cities. Winter Park is as old as the metropolis to its south, but it has denied itself growth in the service of charm, and that means there’s no more pleasant city in the metro area. Winter Park is brick streets and live oak trees, twee little bakeries serving obscure Portuguese pastries and carefully curated designer boutiques where well-behaved dogs are not only welcome but expected. Homes range from textbook midcentury Florida ranch to gigantic lakeside mansions — the latter coming in two varieties: century-old brick estates and architecturally significant modern masterpieces. The most sought-after properties are on a chain of lakes linked by canals, or within walking distance of Park Avenue, the brick-and-boutique-lined heart of downtown.

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Winter Park History & Culture

Winter Park — as the name might tell you — was conceived as a resort community, right about the time the railroad came through. The lakes and ancient, moss-laden trees made for a storybook setting, and it became a place of retreat for those fleeing northern winters (at least the subset that didn’t care for the beach). The chain of lakes created a boating culture that continues to this day. Winter Park is a city that loves it gardens and its museums, of which there are many. The civic calendar is full of farmer’s markets and art fairs, and the laid-back party atmosphere that was present at the city’s founding is still there today. Most of the people who live in Winter Park seem to think it’s the best place on earth — and are insistent that you don’t confuse it with Orlando.

Winter Park Dining & Shopping

If “Dining & Shopping” were not the heading of this section, it might do as the motto of the city of Winter Park. There’s an incredible array of chef-driven restaurants here, many of them award-winning, and the whole town treats dining out like a religious observance. Locals will even dress for dinner, at least by Florida standards. Beyond the high end, the area bristles with dozens of small local cafes, refined chain eateries, and diners and fast food and coffee shops that all — even the Popeye’s — seem ironically hip. The best boutiques line Park Avenue, surely one of the south’s premier retail strips. But there are dozens of other shopping centers in town, and there’s often a locally owned gem taking up a tropically colored bungalow on a side street. While Orlando is full of big-name boutiques, there’s rarely a reason for a Winter Park fashionista to leave the city limits.