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Get to know Winter Garden

Winter Garden is one of those miraculous places that manages to blend small-town closeness with a bustling, vibrant hipness. While some communities allowed themselves to be hollowed out as they grew, Winter Garden filled itself in — making investments in public spaces, keeping a careful eye on new expansion, and going the extra mile to develop a sense of community with rich recreational and retail experiences. There are wide, tree-lined streets in the historic downtown, through which one of the nation’s great bike trails runs. Sidewalk cafés and farm-to-table restaurants spill out on to the brick, and the public plazas are busy every weekend with a legendary farmers’ market, classic car shows, outdoor concerts, and pelotons and parades of two-wheeled locals. Ask a local (who may very well be driving a golf cart to dinner), and they’ll often tell you they came to visit the manicured theme parks, but found themselves living in something even more perfect.

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Winter Garden Commerce & Culture

The heart of Winter Garden is the historic area centered on Plant Street. The West Orange Trail runs through the median strip there, where it’s surrounded by beautiful gazebos, fascinating local shops, quirky galleries, and some of the best dining to be found in a small downtown — all of it decidedly casual. But there’s more to the area than this storybook setting. There’s plenty of other commercial opportunity just to the south of downtown, and one of the region’s largest outdoor malls just a bit further on. Luxury communities surround stunning Lake Apopka, and new highway construction has brought a wealth of developments to the hills of the former orange groves to the south. Winter Garden is the gateway to the “back way” to the tourist areas of Orlando, but it’s valued as a paradise for boating and fishing, golfing and tennis, and a general lack of hustle-and-bustle. Worth a visit: Winter Garden's popular farmer's market (pictured here) convenes on Saturdays from 9 a.m. until 2 p.m., attracting a host of artisans and vendors representing more than 20 local farms.