Uncontrived Quaintness

It was 1857 when Becky Roper Stafford's great-great-grandfather first glimpsed Lake Apopka. W.C. Roper was riding through the backwoods of west Orlando" target="_blank">Orange County on horseback, seeking a place to build a home for his family waiting back in Merriwether County, Ga.

Roper bought 600 acres along the shore, between present-day Winter Garden and Oakland, and returned a year later with his wife and 10 children. The ambitious settler operated a sawmill, a grist mill, a sugar mill and a cotton gin. Later he built a tannery for making shoes, and served as Orlando" target="_blank">Orange County's superintendent of schools from 1873 to 1877.

Fast forward to the 1920s, when Roper's son Frank planted the area's first orange trees, marking the humble beginnings of an industry that would sustain and define Winter Garden, which had been incorporated in 1903, for the next six decades.

It was a busy time for Winter Garden's three-story Edgewater Hotel-now a bed-and-breakfast-which opened in 1927 with a telegraph office, electric heating and a fire sprinkler system. As the only hotel in the western portion of the county for nearly 30 years, the Edgewater emerged as a primary community gathering spot; a place where special events were held and business deals were sealed.

Winter Garden remained an idyllic small town throughout World War II and into the 1950s and 1960s. Far removed from Orlando-which was about to be reshaped by the advent of Disney World-the city remained self-sufficient and unpretentious.

"I grew up with the scent of orange blossoms," says Stafford, whose father Bert was also a prominent local citrus grower. She remembers when Davis' Pharmacy was the place to meet friends for a vanilla Coke and when the Starlite Drive-in attracted weekend crowds of teens and families alike.

"Winter Garden was the quintessential vibrant small town," says Stafford. "We had the distinction of being the only town with two train depots because it was such a busy shipping community with fresh fruit going all over the world."

Fast-forward again to the 1980s, when devastating freezes destroyed thousands of acres of citrus. Roper Growers Cooperative, Heller Brothers and Louis Dreyfus Citrus eventually recovered. But as growers regrouped or retreated, once-bustling downtown Winter Garden became a virtual ghost town.

Then developers began buying up decimated groves for new homes, creating new subdivisions seemingly overnight. But most of the residential growth-and the retail growth that followed-was outside the city, which made Winter Garden proper even more of an anachronism.

Then came a brilliant project called Rails to Trails, through which abandoned railbeds across the country were converted into hiking and biking trails. The popular West Orange Trail passed directly through Winter Garden, thus converting the all-but-forgotten city into an oasis to thousands of ready-to-spend strollers.

"Rails to Trails has been an incredible catalyst," says Stafford, who now works with the Winter Garden Heritage Foundation to keep rekindle her hometown memories. "All of a sudden, we had 10,000, then 20,000, now 50,000 people a month coming through downtown Winter Garden."

City officials have made certain that these visitors will be charmed by what they see. In 2001, the tired downtown district underwent a facelift during which brick streets were restored, old buildings were remodeled and Centennial Fountain, saluting the city's citrus-growing heritage, was constructed.

Today locals and outlanders gather at Choctaw Willie's in the reopened Edgewater Hotel for barbecue, collard greens and sweet tea. Across the street, Moon Cricket Café serves eclectic cuisine and an array of micro-brewed beers. Winter Garden Pizza Factory is all about pasta, fresh pies and family fun.

Proprietor-owned shops, like JR's Attic, Downtown Herb Shoppe and Every Little Girl's Dream, are thriving. But you'll still find a wonderfully cluttered hardware store that sells farming supplies, which serves as a reminder that this town quaintness isn't contrived.

And, locals proudly note, Winter Garden features two historical museums open seven days a week. There are the Central Florida Railroad Museum and the Heritage Museum, both housed in restored depots. History buffs may also stroll around the city and view such landmarks as the Beulah Baptist Church, originally built in the 1860s.

"Winter Garden has reinvented itself," said MaryAnne Swickerath, editor of the West Orange Times, established in 1904. Swickerath has covered the city for a quarter-century, and says she delights in its new joie de vivre. "There's a new spirit," she notes. "There are a lot of new residents with a lot of new pride."

And redevelopment is on a roll: Stafford is hard at work with the Winter Garden Heritage Foundation to renovate the historic Garden Theater on Plant Street. The old movie house, which will become a 300-seat performing arts center, is set to reopen in 2005.

"The progress made in the last five years has taken Winter Garden back to being the booming community it once was," says Stafford.

But Winter Garden enters it second century facing unprecedented challenges. Within the city limits, residential building permits jumped from 522 in 1999-2000 to 769 in 2002-2003, according to City Manager Hollis Holden. The population has doubled from the mid-'90s, making Winter Garden one of the fastest growing cities of its size in the state of Florida.

And just south of the city, the 38,000-acre Horizon West master-planned development is under way. Horizon West, with an Americana theme, will ultimately contain homes, schools, recreation facilities and village centers not unlike downtown Winter Garden.

How, then, will this city of 20,378 retain its folksy charm while accommodating tens of thousands of new residents?

"Winter Garden has a small-town heritage and it's our intention to preserve that despite significant and rapid growth," says Holden. "We have a strong commitment to preserving and revitalizing this historic town."