Bustling Highlands is an Easy Escape from Sarasota

The charming hamlet is filled with boutiques, fine restaurants and antique shops.

By Ilene Denton April 18, 2016 Published in the April 2016 issue of Sarasota Magazine

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 The charming hamlet of Highlands (elevation 4,118 feet) was founded in 1875, but it really took off when Atlanta golf legend Bobby Jones and his pals “discovered” it in the 1930s and founded Highlands Country Club to satisfy their love of the game. A two-and-a-half-hour drive straight up U.S. 23 from Atlanta, Highlands in-season is packed with old-money Atlantans (heirs to the Coca-Cola fortune, for example) and Floridians—more than a dozen Sarasota families have homes in the development of Wildcat Cliffs alone.

What differentiates Highlands from nearby Cashiers is its bustling Main Street, filled with boutiques, fine restaurants and antique shops. The nonprofit Highlands Playhouse, founded in 1938, is the oldest theater in North Carolina; it presents plays and musicals each summer, and recently added a one-screen movie theater—a first for the region. The newish Bascom Center for the Visual Arts is open year-round; besides exhibits by regional and national American artists, it offers classes in pottery, photography, woodturning and more. And many a pleasant weekend evening can be spent at the venerable Scudders Gallery’s antique auctions.

Sarasota general contractor Jon Swift bought a white clapboard summer home on Chestnut Street in downtown Highlands 20 years ago with his family. He spends summer days playing golf (“I’m not very good at it, but luckily I’ve found somebody up there to play with who’s just as bad as I am,” he says); hiking nearby Glen Falls or one of another 20 favorite nearby trails; and puttering in his woodworking shop. “I have several bird feeders; the squirrels and I fight over them,” he says, “and every once in a while we get lucky enough to see a black bear walk through our yard.” Paradise.

Places to Stay

Like Cashiers, there are lots of privately owned rental properties and companies that manage them. Or indulge yourself at the Old Edwards Inn and Spa on Main Street. TripAdvisor named it the No. 5 top hotel in America in 2015. 

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Where to Eat

Wild Thyme Gourmet, 343 Main St.; American cuisine with an Asian twist.

Wolfgang’s Restaurant and Wine Bistro, 474 Main St.; chef Wolfgang Green is the former executive chef for the owners of Commanders Palace in New Orleans.

On the Verandah, 1536 Franklin Road; fine dining on the banks of Lake Sequoyah.

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