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BARRETT ROCHMAN, a Chicagoan by birth, made money as an undergrad at Southern Illinois University (SIU) in the 1960s by selling hand-delivered birthday cakes (complete with song) to students at SIU and then expanded into sandwiches — hence, his Munchie Man nickname. His fortune, though, comes from real estate, including buying distressed properties in tax sales. Since 1972, he’s owned property near Cobden, Ill., that son-in-law Jim Ewers was using to raise grapes.

When they decided to build a winery, Rochman wanted to do it in a big way. His motivation, he says, was to leave a legacy. “Some people build a pyramid,” he says. “I built a winery.”

Rochman, now 67, pumped more than $3 million into producing a faux-17thcentury Tuscan villa — replete with stucco made to look weather-beaten, a clay-tiled roof, stone arches, giant oak double doors and a 35-foot carved bar — and filled it with his art and antiques. There were two bed-and-breakfast suites, a large facility for weddings and other events, a lake, a waterfall and outdoor sculptures.

Rochman’s Blue Sky Vineyard, which opened in the summer of 2005, dwarfed the other Shawnee Hills wineries, and it immediately became an 800-pound gorilla in a group of chimps. At first, Rochman didn’t know a thing about wine, something he freely admits, though he says he’s evolving. (“My palate’s getting better,” he says.) Some were upset that Rochman started offering beer and mixed drinks at the winery. (“My idea of a winery is very different than what Blue Sky is,” says one of the old-timers.) Some even suggested that Rochman had an edifice complex. (“His ego likes this building,” says a friend.)

The grousing, however, was overshadowed by the fact that Rochman’s investment was noticed — the publicity garnered by Blue Sky helped draw more visitors to the region. Suddenly, lots of people wanted a piece of the action.

Gerd and Anders Hedman, transplanted Swedes who owned a small vineyard and a small peach orchard in Alto Pass for many years, began bottling their own wine and serving Scandinavian-themed meals. Their cozy Peach Barn Café, which also does double duty as Hedman Vineyards’ tasting room and gift shop, is the place for people who have a hankering for pickled herring, lingon-berries and Swedish meatballs. Anders boasts that his vines grow on the highest elevation in the region, second only to Bald Knob Mountain.

Gary Orlandini, who moved to the region in 1966 from northern Illinois and stayed to get away from cold winters and fl at prairies, planted about four acres of chambourcin and vignoles on his farm in 1988 and christened the facility Orlandini Vineyard. Two years ago, he built a large tasting room and joined the wine trail. A friendly, plainspoken bear of a man, Orlandini says it’s been a happy decision. “Running a winery is an owner-friendly business,” he says. “You get to make money, enjoy nice hours and meet nice people.”

Other newcomers are refugees from big city and corporate life. The year Blue Sky opened, Scott Sensmeier, who left an information-technology job in Atlanta after 12 years, and his wife, Kate, bought a small winery near his hometown of Cobden, renamed it StarView Vineyards, built a new facility for visitors and increased the vineyard acreage.

That same year, Brad Genung, a former equity research manager for a St. Louis–based investment firm, bought Owl Creek from Wichmann, who never really liked the marketing side of the business. Genung says he developed an interest in the wine business in the mid- 1990s, and the more he learned, the more he became convinced that Shawnee Hills was the place to be. “I studied the soil and climate and decided that at some point this is all going to pop,” Genung says. Buying an established winery with Owl Creek’s reputation was, he says, a “no-brainer.”

And in early 2006, Jim and Barb Bush, retired phone company executives from Chicago, acquired Kite Hill Vineyards. They’d scouted the country from Hawaii to Kentucky looking for the ideal place to operate a bed-and-breakfast and, to their surprise, fell in love with southern Illinois. They made an offer and found out the adjoining winery and vineyard were for sale too. They were unprepared for the volume of business they immediately attracted — the first year, all of their wine sold out earlier than they had expected. “We know we have to expand,” Barb says.

Among the newest entrants into the local winery business are John Patrick and Debbie Russell, who opened Rustle Hill Winery on Highway 51, smack-dab in the middle of the wine trail area and closer than their competitors to Carbondale and its thousands of SIU undergrads. Though Rustle Hill produces and bottles more than 6,000 gallons of wine a year, it feels more like a wine-themed entertainment complex than a winery, packing people into its chalet-style main building that boasts a deck overlooking a lake, an amphitheater and a couple of luxury cabins that can be rented by the day. The atmosphere here on a typical Sunday summer afternoon is southern Illinois casual: college girls in tank tops and shorts, middle-aged couples in khakis and pastels and weekend bikers sporting sleeveless tees and do-rags. The chances of crossing paths here with a wine snob are slim to nonexistent.