Becky Schneider pours a taste of Golden Oak Aged Reserve in the sun-washed tasting room at Pomona Winery near Alto Pass, Illinois, and watches as Anne Pitts sips it. “I used to have a problem calling wine creamy until this one,” Becky says, grinning as a familiar look of wonder spreads across Anne’s face and adding, “I’ve never tasted anything like it. I steam a lot of veggies in it; I throw it in pasta sauces.”
Anne, who’s toured California’s Napa and Sonoma valley vineyards, slowly shakes her head. “Even after a few seconds, it’s still buttery,” she says in amazement.
Becky just smiles and continues the $3 taste tour of 10 wines at Pomona, one of 12 wineries on the hilly, wooded Shawnee Hills Wine Trail (110 miles southeast of St. Louis). She pours a sample of Orchard Harvest, which she likes to add to chicken noodle soup. The Orchard Spice is like apple pie in a glass, and it’s great in white chicken chili, she says. She also drizzles the strawberry dessert wine on fruit salads and into brownie batter.
Seth Blickhan, sales manager at nearby Alto Vineyards, shares cooking ideas during tastings, too. A Spanish-style sangria warming in a slow cooker makes a house smell like Christmas, and Alto’s dark red Norton has a mint finish that pairs beautifully with lamb chops. Cooked down, cherry wines make an amazing pork chop braising liquid, and the Chancellor spikes burgers ready for the grill.
Spend even just a little time among these family-owned wineries nestled in Shawnee National Forest, and you’ll feel a welcome tug: Do you go home with bottles of wine in tow and start cooking, or do you linger with a glass and watch the sun set over a vista stretching more than 35 miles?
Most people stay on the trail awhile, because these little towns—not a stoplight among them—along the Shawnee Hills Wine Trail offer enough to fill several days. Fresh-picked apples fill baskets at Rendleman Orchards’ Farm Market, and apple dumplings tempt at Flamm Orchards. Walking trails around Cedar Lake cross creek shallows; hilly hikes through Little Grand Canyon and Giant City State Park shred stereotypes about Illinois’ landscape. Dozens of bed-and-breakfasts and cabins burrow in the hills, and the wineries reveal personalities all their own—not to mention a mix of sweet and dry varieties reflecting the region’s deepening understanding of wine making.
“The past few years, people have become much more open-minded about wine,” says Brad Genung, winemaker at Owl Creek Vineyard near Cobden. “And presentation is really important, giving folks a really good experience. It’s not like the old days, when people would come in and taste and buy a couple of cases. [So] on Saturday afternoons, we have live folk and bluegrass. That kinda makes the place a little stickier.”
Darkness falls on Rustle Hill Winery, known for its rustic pizzas, panini and lakeside amphitheater. A few dozen people sip wine and listen to Eli Tellor, a 23-year-old Anna native hoping to record his first album (Nashville’s country scene and Memphis’ blues bars lie just three hours south). He eases effortlessly from “Ring of Fire” to his own “Bye, Bye Baby” at the request of Patrick Lee Beasley, a Southern rock singer who has left the honky-tonks behind to perform here. To him, the wineries are like wine itself: They get better with age. One hundred years from now, the Shawnee Hills Wine Trail will rock with visitors, Patrick says. Jo and Rich Crackel of Mattoon, Illinois, staying nearby at the stately Historic Bell Hill Mansion, hope he’s wrong. They used to live in Napa—“before it became commercialized”—and their quest for interesting dry Cabs and Chardonnays spurred this first trip to southern Illinois. But the area’s quiet beauty and empty country roads will keep bringing them back.
Click to the next page for our three-day itinerary.
For more info: Southernmost Illinois Tourism Bureau. (800) 248-4373; southernmostillinois.com 
Start by visiting the Shawnee Hills Wine Trail website and downloading a map of the wineries (shawneewinetrail.com ). A GPS will help, but the route has good signage. The area stretches about 30 miles across, but because of all of the backroads, 4 miles can take 20 minutes.
Each winery provides a list of wines, from dry to sweet. Some offer food, too. The special cheesy-garlicky bread-and-oil appetizer at Blue Sky Vineyard is divine. (618) 995-9463; blueskyvineyard.com 
The grapevine-smoked brisket sandwich at Von Jakob comes with rustic potatoes and a mixed-green salad topped with Red Oak port vinaigrette. (618) /893-4600; vonjakobvineyard.com 
A hike through Little Grand Canyon takes about two hours. (800) 699-6637; fs.usda.gov/shawnee 
Refuel in Anna with dinner at Brick House Grill, which tops filets with thick blue-cheese gravy. (618) 833-5367; annabrickhousegrill.com 
Antique furnishings and Southern hospitality and cooking await at Historic Bell Hill Bed and Breakfast in Cobden. (618) 697-0326; historicbellhill.com 
Girlfriends love the new Alto Wine Trail Loft—a two-bedroom vacation rental in an Alto Pass historic building. (618) 698-7474; altowinetrailloft.com 
The Davie School Inn stuns with classy decor and in-room breakfasts in a rescued Anna elementary school building. (618) 833-2377; davieschoolinn.com 
Apple-cider doughnuts and fresh-picked Jonagolds make a great snack at Rendleman Orchards’ Farm Market in Alto Pass. (618) 893-2771; rendlemanorchards.com 
A quick walk around Cedar Lake or a ride in a rented motorboat along Little Grassy Lake offers a quiet start to the day.
Yellow Moon Cafe in Cobden serves vegan dishes such as pumpkin soup made with coconut milk, and the carved turkey and cranberries come on wheat berry bread. (618) 893-2233; yellowmooncafe.com 
Wine tastings easily fill another afternoon; plan to end at Rustle Hill Winery and enjoy the thin-crust veggie pizza and live music. (618) 893-2700; rustlehillwinery.com 
Towering rock formations gave Giant City State Park its name, and a 45-minute moderate hike winds through them. Stop at the visitors center in Makanda for trail maps and to catch a 20-minute film about the park’s history and ecology. (618) 457-4836; dnr.illinois.gov 
A hike means you won’t feel so guilty when you indulge in a flaky apple dumpling from Flamm Orchards in Cobden. (618) 893-4241; flammorchards.com 
As you head home, stop for lunch at the 17th Street BBQ in Murphysboro. The barbecued meats and baked beans are legendary, and the decadent banana pudding is served in a Mason jar. (618) 684-3722; eat17bbq.com 
In Carbondale, the General Store at Walker's Bluff offers great shopping, with kitchen items and gifts. (618) 985-8463; walkersbluff.com 
(A version of this story appeared in Midwest Living® September/October 2012.)