Start by visiting the Shawnee Hills Wine Trail website and downloading the map of the wineries (shawneewinetrail.com). The area is only about 30 miles wide, but because of all of the backroads, 4 miles can take up to 20 minutes to drive.
Wines made from apples and berries star at Pomona Winery.
The grapevine-smoked brisket at Von Jakob comes with a mixed-green salad topped with Red Oak port vinaigrette.
A hike through Little Grand Canyon works up an appetite for dinner at the Brick House Grill in Anna; try the filet topped with blue cheese gravy. The Davie School Inn has turned a 1910 elementary school into a posh B&B (from $85), and the Historic Bell Hill Bed and Breakfast in Cobden celebrates Southern hospitality (from $150).
After a leisurely B&B breakfast, head to the tasting room at Owl Creek Vineyard for some of the trail’s best wines.
Flamm Orchards sells killer peach cobbler, and Yellow Moon Cafe dishes locally sourced and seasonal soups, salads and sandwiches.
Wine tastings fill an afternoon: Our favorites include famed Blue Sky and Alto Vineyard.
Plan to end at Rustle Hill Winery to enjoy the thin-crust veggie pizza and live music in the lakeside amphitheater.
More Information: (800) 248-4373; southernmostillinois.com
Add a day
The 17th Street BBQ in Murphysboro serves legendary smoked meats, baked beans and decadent banana pudding in Mason jars. The classy General Store at Walker’s Bluff in Carterville teems with kitchen items, gifts and candies that make memorable souvenirs. A 45-minute hike winds through towering rock formations that gave Giant City State Park in Makanda its name.
Bring the kids!
Cobden Peach Festival Small-town Americana meets summer-sweet, locally grown peaches in Cobden. Families will love the annual festival—held on the first Friday and Saturday every August—with its downtown parade, carnival rides, Peach Queen contest and fresh cobbler. (618) 893-2425; southernmostillinois.com
Five great places to explore nature
1 Cache River State Natural Area The boggy swamp in Cypress looks like something you’d expect to see much farther south. A boardwalk snakes into the swamp for an up-close view of the massive cypress trees. (618) 657-2064; dnr.state.il.us
2 Cedar Lake An easy hike around this calming reservoir outside Carbondale offers a simple, beautiful and quiet place to commune with surrounding fauna and flora. southernmostillinois.com
3 Cave-in-Rock State Park A 55-foot-wide mouth lures explorers into the namesake cave’s cool limestone belly, all near the Ohio River town Cave In Rock. (618) 289-4325; dnr.state.il.us
4 Tunnel Hill State Trail This 45-mile trail gets its name from the narrow tunnel it passes through. Bring your bike to ride the former train route past flat farmland, wooded bluffs and wetlands. (618) 658-2168; dnr.state.il.us
5 Giant City State Park Daily horseback trail rides (available March through October) weave through the outstanding scenery in this popular park near Makanda. (618) 457-4836; dnr.state.il.us