Day 1:
Golconda, Anna, Cobden, Alto Pass, and Pomona
Kick off your Southern Illinois trip on a sweet note in Golconda at The Chocolate Factory (IM), a popular community shop that specializes in a wide variety of gourmet chocolates, fudge and ice cream. Once you’ve enjoyed some sugary goodness, head to nearby Tanglefoot Ranch, an expansive family-owned farm that features row crops, a peach orchard, a cow herd and freshwater shrimp across 950 acres.
After you’ve taken in the pastoral beauty, cruise over to C’s Bees (IM) in Anna to sample some homemade honey and peruse one-of-a-kind handmade products like whipped honey, hot honey and beeswax candles. Feel free to wander over to Annabelle Market, where you’ll find an assortment of treasures made by local vendors (including a selection of lavender-based, handmade personal care goods from Shawnee Hills Lavender (IM). If you're in the area during May or June, you can also pick freshly bloomed lavender at the Shawnee Hills Lavender farm.
By pairing fresh sandwiches and refreshing salads with a cozy, inviting atmosphere, HeBrewz CoffeeHouse in Jonesboro offers a convenient spot to stop for lunch. Or, if barbecue and burgers are more your speed, try Dixie Barbecue across the street.
Next, mosey on over to mother/daughter-owned Rolling Oak Alpaca Ranch (IM) to bond with some llama-like mammals who are as friendly as they are adorable. Learn about these fascinating animals, feel their soft fleece, then shop the store for expertly crafted products like yarn, soaps and socks.
Southern Illinois is renowned for its local winery scene, and it’s time for you to discover why. Cobden’s Owl Creek Vineyard Winery & Cidery (IM) produces and bottles all its wines and ciders onsite using local ingredients, and the result is a treat for your taste buds. Woodsy and inviting, Pomona Winery (IM) stands apart by cultivating its award-winning wines with locally grown fruits—none of which happen to be grapes. Alto Vineyards (IM) is one of the state’s oldest wineries, with a glorious outdoor deck that offers both breathtaking views of the property and live music performances on the weekends.
Alas, you won’t have time to hit every spot, but if you’d like to venture deeper into the world of viticulture and vines, keep the The Shawnee Hill Wine Trail and its 11 award-winning wineries in mind for a future trip. Situated along a 35-mile scenic drive in the Shawnee National Forest, the views are just as impressive as the wine and hospitality.
If, at this point, you’re looking for an authentic Southern Illinois dining experience, you’re in luck. Arriving at Peach Barn Cafe in Alto Pass is like stepping into a storybook—the charming rural property is set against the backdrop of rolling hills and majestic trees. Plus, the food is exceptional, with fresh, in-season dishes like goat cheese pasta and strawberry cheesecake for dessert.
After a day replete with adventures, it’s time to rest your weary legs at Davie School Inn in Anna or Shawnee Hill Bed and Breakfast in Cobden. The former is a schoolhouse dating back to 1910 that allows guests to experience a different era—each spacious suite features original chalkboards and bookcases from scholastic days gone by. The latter offers a nice chance to escape from city life and relax on a private deck amid a beautiful forested landscape.