Southern Illinois is a beautiful and diverse region that blows my mind! I didn’t know such a place existed in the Midwest until I visited the Shawnee National Forest, Garden of the Gods, and, most recently, the Shawnee Hills Wine Trail. Yes, that is the Garden of the Gods in Illinois, not Colorado. But it looks just as good! Southern Illinois is unique, from the Shawnee National Forest’s rolling hills to the Mississippi River’s vibrant cities.

Nature lovers will find exploring the Shawnee National Forest is similar to what you would find in Colorado. The forest is over 280,000 acres of rolling hills, dense forests, canyons, bluffs, streams, and waterfalls. You can enjoy hiking, camping, fishing, and boating in this beautiful natural setting and the state parks within the Shawnee National Forest.

Southern Illinois is an excellent place for art and culture lovers. The region is home to several museums, art galleries, and theaters. Visitors can also enjoy a variety of music festivals and other cultural events throughout the year. Foodies and wine enthusiasts will be delighted by the many culinary options and the Shawnee Hills Wine Trail in Southern Illinois. The region is known for its wineries, barbecue, and other comfort foods. 

Disclaimer: Blog posts may contain affiliate links and ads. If you click on these links, I may earn a small commission. This helps keep the blog running and supports me – at no cost to you. If you have any questions, please read my disclaimer and privacy policy.  A special thanks to Southernmost Illinois for hosting my trip. All opinions in this article are my own.

Discover the Shawnee Hills Wine Trail

The Shawnee Hills Wine Trail is a scenic and fun 40-mile trail that invites wine enthusiasts and nature lovers. This trail encompasses twelve diverse wineries with unique offerings. I’ll share the wineries I visited and their details below. 

Whether you take the wine trail by car or bus tour, you’ll experience different landscapes, charming towns, and friendly hospitality. Many back roads lead the country wineries within the Shawnee Hills area, a stunning backdrop for the vineyards.

Wineries on the Shawnee Hills Wine Trail 

One of the highlights of the Shawnee Hills Wine Trail is the opportunity to savor a wide range of wines made from locally grown grapes. Each winery has its specialties, and you can enjoy tastings and tours and learn about the winemaking process from knowledgeable staff. In addition to the wine, the Shawnee Hills Wine Trail offers a variety of other beverages, foods, attractions, and activities. Many wineries have outdoor seating areas to relax and enjoy the scenery or live music while sipping wine (or a soda!). 

I visited five of the twelve wineries on the Shawnee Hills Wine Trail. Here are the highlights and specific details of each stop:

StarView Vineyards – Cobden, IL

StarView Vineyards is a family-owned and operated winery that opened in 2013. Visitors can also indulge in on-site lodging and celebrate special occasions in their charming events barn. An outdoor deck offers views of rolling vineyards, a bluff, and a pond teeming with colorful koi and turtles that visitors can feed. The spacious tasting room invites guests to try StarView’s award-winning wines while enjoying live music and a cafe menu.

Brett, the owner and winemaker, crafts each wine using grapes harvested from their three acres of vineyards. Among their selection, the Vignoles 2022 (a semi-dry white wine) gained the #1 spot as my StarView favorite. Additionally, their wine slushies are a popular treat that combines their wine with the icy coolness of a slushie.

Wichmann Vineyard – Cobden, IL

Wichmann Vineyard is the latest addition to the Shawnee Hills Wine Trail. Hanna Wichmann, the owner and winemaker, is the daughter of Ted Wichmann, a trailblazer in grape cultivation and winemaking in southern Illinois. The small, family-run winery primarily utilizes grapes grown within the Shawnee Hills region and makes 800-1200 gallons of wine annually. The winery offers a cozy atmosphere, an upstairs tasting room, and a multi-level deck. Visitors are encouraged to enhance their experience by bringing food or picnics; well-behaved, leashed pets are welcome. 

Among the eight wine offerings at Wichmann Vineyard, two wines stood out as my favorites: the Crush Rosé, a semi-sweet rosé wine, and the Traminette, a newer dry white wine. 

Owl Creek Vineyard – Cobden, IL

Owl Creek Vineyard, a family-owned artisanal winery and cidery established in 1980, was acquired by the Genung family in 2005. In 2012, Owl Creek expanded its product line to include Apple Knocker Hard Ciders. Visitors can sample Owl Creek wines and Apple Knocker hard ciders at the winery’s spacious tasting room. The tasting room features a cafe, live music, a large outdoor deck, and a concert stage. All of the wine and cider are locally sourced and produced on-site. The Shandy and Pina Colada ciders stood out as my favorites among the extensive selection of ciders.

Blue Sky Vineyard – Makanda, IL

BlueSky Vineyard offers a Tuscan-inspired oasis that captures the romance of Italy. On 13 acres of vineyards, the estate has stunning views of Shawnee National Forest, a tranquil pond, and a waterfall. The tasting room is designed with stucco walls, hand-hewn beams, Portuguese tiles, and intricately carved doors. BlueSky Vineyard is a haven for wine enthusiasts and a popular destination for special events. The venue offers an event space and on-site lodging to accommodate celebrations of all sizes.

In addition to its award-winning wines, BlueSky Vineyard provides live music, ample indoor and outdoor seating, scenic views, and a selection of non-alcoholic beverages, including sangria. My favorite tasting from the BlueSky collection was the “Eclipse Crossroads,” an estate-grown bubbly rosé created to honor the 2024 Total Solar Eclipse. 

Feather Hills Winery & Vineyard – Makanda, IL

Feather Hills Winery, established in 2018, is a shared dream brought to life by Randy and Renee Feather. With an onsite kitchen, this modern, two-level tasting room offers a unique dining experience featuring gastropub-style food. On-site lodging is available, and large covered decks overlook the vineyard and pond. Children, picnics, and leashed pets are welcome. My favorite Feather Hills wine was the Chambourcin Rosé, an estate-grown, award-winning rosé wine.

Visitors can browse the gift shop, enjoy live music, and stay in the winery’s on-site lodging. Its expansive, covered decks overlook the picturesque vineyard and a pond and welcome leashed pets. The Chambourcin Rosé is my favorite, an estate-grown rosé that has garnered recognition.

Here are some additional details about the Shawnee Hills Wine Trail:

• The trail is located in Southern Illinois, about two hours from St. Louis, three hours from Chicago, and four hours from Indianapolis.
• The trail is open year-round, but the best (and busiest) time to visit is during the fall harvest season.
• Many wineries offer special events and festivals throughout the year.
• Many of the wineries welcome guests to bring their food and picnics. 
• Most of the wineries are child- and pet-friendly. 
• Consider taking the winery trail by hired bus or tour for more accessible travel and to have a designated driver. PLEASE have an assigned designated driver if you plan to drink alcohol. 

Stay at the Davie School Inn: A Unique Lodging Experience on the Wine Trail

In addition to the numerous on-site lodging, hotels, and Airbnb options, the historic 1910 Davie School Inn stands out as the most unique and memorable lodging experience. It is located in the quaint town of Anna, Illinois, in a charming old schoolhouse restored and transformed into a comfortable and inviting bed and breakfast.

Nestled in a former elementary school that served its community for nearly nine decades, the Davie School Inn offers eleven cozy guest suites. Each suite boasts a unique theme, adorned with antique furnishings and vintage touches. Some suites feature original chalkboards, while others have charming reading nooks or private balconies. I enjoyed staying in the “Black Suite,” an American History-themed room with a full-size American flag, a JFK tapestry, and various historical artifacts. The king-sized bed, sitting/dining area, private kitchenette, and jacuzzi tub provided a comfortable and stylish stay.

Accompanied by my travel companions, I was met in the mornings by the inviting aroma of freshly brewed coffee. The owners, who are passionate travel enthusiasts, prepared a delicious breakfast using locally sourced ingredients. After a day of exploration, the inn’s common areas offer us places to rest and relax in the gymnasium leisure area and outdoor patio. The Davie School Inn is an experiential stay that immerses you (literally) in old-school charm.

Winery lodging

• Alto Vineyards – The Alto Loft: 2 bedrooms, 1 bath, sleeps 8, hot tub, and deck
• Peachbard Winery – The Bitty Houses: 2 bedrooms, 2 baths, sleeps 4, and porch
• Von Jakob Winery & Brewery – The Wine House: 3 suites, jacuzzi tubs, bed and breakfast
• BlueSky Vineyard – Winery Suites – 1 bedroom, 1 bath, balcony, breakfast
• Feather Hills Vineyard – Farmhouse Cellars: 1 bedroom, 1 bath, sleeps 2, porch, wine tastings
• StarView Vineyards – Winery Retreat Home: 4 bedrooms, 2 baths, sleeps 8
• Honker Hill Winery – The Lodge: 2 bedrooms, sleeps up to 6, rustic

Nearby things to do:

• Illinois Garden of the Gods: Best Midwest Views
• Visit Metropolis, Illinois: A Superman-themed town
• The Ultimate Owensboro Weekend Getaway
• 8 Reasons You Should Visit Evansville, Indiana

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