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Wine, Dine and Shine in the Shawnee Hills

From Local Experts

3 Days 27 Miles


Anna, Alto Pass, the Shawnee Hills Wine Trail, Cobden, Makanda

From the local experts at Southernmost Illinois - Shawnee Forest Country

Gather the gals and get going.

The Shawnee hills of Southern Illinois provide open spaces and relaxation. From walks to wineries, we are sure you will find yourself relaxed and renewed at the end of your stay.


Day 1:


  • 94 year old in front of a wing mural.

Built in 1910 as a schoolhouse, the Davie School Inn is now an Inn with 11 classroom- themed suites. This one-of-a-kind Inn offers breakfast in your room, hundreds of games, puzzles and DVDs. It’s located on the edge of the Anna park and offers options for tennis, pickleball, disc golf and regular golf. Plus, it’s only two blocks to shops on Main Street, where you can rent a bike from Shawnee Hills E-bike. Anna’s Main Street offers a bakery, a coffee house and several shops, including the Annabelle Market, where you will find C’s Bees Honey and more, Shawnee Hills lavender products, home decor, jewelry, books and lots of treasurers. Enjoy dinner at the Brick House Grill, all walking distance
from the Inn.

Day 2:

Alto Pass, the Shawnee Hills Wine Trail

  • Two woman looking at the view from the deck

After breakfast at the Inn, arrange a class, tour or demo at Alto Clay Works pottery studio. Have lunch at the Peach Barn Cafe & Winery, then enjoy spectacular views from Bald Knob Cross. Take a leisurely stroll on Quetil Trail and find the steps in the stone up to Cliff View Park, then head over to Alto Vineyards, located in the foothills of the beautiful Shawnee National Forest in Alto Pass. This vineyard is Southern Illinois’ oldest, most award- winning winery and not to be missed. Step out on the back patio and enjoy seating on our upstairs vine deck, pergola, covered pavilion, or feel free to bring your own lawn chairs/blankets.


Day 3:

Cobden & Makanda

  • Woman hugging an Alpaca surrounded by sunflowers at Rolling Oak Ranch.

Start your day with 'strawberry fields forever' - or blue, black or raspberry, grab your basket and go berry picking. If you haven't filled up on berries, grab some lunch at the Iron Whisk or some homemade authentic Mexican food at the Little House of Tacos, a popular local favorite.

Visit a mother/daughter owned and operated farm, and you will get to know the alpacas that call Rolling Oak their home. While you are there you can shop locally produced products that include alpaca fiber scarfs, socks, hats and even soaps. Finish the day at StarView Vineyards with a wine slushie and light dinner.

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