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A vineyard with a house

Zip, Skip and Sip Your Way Along The Shawnee Hills Wine Trail

From Local Experts

3 Days 110 Miles


Alto Pass, Anna, Cobden, Makanda, Murphysboro

Explore the Shawnee Wine Trail in Southern Illinois

From the local experts at the Southernmost Illinois Tourism Bureau

The Shawnee Hills Region in Southernmost Illinois is home to a wide array of unique experiences. Enjoy the breeze zipping through the trees, skip your way through beautiful flower fields and along trails in the woods. Finish up your afternoons with award-winning wines from the Shawnee Hills Wine Trail or a craft brew. You’re sure to have created memories that will be treasured long after the last sip.

Day 1:


  • Meat on the grill

Murphysboro is Illinois’ BBQ capital. BBQ aficionados have long known the trip here is more than worth it. The small town is perhaps the only in the country with two Barbecue Hall of Famers. In addition to the BBQ history, experience a booming craft beer movement that is vibrant and exciting. Explore a variety of shops and the General John A. Logan Museum.

Grab dinner at Pat’s BBQ before checking in to Hull House Inn. 

Day 2:

Alto Pass, Anna, Pomona, Harrisburg

  • Bike with flowers

Travel south on the rolling hills of Hwy. 127, along the Shawnee Hills Wine Trail. Enjoy the distinctive character of several wineries as you explore the scenery of the Shawnee National Forest. Go on a short hike at the Pomona Natural Bridge, or a more in depth adventure at the Little Grand Canyon area. Skip through the zinnia, sunflowers and pumpkin patch at Rendleman Orchards. Explore the village of Alto Pass, then take the scenic drive up Bald Knob Mountain for spectacular views of the forest valley.

Visit Alto Vineyards Winery & Tasting Room or Von Jakob Vineyard & Brewery before dinner at Brick House. Stay overnight at Davie School Inn.

Day 3:

Cobden, Makanda

  • Two people drinking wine

The small village of Cobden offers a local history museum (open on the weekends), shops and diners. Old Hwy. 51 travels through the countryside, and crosses over to Makanda Road, which leads into the village of Makanda – the gateway into Giant City State Park. While in Makanda, see if you can find the "secret garden". 

Giant City State Park was named for the unique impressions made by its massive sandstone structures and is home of the “Giant City Streets” - where huge bluffs of sandstone formed 12,000 years ago. The Visitor Center provides interpretive displays and area information. Don’t forget to check out the Lodge, which offers dining and cabin options.

Unwind at Owl Creek Vineyard and Winery, Blue Sky Vineyard or Flamm Orchards Fruits and Cream before turning in at Boars Nest Cabins.

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