The good life along Illinois’ Shawnee Hills Wine Trail | Midwest Living

The good life along Illinois’ Shawnee Hills Wine Trail

Read about our fall getaway on the Shawnee Hills Wine Trail, then check out our three-day itinerary to plan your trip.


Couples can take their wine out to a deck and onto the grounds at Pomona Winery.
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The Davie School Inn in Anna.
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3-day itinerary

For more info: Southernmost Illinois Tourism Bureau. (800) 248-4373;

Day 1

Start by visiting the Shawnee Hills Wine Trail website and downloading a map of the wineries ( A GPS will help, but the route has good signage. The area stretches about 30 miles across, but because of all of the backroads, 4 miles can take 20 minutes.

Each winery provides a list of wines, from dry to sweet. Some offer food, too. The special cheesy-garlicky bread-and-oil appetizer at Blue Sky Vineyard is divine. (618) 995-9463;

The grapevine-smoked brisket sandwich at Von Jakob comes with rustic potatoes and a mixed-green salad topped with Red Oak port vinaigrette. (618) /893-4600;

A hike through Little Grand Canyon takes about two hours. (800) 699-6637;

Refuel in Anna with dinner at Brick House Grill, which tops filets with thick blue-cheese gravy. (618) 833-5367;

Antique furnishings and Southern hospitality and cooking await at Historic Bell Hill Bed and Breakfast in Cobden. (618) 697-0326;

Girlfriends love the new Alto Wine Trail Loft—a two-bedroom vacation rental in an Alto Pass historic building. (618) 698-7474;

The Davie School Inn stuns with classy decor and in-room breakfasts in a rescued Anna elementary school building. (618) 833-2377;


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