How To Spend A Weekend In Illinois

Why isn’t anyone talking about the Southern Illinois Wine Trail?

This thought rang through my head as I drove through vast corn fields that go as far as the eye could see. I could also see long stretches of vineyards, apple trees, sunflower fields, and peach farms scattered throughout. I drove down the quiet streets of the Shawnee Hills Wine Trail with my windows down, hearing nothing but strong gusts of wind and my road trip tunes playing aloud. With minimal noise or crowds, it felt like ultimate relaxation, and it was exactly what I needed.

I already had a pretty good impression of Illinois from a previous trip to Chicago, but I didn’t know what to expect from Southern Illinois. Despite being less than a 3-hour flight from Houston and a 1-hour flight from Chicago, I hadn’t heard much about this part of the state.

Fortunately, Enjoy Illinois invited me to explore the Shawnee Wine Trail and discover all that Southern Illinois had to offer. The Shawnee Hills Wine Trail is 40-miles long and consists of eleven wineries along Highway 127 and 51. Most visit for the wineries but the area offers much more for those looking to explore further. From U-pick apple and peach farms to pumpkin patches, sunflower fields and more. Then there’s the sprawling forests that cover the region, like Shawnee National Forest, which spans 289,000 acres. Oh and we’re just getting started. This article will guide you on a journey that will showcase the best of Southern Illinois and the Shawnee Hills for your future roadtrip. Ready? Let’s get into it!

All About the Shawnee Hills Wine Trail in Southern Illinois

There are 11 wineries in the Shawnee Hills:

Alto Vineyards

Blue Sky Vineyard

Feather Hills Vineyard & Winery

Hickory Ridge Vineyard

Honker Hill Winery

Kite Hill Vineyards

Owl Creek Vineyard

Peachbarn Winery & Café

Pomona Winery

StarView Vineyards

Von Jakob Winery & Brewery

When to Visit the Shawnee Hills Wine Trail in Southern Illinois:

I visited during the month of September when the weather was quite literally perfect—mid-70s to mid-80s. We often felt like we had the whole place to ourselves, which was sublime. While the summer months are certainly warmer, the weather is still incredible at a high of 90 degrees. In Summer you’ll experience more crowds, but this also means businesses will have longer hours and there will be more events throughout the area. Surprisingly, the winters are relatively mild with an average temperature around 50 degrees. So why visit in the winter? Well, you can receive discounts with the Shawnee Hills Wine Trail Passport Program. This program is only $20 and you’ll save with winter specials on food, wine, and more!

While I couldn’t have been more pleased with the perfectly warm weather we experienced at the end of September, I would have loved to see the changing of the leaves in October or the sunflowers in full bloom during early Spring. Plan accordingly based on your interests!

How to Get Around the Shawnee Hills Wine Trail in Southern Illinois:

I rented a car to explore the region, which gave me the freedom to make stops wherever my heart desired. Alternatively, you can book a seat on the Shawnee Shuttle, which will include pick-up/drop-off from your accommodation and a trip coordinator to help you map out the ultimate itinerary.

Where to Stay on the Shawnee Hills Wine Trail in Southern Illinois

While there aren’t a huge number of major hotel chains on the Shawnee Hills Wine Trail, there are certainly some unique bed and breakfast options.

Davie School Inn

We stayed in a former public school! Yes, you heard that right! Davie School Inn is a unique B&B that was once a public school in Anna, Illinois. While the building has been refurbished into a modern hotel, there are still visible remnants of the 1900s school in the gymnasium, classrooms, and other areas of the building. The owners, Tammy & Lyle, are extremely welcoming and make a mean breakfast. You’ll have a homemade spread delivered to your room each morning and it’s just as amazing as it sounds. The cinnamon rolls are to die for, and I don’t say this lightly—we both agreed that they’re the best we’ve ever had. Don’t believe me? Go and see… or taste for yourself. Davie School Inn is full of quirks and it’s clear why it’s rated five stars on Google.

Historic Hull House Inn

As you drive further down the trail towards Murphysboro, you’ll find the charming Historic Hull House Inn. This Victorian-era inn was built in 1887 and was once the home of William H. Hull. There are three different quarters onsite and the property is set just outside of Shawnee National Forest. The Inn is on the National Register of Historic Places and I was in awe of the historic architecture. It felt pretty amazing to be staying in a piece of history. I don’t get that experience often in Texas.

Where to Drink on the Shawnee Hills Wine Trail in Southern Illinois

You’ll have plenty of wineries to fill your itinerary as you venture through the region (see above), but here are my recommendations:

Hickory Ridge Vineyard – This winery was the highlight of our trip! It’s homey and quaint, while leaving a lasting impression. With the rolling vineyards and vine-covered patio, you’ll feel right at home. The stunning scenery is accompanied by a superb selection of dry wines. I ordered a flight to sample the best of the best and I was not disappointed. “Sip” back, relax, and enjoy the views!

Alto Vineyards – This is one of the more well-known and frequently visited wineries on the wine trail, and that’s for good reason. It is the oldest and has won the most awards of them all. The server recommended their award-winning Chambourcin, which is a signature red wine in the region. This was one of the many wines I tasted in my sampler and let’s just say I was more than pleased. Oh, and I may be stating the obvious here, but you absolutely must order a charcuterie board alongside your wine flight.

Blue Sky Vineyard – Tuscany or Southern Illinois? You’ll definitely feel like you’re in Italy at the beautiful Blue Sky Vineyard. You can even stay in a suite at the vineyard if a tasting just isn’t enough. Who else could say that they woke up to vineyard views this week? Because I certainly can!

Where to Play on the Shawnee Hills Wine Trail in Southern Illinois

Explore Shawnee National Forest 

You’ll have the opportunity to wander through nearly 300,000 acres of land at this national forest.

  • My personal favorite stop? The Garden of The Gods. A local told me that this was an absolute must see, so we had to take his word for it. It lived up to the hype, and I must admit that it exceeded my expectations for natural wonders in Southern Illinois! If you don’t do anything else (aside from wine sipping), visit the Garden of the Gods.

  • Another must-see? Giant City State Park. You’ll hike through greenery and slither through bluffs during your adventure. You can explore by foot or even horseback!

Other places to visit inside the Shawnee National Forest?

Pomona Natural Bridge

Little Grand Canyon

Jackson Falls

Burden Falls

Sand Cave

Get High at Shawnee Bluffs Canopy Tour

If you’re in need of an adrenaline rush, look no further than Shawnee Bluffs Canopy Tour. You’ll conquer eight zip lines across 83 wooded acres. The guides will provide safety instructions, and they’ll teach you about the ecology of the area. As someone who is always chasing the next thrill, this was exactly what I needed.

Head To The Orchards 

Go apple and peach tasting at Rendleman Orchards and Flamm Orchards. The peaches at Rendleman Orchards give Georgia peaches a run for their money. Don’t leave without tasting the peach cobbler! Flamm Orchards will serve you up the best apple pie of your life. We even brought a bag of apples back on the flight! If that doesn’t tell you how amazing their product is, well, then I’m not sure how else to convince you.

Where To Eat On The Shawnee Hills Trail in Southern Illinois

You can certainly eat at the wineries and orchards along the trail, but here are a few food recommendations if you want to switch things up:

17th Street BarbecueThis BBQ joint is said to have the best ribs in the U.S., but the sides are highly underrated. The fried pickles and the baked beans are the best I’ve ever had, and this is coming from a Texan, where BBQ is a staple.

Faye Coffee Shop Faye offers light bites and quality coffee inside a refurbished century-old building. While the building may be historic, you’d never know with its sleek interior design. It’s right across from Historic Hull House Inn in Murphysboro (previously mentioned).

Grafton Winery and BrewhausThis is a bit further out in Grafton, but it’s a great stop for the beer lovers who might need a break from wine. Enjoy some German bites and craft beer as you soak up the Southern Illinois vibes on the restaurant rooftop. Okay, okay, if you haven’t had enough wine, you can order wine that is sourced from their winery too. Live music is often offered on weekends, so be sure to check their Facebook page to keep an eye on events.

I wish I could say “That’s All Folks!”, but there’s so much to do with so little time. As I always say, I’ll have to return for more. Ideally, I’d return when the sunflower fields are in full bloom and the peaches are ripe for pickin’! Another trip, another U.S. gem that has taken me by surprise. You can’t go wrong with the perfect balance of relaxation and exploration. Whether you’re passing through on a roadtrip or planning a dedicated stay along the Shawnee Hills Wine Trail, be sure to make the most of your trip with this guide. “‘Wine’ not?” You won’t be disappointed.

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Hey, I'm Ciara. I’m a global citizen and lover of travel. Want to know more? 

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