Winter in the Shawnee Hills is quiet. The leaves are gone, so you can see the bluffs. The trails are empty, so you can hear the creek. And the wineries are warm, with a fire going and a glass waiting. It is the best-kept season in Southern Illinois, and it fits perfectly into one weekend.

Here is how we would spend it, from a cabin with a private hot tub at The Hills in Cobden.

Cabin at The Hills in Cobden, Illinois, among bare winter trees

Friday Night: Arrive, Soak, Slow Down

Pull in, unload, and leave the week in the car. The cabin is warm. The kitchen is stocked. Out on the deck, the hot tub is already steaming in the cold air.

The firepit is ready for an evening of good conversation and laughter. Cook something simple. Then sink into the water and look up. Winter skies here are dark and clear, and the stars come out early. That is the whole plan for tonight. You earned it.

Private hot tub on a cabin deck at The Hills in winter, Southern Illinois

Saturday Morning: Giant City State Park

After coffee, drive over to Giant City State Park near Makanda. This 4,000-acre park is a National Natural Landmark, and winter is when it shows off. With the trees bare, the giant sandstone walls stand out like city blocks. That is where the name comes from.

Start with the Giant City Nature Trail. It is about one mile and easy, and it winds through huge rocks. Want more? Take the Trillium Trail, about two miles of rugged path along sandstone bluffs.

Stone steps winding between tall mossy sandstone walls on the Giant City Nature Trail in Southern Illinois

Go on the Gnome Roam (December 1 – February 28)

Every winter, little gnomes hide on seven Giant City trails. Find all seven, snap a photo with each one, and show your photos at the Giant City Visitor Center to earn a gnome patch. Most of the trails are short, so it is a fun hunt for kids and grown-ups alike. Trails are open dawn to dusk. The Visitor Center is open most days from 8 a.m. to 3:30 p.m., so plan to claim your patch before it closes.

For lunch, head back toward Cobden and warm up at The Iron Whisk, a local favorite just minutes from your cabin. Hours can change in winter, so call ahead before you go.

Saturday Afternoon: The Shawnee Hills Wine Trail

The Hills sits right on the Shawnee Hills Wine Trail, so the afternoon is easy. The trail has 11 wineries, and several are just minutes from your cabin in Cobden, including StarView Vineyards, Owl Creek Vineyard and Wichmann Vineyard. Alto Vineyards and Von Jakob Winery & Brewery are a short drive away in Alto Pass.

Our tip: start at Feather Hills Vineyard, our neighboring winery, just steps from your cabin. No driving, no rush.

Good to know: Wineries keep shorter hours in winter, and some close early or on certain weekdays. Check each winery’s hours before you go, and always pick a driver.

White, rosé and red wine glasses on a deck rail overlooking a pond on the Shawnee Hills Wine Trail

Back at the cabin, it is hot tub time again. Cold air, warm water, and storytelling time.

What to Pack for Winter in Southern Illinois

  • Layers, a warm hat and gloves
  • Waterproof hiking boots (trails get muddy and icy)
  • Binoculars for eagle watching
  • A swimsuit and robe for the hot tub
  • Groceries for the full kitchen

Your Winter Basecamp

Every cabin at The Hills has a private hot tub, a firepit, a fully stocked kitchen and fast Wi-Fi. Cabins sleep 4 to 8, so it works for a couple’s escape or a weekend with your crew. You are minutes from the wine trail and a short drive from Giant City and the Shawnee National Forest.

Hot tub cabin with a wraparound deck at The Hills Cabins in Cobden, Illinois

Winter Weekend FAQ

Is Southern Illinois worth visiting in winter?

Yes. Winter brings quiet trails, clear views of the sandstone bluffs, bald eagles from December through March, and cozy tasting rooms on the Shawnee Hills Wine Trail.

Are the Shawnee Hills Wine Trail wineries open in winter?

Many are, but with shorter winter hours. Check each winery’s hours before your visit.

When is the Gnome Roam at Giant City State Park?

December 1 through February 28. Find the gnomes on seven trails and claim a patch in person at the Giant City Visitor Center.

Where can I see bald eagles in Southern Illinois?

The Union County Refuge near Jonesboro is a popular spot. Go at dawn in January or February for the best chance. Call ahead for updates on bald eagle sightings.

Where should I stay on the Shawnee Hills Wine Trail?

The Hills Cabins + Campground in Cobden sits right on the wine trail, steps from Feather Hills Vineyard, with private hot tub cabins that sleep 4 to 8.

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