The Ultimate Southern Illinois Adventure Weekend Itinerary: Hiking, Mountain Biking, Ziplining & Wine

Who says you have to choose between outdoor adventure and relaxing with a great glass of wine?

When you stay at Shawnee Hills Hideaway, you're just minutes from some of southern Illinois' most exciting outdoor experiences. Spend your days soaring through the treetops, hiking among towering sandstone bluffs, tackling world-class mountain bike trails, and exploring charming small towns. Then return to your peaceful suite, uncork a bottle of local wine, and relax on your private deck surrounded by nature. Needing some inspiration? Check out this two-day adventure itinerary.

Soar through the treetops at Shawnee Bluffs Canopy Tour, one of southern Illinois' premier outdoor adventures. This thrilling zip-line experience offers breathtaking forest views, suspension bridges, and an unforgettable way to experience the beauty of the Shawnee National Forest.

Day One: Zip Through the Trees & Hike the Streets of Giants

Start with Breakfast in Cobden

Fuel up for an active day at The Iron Whisk. Their ever-changing brunch menu features fresh, seasonal ingredients, hearty breakfast favorites, and their famous Dutch Babies. It's the perfect way to start an unforgettable weekend.

Morning Adventure: Shawnee Bluffs Canopy Tour

Just minutes from your suite, experience one of the Midwest's most unique adventures at Shawnee Bluffs Canopy Tour. Spend three unforgettable hours soaring through the forest canopy on eight thrilling ziplines connected by aerial suspension bridges and scenic woodland hikes. The course stretches across 83 wooded acres deep within the Shawnee National Forest, giving you incredible views you simply can't experience from the ground. Advance reservations are recommended.

Afternoon: Explore Giant City State Park

After your zipline adventure, head to Giant City State Park. If it's your first visit, don't miss:

• Giant City Nature Trail – The park's signature trail featuring massive sandstone walls that create the famous "streets" of Giant City.

• Trillium Trail – A peaceful woodland hike with beautiful scenery, wildflowers, and excellent opportunities for spotting wildlife.

Looking for an extra challenge? Giant City is also one of southern Illinois' premier destinations for rock climbing and rappelling, offering designated climbing areas for experienced climbers.

After a day of exploring Southern Illinois, there's no better reward than unwinding with an award-winning bottle of wine at Wichmann Vineyard. Located just two miles from Shawnee Hills Hideaway, it's the perfect place to relax, savor local flavors, and toast to your next adventure.

Late Afternoon: Wine Down

Adventure deserves a reward. Head over to Wichmann Vineyard and enjoy a relaxing wine tasting while overlooking the vineyards. There's simply no better way to celebrate a day spent outdoors than with an award-winning Shawnee Hills wine.

Dinner Tradition

Finish your evening with southern Illinois' most famous meal at Giant City Lodge.  Their legendary family-style fried chicken dinner has become a tradition for generations of visitors, and after a full day of adventure, you've definitely earned it.

Start your second day of adventure with a hearty breakfast at Harbaugh's Café in Carbondale. From homemade favorites to generous portions, it's the perfect place to fuel up before hitting the Touch of Nature mountain bike trails and exploring more of southern Illinois.

Day Two: Ride, Relax & Explore

Breakfast at a Local Favorite

Begin your morning at Harbaugh's Cafe in Carbondale. Known for generous breakfasts and friendly service, it's a favorite stop for both locals and visitors before heading out for the day.

Morning Ride: Touch of Nature Mountain Bike Trails

Ready for another adventure?  The Touch of Nature Outdoor Education Center trail system offers some of the best mountain biking in southern Illinois. Whether you're a beginner looking for flowing single track or an experienced rider seeking technical terrain, you'll find miles of forest trails winding through beautiful scenery just minutes from Shawnee Hills Hideaway.

Refresh at the Hideaway

One of the biggest advantages of staying at Shawnee Hills Hideaway is location.

After your morning ride, you're only minutes away from your comfortable suite. Take a hot shower, relax for a bit, and get cleaned up before heading back out for an afternoon of exploring.

Few places capture the beauty of southern Illinois quite like Blue Sky Vineyard. Surrounded by rolling vineyards and breathtaking views, it's the perfect place to sip estate-grown, award-winning wines, enjoy live music on the weekends, and experience the warm hospitality that makes the Shawnee Hills Wine Trail and southern Illinois an unforgettable destination.

Lunch, Live Music & Local Wine

Next stop: Blue Sky Vineyard. Enjoy lunch paired with a handcrafted glass of wine while taking in the beautiful Tuscan-inspired setting surrounded by acres of vineyard. On Saturdays and Sundays, live music fills the patio from 2:00–5:00 PM, making it one of the most relaxing places to spend an afternoon.

Stroll Through Makanda

No trip to southern Illinois is complete without wandering the historic Makanda Boardwalk. Known by many as "America's Little Hippie Town," Makanda is filled with charming shops, local artists, handcrafted gifts, galleries, and unique treasures you won't find anywhere else. Take your time, browse the boutiques, grab a sweet treat, and soak in the laid-back atmosphere that has made Makanda a favorite stop for decades.

One Last Stop Before Heading Home

Before calling it a weekend, swing through Carbondale and pick up a famous pizza from Quatro's Deep Pan Pizza.  Bring it back to Shawnee Hills Hideaway, uncork the bottle of wine you picked up during your travels, and enjoy dinner on your private deck as the sun sets through the trees.

Sometimes the best restaurant in southern Illinois is your own peaceful patio.

Stay Close to Everything

One of the best parts about staying at Shawnee Hills Hideaway is that you're never far from your next adventure. Within just a few minutes, you can be ziplining through the forest, hiking among towering sandstone bluffs, mountain biking scenic singletrack, exploring local wineries, discovering artisan shops, or enjoying some of the region's best restaurants.

Adventure all day.  Relax all evening.  That's what a southern Illinois getaway should be.

Book your stay at Shawnee Hills Hideaway and discover why it's the perfect base-camp for your next adventure. Book Your Adventure