This three-day itinerary blends scenic trails, forest adventures, and maker culture
By Nicole Partis
Illinois is home to a variety of great attractions. In Southern Illinois, small towns are surrounded by wildlife-rich landscapes and striking scenery found nowhere else in the state. With opportunities for hiking, biking, boating, and even zip-lining, the region offers groups a wide range of unforgettable experiences set against an incredible natural backdrop.
Find these great attractions and more:
- Shawnee National Forest
- The Makanda Trading Company
- Shawnee Hills Wine Trail
- Pounds Hollow Lake
Looking for expert insights and fresh travel ideas? Download the latest issue of Leisure Group Travel for free and start planning your next unforgettable group adventure.
An Outdoor Illinois Day-to-Day Itinerary
Day 1: Carbondale, Makanda-Exploring Shawnee National Forest
Begin the journey in Carbondale with a gentle introduction to the landscape at Giant City State Park, part of the Shawnee National Forest. Paved paths and accessible trails make it easy for groups to enjoy the scenery without strenuous hiking, while opportunities for horseback riding, biking, fishing, and camping allow visitors to experience the park’s dramatic rock formations at their own pace.
From there, continue into the heart of Shawnee National Forest, which spans more than 280,000acres, to reach Garden of the Gods, one of Southern Illinois’ most iconic natural landmarks. A short, quarter-mile trail delivers expansive views from dramatic sandstone bluffs. Groups can spot famous rock formations like Camel Rock, Anvil Rock, and Mushroom Rock, while signs along the trail highlight the area’s geology and history. For those wanting a longer adventure, 5.5 miles of interconnecting trails allow visitors to explore the forest further, enjoy Illinois wildflowers, or see the forest’s brilliant colors.
After lunch, head to nearby Makanda, a small village known for its creative spirit and historic boardwalk. The city is perfect for browsing artisan shops, galleries, and local studios. Makanda’s blend of craftspeople, natural beauty, and old-time charm makes it a great stop for groups seeking authentic regional character. While there, groups can browse The Makanda Trading Company or Rainmaker Art Studio to discover local artisans’ work, all while enjoying views of the surrounding Shawnee woodlands.
For groups looking to add a little adrenaline, the Shawnee Bluffs Canopy Tour offers a guided zip-lining experience that glides above the forest canopy and across aerial bridges, combining adventure with sweeping views of Southern Illinois’ wooded valleys.
Return to the city for an overnight stay, and to enjoy dinner at one of Carbondale’s casual eateries or chef-driven spots highlighting local ingredients. Afterward, explore downtown, where live music venues and local theaters bring the city to life after dark.
Day 2: Pomona, Alto Pass, Cobden-Trails, Wine, And Makers
Day two highlights Southern Illinois’ signature mix of outdoor activity and indulgence. Begin near Pomona, where forested roads lead to trailheads and scenic overlooks. The popular Pomona Natural Bridge Trail offers groups an easy hike with stunning scenery, including towering sandstone formations and peaceful wooded areas.
As you make your way south through Pomona, Alto Pass, and Cobden, you’ll experience the Shawnee Hills Wine Trail, a scenic route full of vineyards, rolling hills, and local flavor. The region’s favorable weather has supported winemaking for generations, making wine tasting an easy and enjoyable way to unwind after a morning outdoors. Many wineries along the trail offer private tastings or relaxed group lunches, making it easy to tailor the experience to your group’s pace.
Pomona Winery, one of the original members of the trail, is a must‑visit stop for groups. Known for its fruit-forward wines made from local apples, peaches, berries, and grapes, the winery’s standout blueberry and strawberry wines are perfect for tasting. Covered decks and a garden picnic area allow visitors to sip and relax while taking in the peaceful forest setting.
From Pomona, continue south to Alto Vineyards in Alto Pass, the oldest winery in Southern Illinois. Founded in the 1980s, Alto Vineyards helped put the region on the map and produces a wide range of award-winning reds and whites. Groups can enjoy tastings at the outdoor vine deck with panoramic vineyard views, and weekend live music or seasonal events can add extra charm to the visit.
In the afternoon, continue further south to explore the Southern Illinois Makers’ Trail. Like the Wine Trail, this route features a collection of local artisan spots spread across the area, and part of the charm is hopping from shop to shop. Groups can explore galleries and boutiques in Cobden and Alto Pass, where artisans showcase handmade jewelry, pottery, textiles, antiques, and other local treasures. Along the way south towards Anna, groups can visit C’s Bees for local honey products or stop by fan favorites like The Chocolate Factory for sweets and ice cream.
As the day winds down, return to lodging in the Shawnee Hills area or nearby Carbondale, where the quiet of the countryside sets the tone for a restful evening.
Day 3: Du Quoin. Harrisburg-Water-Based Adventure
The final day explores the eastern side of Southern Illinois, beginning in Du Quoin, a town associated with agriculture and outdoor events. Groups can start with a leisurely morning walk or bike ride along the area’s local trails, many of which are flat and well-maintained, providing a comfortable way to stay active while enjoying the region’s rural scenery. In total, Du Quoin offers 97 miles of trails, giving groups plenty of options to explore.
From Du Quoin, travel east for about an hour to Harrisburg, a community surrounded by lakes and waterways ideal for adventure. Sahara Lake at Sahara Woods State Fish and Wildlife Area is a perfect spot for some easy outdoor fun. The 98-acre lake is surrounded by woods and gentle trails, making it ideal for a relaxed morning of kayaking, canoeing, or just hanging out by the water. Groups can also fish or take a small boat out for a leisurely spin around the lake, getting to experience Southern Illinois from the water.
Harrisburg also serves as another access point to Shawnee National Forest, giving groups a chance to experience the forest from a new perspective. Just a short drive in, you’ll find Pounds Hollow Lake, a scenic spot that’s perfect for a swim, a little fishing, or just relaxing by the water.
Finish the trip with a farewell meal in Harrisburg or Carbondale, enjoying local dishes and looking back on three days of outdoor exploration and memorable experiences.
Southern Illinois proves that adventure doesn’t have to be extreme; hiking, biking, or simply being outdoors here is a joy, with stunning forests, rolling hills, and sparkling lakes as the perfect backdrop for any group.
Looking for expert insights and fresh travel ideas? Download the latest issue of Leisure Group Travel for free and start planning your next unforgettable group adventure.
