check out the Knobstone trail, a 50 plus hiking trail in southern Indiana
goes like this, Day 1: Spurgeon Hollow JWSF south to Elk Creek, SFWA, 13-15miles
Day 2: Elk Creek SFWA south to Leota trailhead, 7miles
Day 3: Leota Trailhead south to New Chapel trailhead, 9 miles
Day 4: New Chapel Trailhead south to Jackson Road Trailhead, 13 miles
day 5: Jackson Road Trailhead south to Deam Lake SRA, 5 miles
take your pick on where to start.
For southern Illinos check out the river to river trail in the Shawnee National Forest