For day hikes, Pine hills is a neat place (adjacent to Shades State Park). I've been there once, but I stopped when they group got to the place they call "devil's backbone" because I didn't think it would be safe for me.
I don't think it would meet abnk needs, though, as it probably wouldn't challenge him or someone similarly fit unless you were carrying a substantial load.
The Nature Conservancy in Indiana - Pine Hills
Hoosier National and the Charles C. Deam wilderness area are where you want to go. There are plenty of 1 - 15 mile loops.
Deam Wilderness
on Charles Deam and Hoosier National Forest in general. I've logged countless days and miles in the Hoosier National, as well as Shades, Turkey Run, Pioneer Mothers Forest, Hemlock Cliffs, German Ridge, Knobstone Trail, etc. There are miles of trails in the Deam wilderness area alone. Also a great place just outside IN is Red River Gorge, south of Lexington KY (about 4 hrs south of Indy). Cant leave out Shawnee National Forest in southern IL. either. I would be more than willing to share maps and trail info over beers or between shooting, with anyone interested...Hoosier National and the Charles C. Deam wilderness area are where you want to go. There are plenty of 1 - 15 mile loops.
Deam Wilderness
But, I'm biased to Shades as I used to work there.
PLUS, there's a SHOOTING RANGE just outside the park entrance. $3/day to shoot...
-J-
Also a great place just outside IN is Red River Gorge, south of Lexington KY (about 4 hrs south of Indy).