Looking for hiking loop around 30 to 50 miles round trip

There's not a whole lot by way of long-distance backpacking routes in this region, but you're not totally out of luck. Starting in southern and central Indiana, you might take a look at the 25-mile Adventure Hiking Trail, which mostly traces sections of the Ohio and Blue rivers through Harrison-Crawford State Forest and Wyandotte Woods State Recreation Area (part of O'Bannon Woods State Park). Another longer route is the 22-mile Salamonie Trail, which follows the south side of the Salamonie Reservoir through Lost Bridge and Mount Etna state recreation areas. Hoosier National Forest also has an extensive trail system, which would allow you to knit a good loop on somewhere like the Hickory Ridge Trail (which offers 43 miles of trails). In Kentucky, take a look at the Land Between the Lakes National Recreation Area or around Daniel Boone National Forest; similarly, you can put together a longer-distance loop in somewhere like Big South Fork National River & Recreation Area across the state line in Tennessee. All that said, if you get this far east, we'd be inclined to suggest you keep going for the region's best backpacking in Great Smoky Mountains National Park!

Guess that would help. Sorry, I was on the Kentucky DNR website and thought I was addressing to that state. I am in Southern Illinois and we are looking to hike in Kentucky or Southern Indiana.

You don't say where you're based and/or where you might be hoping to backpack. Let us know that info and we'll see if we can come up with a few good ideas!