I am dropping my two sons off at college in Iowa in late August. We are flying into Chicago and renting a car from there. I am tempted to drive back to Boston and squeeze in 2-3 days of backpacking along the way if there is some good options. My route can vary, but going from Cleveland towards central PA looks like it might have potential. I can also drive a northerly route that goes thru Syracuse and the Finger Lakes region. I know there would be good options in the Adirondacks, but these are reachable from Boston in a day, whereas Ohio / PA and Central NY are a stretch, so I would like to take advantage of this trip to hit someplace I might not otherwise make the effort to get to from Boston. That said, if the Adirondacks have the best options I am open to that area as well.
I am looking for any suggestions, but my criteria has some limits:
1. I usually consider 8-12 miles a good days hike. Could go a little longer depending on terrain.
2. Not much for epic climbs, although epic views are high on my list.
3. Prefer a loop hike or out and back for logistical reasons
Thanks in advance for your recommendations.

