I'm going to have to take some liberties with "ten miles or so", because a loop hike of ten miles is virtually certain to involve roadwalking on Platte Clove Road/CR16. But there are a few possibilities that are slightly shorter that offer possible side trips and might fit your desires nicely.
1. One possibility would be to come up Devil's Path from either Prediger Road or the Platte Clove Preserve, traverse Indian Head, optionally make a side trip to the summits of Twin, and then return to your car by way of Jimmy Dolan Notch. That would visit Sherman's Lookout and several good views from the summit ridge of Indian Head. (Note that there is no view from the summit itself.) It would also take in Plattekill Falls if you were to start from the preserve.
http://www.catskillmountaineer.com/IH-indianhead.html shows the route, although I'd prefer doing it clockwise rather than counterclockwise. I feel safer scrambling up than down.
2. Or park at Roaring Kill, climb Sugarloaf by way of Mink Hollow and come back down Pecoy Notch. That would visit Dibble's Quarry, skirt a pretty beaver pond, get some more nice views from the summit ridge, and offer possible side trips to Twin (including the cave on the west side) or to Plateau.
http://www.catskillmountaineer.com/IH-sugarloaf.html
Each of these hikes is about seven miles without the optional side trips. They don't require technical climbing unless they're icy, but they are extremely challenging. If you're not used to hiking steep grades on sandstone and shale, take it easy at first. The sedimentary rock is treacherous compared with the granite up North.
3, If you're not in the mood for a lot of scrambling, you can get a much more gradual out-n-back with side trips by parking at the Plattekill Preserve, and hiking the Overlook Turnpike as far as the ruins of the Overlook Mountain House. Include side trips to the Codfish Point quarry, the Overlook fire tower, and Echo Lake, and you have about your ten miles.
http://www.catskillmountaineer.com/IH-overlook.html This hike is one of my favorite short backpacks, with a stay at Echo Lake. Do the fire tower and Codfish Point on the outbound leg, and Echo Lake on the return, or vice versa, and it'll feel almost as if it were a loop. Besides, it's hard to get tired of views like this:
View from the Overlook Mtn ledge by
ke9tv, on Flickr
Don't miss the side trip to Plattekill Falls!
http://dftscript.blogspot.com/2012/04/t ... -1213.html
If you like, you can also follow an unblazed woods road west from the Codfish Point junction to a second quarry, and even bushwhack south to the summit of Plattekill Mountain; there's also a pretty overlook above Echo Lake just beyond.
http://www.catskillmountaineer.com/IH-plattekill.html (Don't attempt the summit without a topo map and good orienteering skills!) The Plattekill Mountain excursion would be a better trip on snowshoes or skis; the views aren't that great when the leaves are on the trees.
All of these hikes are on NY/NJ Trail Conference map #141.