Near Dryden, NY, is a great area known as “Hammond Hill” state forest. There are many trails criss-crossing the area and it is the area for a well known local trail race – the “Thom B” trail run (link here).
You can make nearly any distance loop out of it, although the longest would probably top out at around 12-14 miles. The trails cover lots of different ground and forest regions.
As far as total elevation is concerned, the area is certainly hilly, without being technical or severely steep. The course that the 13k race takes has about 1250 feet of gain broken up fairly evenly over the route.
Here’s a short video showing one of the more forested sections of the trail. Keep in mind this is in late April and the view(s) change greatly from winter to spring to summer to fall.
It’s a great place for a shorter run (or loops) from the Ithaca or Cortland area – if you’re in the upstate area and want to get a nice run in on a trail that is well marked and less well known compared to those near town this is a good place to go.
Hammond Hill Trail Running Near Dryden, NY via Bearded Goat Trail Running