I'm with @
Biker395. I love hills and hate wind. Unfortunately, my 13-mile commute is almost all flat and extremely windy. I get a strong headwind in the morning, and then normally, the wind turns around to give me a mild headwind in the evening.
It's pretty hilly near our weekend house, and I'm looking for hills that will challenge me. My limit is not my physical ability but my distance from big hills. I'll find some routes west into the Catskill mountains. I see they're pretty big compared with our hills, and I'm sure a few will be challenges.
For what it's worth, I'm 5'9" tall and 155 lbs, i.e. fairly light.