It's hard for me to answer your poll. I think of "hilly" in terms of locale, not by how much actual climbing. Rides in and around Indianapolis, where I live, are all flat and are listed as such on my Bikejournal entries. There may be a minor hill or two, but you REALLY have to go out of your way to find them.

If I head about 30 to 40 miles south of Indy, it's what I consider to be hilly--of the short and steep variety. I list most of those rides as "hilly" although the total altitude gain is still pretty low.

If I head even farther south--to Kentucky or Tennessee--then I can really hit some hills, but it's rare that I get to climb an actual "mountain." I think the longest sustained climb I've done is about 3 miles. I'd really like to climb more.

Because I don't climb much, I'm liable to view any ride that has at least 4 or 5good climbs as "hilly."