Yeah, I started road cycling in 2001. Used to be a distance runner, but the knees and joints were getting too sore. Prefer road (don't own a MTB), because mtn seems too technical and trails tend to be too humid for my liking. Usually start riding in late March or early April, hang it up in late Nov or early Dec, run/walk/snowshoe over the winter.
I've done a fall "century" each of the past two years, to take the place of marathons I used to run. Centuries are a lot easier, but still give a feeling of accomplishment and require some training. I wear the goofy clothes because it's more effective (jerseys have pockets, tight shorts w. pads are most comfortable if you go distances).
I usually ride by myself, am slow but have stamina and do OK on hills (western/central Catskills have a lot of big ones). Group rides (clubs, bike shops) require some pack-riding skills and can get competitive. Usually do 20-75 miles at a time, favorite long weekend rides in the 60-75 mi range.
I most often ride in the general vicinity of the Pepacton Reservoir. From Kingston, you should be able to find some good routes toward the Ashokan Reservoir and Rondout Valley.