century ride/HIM

OK--my tri season is coming to an end and I am thinking about next year. I will be doing NYC marathon on Nov. 1 and I completed my first Oly distance. My "big goals" for next year will be a century ride and a HIM!! I would love recommendations for either of these goals. I am willing to travel as long as it is a reasonable distance by car. I would like a HIM that is friendly for first timers. I was thinking Jerseyman, but it is too early in the season. Ideally, I would like it to be toward the end of the season. Even if it is not a HIM--a "half Lite" would be fine--I think that is how they refer to distances between an Oly and half. As for the century--I just want a pretty ride that is not a real killer.