Hi Lisa,
I have been to all of the restaurants you mentioned (did I already say that the other half of our trip is eating???). Is Chatham 50 miles round trip or 50 miles one way from GB? Maybe next year we can ride to your house for a day, but probably not if it's a century. I wouldn't mind taking a trip out there in the fall, either.
Well, I wouldn't think that I could do those climbs either, but I do. I always complain, but everyone just knows that I do, and then I quiet down. There's an alternate route for the "Taconic Challenge" ride, but I think the one we did in Otis was almost as long. My friend rides at a slower pace than me and she gets up everything! She's been riding for years, but I think it proves that you don't have to be a speed demon to attack the big hills. In fact, what helped me on this trip was conserving energy and slowing down.