I used to love Cuttyhunk but haven't been there for a good many years.
I stopped there occasionally when I sailed from Groton (CT) or Newport (actually Jamestown) to Scituate (MA) and back. There were no moorings there then, just anchoring. I remember a particular trip with T-Birds from the Boston Fleet. I was in a raft with 3 other T-Birds when a bigger Sailboat anchored poorly upwind of us and beat feet to go ashore. The wind came up and sure enough he dragged down on us and was going to cause some damage. While others were busy fending off, I jumped aboard. Just then a big power boat came along side and threw me a line. He was going to help pull this guy off of our nest, but as soon as I grabbed the line he put pedal to the metal took off. I never had a chance to secure the line to anything, so before it came taught, I wrapped it several times around the boat's headstay and grabbed on for dear life. As you could probably guess my hand got run into the headstay and my whole palm got cut open right to the bone. Well after we got this boat re-anchored our "fleet surgeon" (a dentist), had to stitch me up, and they got me bombed on Black Russians as my anesthesia. I didn't feel a thing, but in the morning my head hurt much more than my hand. In another day however that was reversed and I was relegated to being a one handed sailor.It was still a good memory though, and Cuttyhunk was a great place to stop.Sail safelyJoe S