I was just leaving shore rowing back to my boat when at the end of the dock, to both our surprise, I saw them approaching right into my path. I quickly turned around to get out of the way. Their mooring is in a small cove with little space to maneuver, with a lobster shack next to it.

I knew why they were so close to me and the dock. She (at the helm) needed all the space between the dock and their mooring, to get downwind - far enough - to turn up into the mooring, and lose their momentum.

This is a local boat so they know their water well.

Both looked quietly confident but also very engaged,mentally, in what they were doing. They had sailed into Pulpit Harbor on a strong South wind, which is tricky. Their jib was now furled and they were moving pretty well, under main and mizzen.

At the moment she chose - from a broad reach - using almost all the water there was, they rounded up toward the mooring. The moment of truth: Pretty heavy boat, a B40, it goes on, and on, for a long time.

She knows the boat. While he had his hands full as a warp had crossed their mooring, there was no drama or problem. The bow stalled and waited at the mooring, until, they were hooked. Down came the main.

Challenging yes, but it 'appear' stressful, for them. Still, it wasn't as easy as furling sail outside and powering in.

Why did they do it?

Here's my take. I think there is real satisfaction in knowing your skills, your boat, your water, your sailing. Maybe a better way to say it is, it's a joy to be at the top of your game, in anything you do. For some, the extra challenge(like sailing onto a mooring), is something they look for.

The incident you list sounds like the sailor was wrong on all accounts. Way too crowded(in my mind) and he hadn't thought through a predicatable 'what if?'