On Monday, September 23, the northwest wind was already in gear well before dawn, and I along with it. By 0545 the anchor was up, with a tiny bit of light coming up in the east, and lots of moonlight. At a little after six I was passing Gayle and Bruce’s house, and shortly after that, with the tide carrying the boat along, we were out of the harbor and off. Leaving, as Sarah Orne Jewett put it so well, the country of the pointed firs. And the beautiful rocks, and the islands.

At least this year I knew what I was up to, and got to say goodbye! Last year, sailing through the night was a plan made in the evening, when there wasn’t enough wind to get in to a Casco Bay harbor before dark anyway. But I didn’t think I’d get so far! That time, the wind came up about 10 PM, and when the sun rose in the morning I was off of Kennebunkport. By that afternoon I was anchored in Portsmouth, NH. It was a bit of a shock, with no preparation, that separation from the islands and the northern trees.

This year I knew what was possible. A substantial northerly wind was forecast, and with a plan in mind, I was setting out for Massachusetts. There were several potential destinations, depending on what the wind actually did: Cape Ann (Gloucester, etc.), Provincetown (on the outer end of Cape Cod) or, as a remote possibility, going completely around the outside of Cape Cod all in one shot.

Going around the outside of Cape Cod all in one go was ruled out pretty early (yes Bill, I heard that sigh of relief) – the straight-line route would have involved being quite far offshore, and the wind forecasts were a bit high, pushing the edges of my comfort zone at 15 to 25 knots. Having the trickiest part at the end of the long ride, rather than at the beginning, didn’t look so great either. Further, once you are through the delicate business of getting into Nantucket sound through Pollack rip, you then have to sail through Nantucket sound! Which is long, full of shoals, and pretty busy with traffic. No naps once you’re in there…

Provincetown was a real possibility, and in hindsight, it would have been a lot easier. Even though it was considerably farther than Cape Ann, it would have been a broad reach through the biggest waves in the first 24 hours, and later when the wind went to the west it would still have been possible to maintain the desired heading.

At the time, it felt like that course would have been a bit much, as far as distance from shore in the feisty weather. And it would have left me still needing to either sail back to Cape Ann, or to do something about getting past Cape Cod, in order to get home. Added to that, my brother, sister-in-law and nieces are right by Cape Ann. I was going to be sad if, all the way in Provincetown, it somehow didn’t work to get back to see them.

So Cape Ann it was. Sailing through the night was a little wild. The seas weren’t all that high, as those things go, but they were very steep and short. The boat was fine, and I was perfectly alright, but it wasn’t the most fun sailing in the world. Every now and then there would be a loud, jarring smack, as an especially big wave hit just right, on the side of the boat. I could’ve done without that!

On the upside, it was very fast. By nine in the morning on Tuesday, at 20 miles out from Cape Ann I could see its higher hills. A little after that the wind slacked off, and then went more west. In combination with the “slop and bobble,” that was about it for nice, efficient progress. I had the idea that I wanted to go to Lobster Cove, inside the north end of the Annisquam River. As the wind shifted, that destination, and everywhere else on Cape Ann, involved tacking. Oh well! The first 10 miles weren’t so bad, sorting out by the end of the morning. The last 10 miles took forever.

By six o’clock that evening I had resigned myself to the idea that I would be out for the night. Earlier I had resigned myself to the idea that I wasn’t getting to Lobster Cove, or anywhere else if I kept trying for that destination, as we were, basically, endlessly tacking in place. The boat wanted to sail off to the east of the lighthouses on Thatcher Island, and I had finally given up on trying for shore, and said okay. Heading more broadly on our starboard tack, we actually started going somewhere.

After a couple hours of progress, leaving Cape Ann to the west off the starboard beam, the wind eventually died back to nothing. The sun was getting lower, the sea was glassy, and the boat was making no progress past the bubbles in the water. I got all the night things in order, and settled down for a rest until whatever was going to happen next. The boat was well in sight of the two lighthouses, about 5 miles southeast of Rockport Harbor.

Amazingly, that next thing started in about 15 minutes. A surprising amount of water noise for such a calm time got me looking out the windows. Ripples! Not just the tiny ones that usually start some gradual change, these were significant ripples. I hopped up – funny how a breeze after a long wait is so energizing, even when you are knockout tired – and next thing you know we were really sailing. Within 10 minutes there were whitecaps and I was reefing the sails. All of this with a wind out of the northeast, and some clouds, but no rain in sight. It wasn’t a typical looking front, and no big front was expected, but it did look like it might not last. Lobster Cove came to mind – now a beam reach to get around the corner, and then downwind – but it was a good 10 miles away, and it would be dark in about an hour. And there was that this wind could be a short-term event.

I consoled myself that Rockport, at about 5 miles, was sort of on the way to Lobster Cove, so if things looked just right I could change my mind and continue on. But realistically, the end of the Annisquam River is a tricky entrance through a narrow slot in a bar, and I’m not familiar enough with it to feel good about doing that in the dark, especially with the moon not coming up until much later. By the time I was in the outer part of Rockport Harbor it was getting dark and I was taking reefs out of the sails, and by the time I was in the inner harbor it was night. I had hailed the harbormaster on the radio, and he said I could come in to a float at the edge of the mooring field. There’s no anchoring in Rockport, because it’s so tight.

Last year, sailing with Dave and Anke, we came into this very harbor, also as it was getting entirely dark. That time the harbormaster had us come into the tiny, completely enclosed basin inside the end of the inner harbor, where we tied up to a floating dock against a high stone wall. It was heavenly, and I was so hoping for an invitation to that spot, but was glad to have any spot at all, and didn’t want to push things by asking. Though honestly, I was ready to cry when the fellow on the radio did not suggest coming in there. Rockport Harbor rolls a lot, especially in an easterly wind.

Sails furled and the motor on (this is why it’s on the boat!), I was approaching the float that had been described on the radio. There was a man on the public dock with a flashlight looking toward me – the harbormaster himself, with invitation to that inner dock! I could’ve cried again. By 8 PM the boat was snug on its docklines, and by nine I was sound asleep.


Today is a rest day – much needed. I do get naps during those long overnights. The AIS is there to tell me if there are ships, a kitchen timer is set for two hours, though I usually wake up after one to check on things, and the advantage of sailing during a small craft advisory is that the small traffic is all in port. Before naps I plot the boat’s position and think in terms of the closest thing that I could run into, and the fastest time that the boat could physically get there at highest speed and greatest possible current. Then the timer gets set for no more than half that fastest time. I do like going a good bit off the shore, just to have loads of extra space with nothing to worry about like islands and rocks.

On this overnight I actually got a fair amount of sleep – adding up all the naps, something around six hours. But that rough weather was exhausting, and I was much more tired than after the entire northbound run around Cape Cod. Now it’s fantastic to be in such a snug spot, and to be here for a second night, thinking of when I was at this dock a year ago with Anke and Dave.

And Massachusetts! I’ve gone far enough this year to actually be quite happy to be going home. And I was daunted by the long sailing to be done to get back south. Now it’s in the books! It’s still possible that I might do something to get to the other side of Cape Cod, so as to visit in Narragansett Bay and come home to the Connecticut River. But it’s also possible that this could be enough for now, with the chilly weather coming so fast. There are two or three good boat ramp possibilities in this area, with about a two-hour drive from here to Holyoke. There is visiting this weekend, and perhaps some more visiting after that, and there are beautiful estuaries on the north side of Cape Ann that I would love to explore. So we’ll see what happens…