A fall cruise in the Northeast is a risky proposition. Any time you venture into these waters after October 1, you have to weigh the allure of solitude and breathtaking beauty against the possibility that the clear and warm of today will collapse into the clouds and chill of tomorrow. Most boaters just don’t bother and haul out as soon after Labor Day as practical. But for the hearty and daring, the gamble can be rewarding. If you manage to bracket a couple of cold fronts and if it’s one of those special New England autumns, you’ll get a cruise you’ll never forget.
Besides luck, you’ll need the right boat and local knowledge. One fall I had both. Thanks to Marquis Yachts and Bosun’s Marine in Quincy, Massachusetts, I had use of a Marquis 420 SB, complete with the all-important lower station for those times when sun and serenity turn to cold and chop.
Marquis also supplied local knowledge in the form of Capt. Rick Kilborn, a comprehensive boater trainer. He knew the area intimately, as did photographer Jim Raycroft—a good thing since I didn’t; I’d always skirted it on my way up to Maine. Rounding out our crew was Audrey Felske, Jim’s assistant and another experienced boater.
By the time we had finished fueling our 420 and recommissioning her freshwater system, the temperature was in the mid-60s, with a light breeze, flat seas, and a cloudless sky. Still, we all knew change is the rule this time of year, not the exception. In Quincy the leaves were at peak color, but Rick and Jim said the best leaf viewing was farther north and east, along the Merrimack River. We hoped the color was still there and the weather would hold until we arrived.
An hour out of Quincy, we hit Marblehead, which—much to the consternation of Newport, Rhode Island, and Annapolis, Maryland—touts itself as America’s sailing capital. Sailors are notorious late-season boaters, but as we turned into the picturesque harbor, I saw barely a half-dozen sailboats. Even amid the maze of mooring balls it was still hard to grasp Rick’s claim that in midsummer 2,500 sailboats routinely cram these environs. On this day, only a couple of lobster boats were underway; even the launches for the blueblood Corinthian and Eastern yacht clubs were idle. The town was quiet, too, but at least there were plenty of leaves on the trees.
Idling out of the harbor we all felt the change: Horsetails began to mar the cerulean sky, the leaves ashore were hustled by a freshening breeze, and the temperature had dropped. Weather reports had predicted a cold front, the severity of which depended on which one you tuned to, and by the time we idled into Salem a few minutes later, the sky was leaden and the sun had disappeared. Jim was sullen but Rick was cheery: “If one word describes New England fall weather it’s changeable.”
Salem was as busy as Marblehead was quiet. There were boats in the water, the waterfront restaurants were crowded, and tourists strolled the breakwater gazing at Friendship, the 171-foot three-masted East Indiaman replica. Along with The House of the Seven Gables, it’s the big waterfront draw here. But it still didn’t explain all the tourists on this now-blustery day. Then we remembered: Halloween was a week away, and what better place to get inspiration for your witch’s costume than Salem?
By the time we left the harbor, the weather was downright cold and threatening rain, so Rick throttled up our IPS 600s and we beat it to our overnight stop, Gloucester. Despite 3- and 4-footers, the 420 managed a comfortable 20 knots, and a half-hour later we pulled into what has become the prototypical American fishing village, thanks to Sebastian Junger’s The Perfect Storm. We grabbed the face dock at Brown’s, a popular but now-deserted transit spot not far from where the ill-fated Andrea Gail departed.
It didn’t take long to feel Gloucester’s authenticity. You see the fishing history everywhere. Industrial and gritty, the harbor’s filled with draggers whose rust-stained hulls bear witness to their hard times offshore. Finding a fresh seafood dinner was no challenge, and after satiating ourselves on catch mere hours out of the sea, we turned in. But before I did, I took a quick look aloft. No stars. It looked like rain.
The next morning I looked out of my stateroom window to see uninterrupted gray—a bad omen. But after I’d donned my glasses I realized I was staring at the weathered wood of the dock. Up top it was all blue sky and bright sunshine. Gloucester’s two windmills were turning briskly, so I knew it was blowing, but no matter. We were looking at a near perfect day for the run to the Merrimack.
Brisk fall weather stokes the appetite, so we motored across the harbor to Rocky Neck, an agglomeration of funky galleries and working shipyards, including the Gloucester Marine Railways, “the oldest working shipyard in America.” It was also home to Sailor Stan’s, the best breakfast in town. After coffee, eggs benedict, and autentico huevos rancheros, the crew’s verdict was unanimous: Sailor Stan’s is a must-stop.
To skirt the longer, rougher passage around Cape Ann, we headed northeast, up the Annisquam River, where we got a taste of real fall color amid quaint houses and pristine marshes. Exiting out onto Ipswich Bay, a 25-knot wind threatened to derail the 8-mile run to the Merrimack Inlet, but as soon as we tucked into the lee of Plum Island things laid down. By noon we’d cleared the inlet and were on the river.
Just inside, Newburyport was surrounded by colorful trees, and the farther up the river we went, the better it got. Not only that but the temperature had clawed its way back to 60. We’d reserved a slip at the Merri-Mar Yacht Basin because it’s a little north of town where it’s quieter and more scenic.
The next morning our gamble paid big dividends. The picturesque Merrimack was a riot of color and the light was perfect, all the way up to Amesbury. I desperately wanted to stop at Lowell’s Boat Shop there; it’s a National Historical Landmark where they’ve been hand-building traditional watercraft since 1793, but we had to get the 420 back to Quincy.
Our perfect weather held, and the run back was a sleigh ride. We couldn’t have asked for better weather. But I was reminded that it had been a gamble nonetheless when I checked the forecast before shoving off for home: a cold front was headed in with temps dropping to the low 50s and possibly heavy rain. Talk about a gamble paying off.
Story originally appeared in our sister publication Power & Motoryacht.