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Favorable winds and four days of cruising

My first cruise of the season was like many others before it in one respect, the destination, but totally different in another because there was wind — and plenty of it. I set off May 25 from Annapolis under sail, bound for Oxford once again.

The Bay Tripper had plenty of wind for his first cruise of the season.

But I soon ran out of wind and began motorsailing south toward Poplar Island on the Middle Eastern Shore. It was a bad omen, but I suspected wind conditions might improve once I transited Knapps Narrows on Tilghman Island and entered the Choptank River. Knapps can be a tricky place because of sometimes-strong currents, which is one reason that stowing all sail makes good sense.

At the bascule drawbridge, the scene had changed somewhat in that the picturesque but dilapidated Crow Brothers buyboats are gone, leaving more room to maneuver while waiting for the bridge to open, which it does frequently. Also, the old Bridge Restaurant has closed, and the nearby Bay Hundred Restaurant on the north side of the Narrows has taken up any slack with a long floating dock and slips.

Nearing the Choptank exit, I began raising the mainsail and, as expected, was greeted by a 12-knot breeze from the south. I rolled out the jib and was soon flying along on a starboard reach toward Oxford’s Benoni Point at the mouth of the Tred Avon River, some 10 miles distant. Several other sailboats that had tagged in the Narrows did not raise sail and continued to motor, which was a mystery to me, although there was a threatening dark cloud lurking in the east that disintegrated peacefully.

I always cut way inside Benoni’s No. 1 marker, even though the chart reads 2 feet, and soon I was sailing wing and wing toward the Town Creek entrance. I sometimes think my boat knows the way here as much as I do. The bucolic farm scene along the north side of the creek has changed for the worse, I think, with the farmland replaced by several mega-mansion estates, but the lovely village on the opposite side is as charming as ever, I am pleased to report.

Through the years, I have come to know and love the timeless and unique Cutts & Case Shipyard, long a landmark family operation and run by the colorful Cutts brothers, Ronnie and Eddie, since their legendary founding father, Edmund Sr., died in 2010. This is a haven for wooden yachts, some of relatively recent vintage and some of age dockside and on land. This time around, I counted nine upright varnished spars and several more freshly varnished ones laid out on sawhorses. Two wooden boats awaited launching by an ancient crane — one freshly brushed white and the other sprayed black. I photographed my clear image in the deep, mirror-like blackness of Seabird and avoided running my fingers along the flawless hull.

There are mystery boats (to me, at least) on land that have been stored here for years, and I often wonder about their history. They must be objects of great love and affection, and they repose in frozen tranquility under a high roof, protected from the elements. A resident boat owner told me that the brothers recently broke up two old wooden boats, and I got curious about their stories. I tried to get an answer from Eddie, but I could understand why he didn’t respond to my request. It was clearly a personal matter.

In a wood burn pile, I spotted a long handrail from a dead boat and made a request to save it from the shop’s wood stove but got no answer. I’m not sure what I would have done with it, anyway, other than refinish it just to save it.

At most boatyards, the premises are locked after hours. But not here. So if I have a minor chore to undertake, I can use a large, old vise or a few tools, as long as I return them. This time I used a punch to cut some round holes in an elk hide wrap around the end of my tiller. It’s always easier when you have the proper tools for a job.

The Cutts brothers invite me to tie up whenever I visit, and if I’m lazy after my 28-mile trip, I usually take them up on it. There’s a hot-water shower and usually a spare bicycle to borrow and pedal about. I know most restaurants here will serve tasty local crabmeat and not the less-tasty imports, so I don’t embarrass myself with the standard question I ask elsewhere: “Where is the crabmeat from?” I am not much of a cruising cook, incidentally.

The next day, after buying gas and block ice, I left early for Cambridge, where I could find freshly steamed local crabmeat at J.M. Clayton’s crab-picking house, billed as “the world’s oldest crab house” (since the 1890s). A short sprint there began under sail at 9 a.m., but the wind soon deteriorated and I was cursed with motorsailing to get the jumbo lump I would eat for lunch dockside, fresh out of the container with crackers.

But sailing was more important than food, and when the southerly began stirring behind me off LaTrappe Creek I turned around and canceled Cambridge. I sailed rail-down on a port beat toward Cook Point at the mouth of the Choptank, which is marked by a few spindly trees at land’s end that seemingly grow out of the water. I’ll bet that within a few years they will have disappeared, victims of the rising water table. The same thing happened at the tip of Benoni Point, once marked by a few trees that are now gone.

As it turned out, I spent the entire afternoon sailing around the Choptank and in and out of Broad Creek, which is flanked by almost a dozen creeks and coves — one with the delightful name Solitude that I have yet to visit. The lower Choptank offers dozens of such creeks and coves for anchoring, some of which are private markers placed by locals for tight navigation. Warning: Don’t confuse a green or red crab-pot marker with a green or red nav aid.

That evening, favorable winds returned me to Town Creek and Cutts & Case, instead of anchoring in Dunn Cove off Harris Creek near Knapps Narrows, as I originally planned. On the final day, a strong southerly blew me back across the Bay to the Western Shore and Galesville on a broad port reach, where the sailing urge first captivated me more than 40 years ago and where old memories are always stirred up. On Memorial Day it was back to Annapolis after nearly four full days of wind from a favorable direction.

Jack Sherwood is writer at large for Soundings.

This article originally appeared in the August 2012 issue.