Category Archives: Sail Rig

Into the Great Choptank


The peril of waiting to set the rudder
Drifting like a traditional workboat to hoist sail
The power and beauty of well-shaped canvas.
Hambrooks Bar Light back from the brink of death.


This was only my third time sailing solo. First was on the narrow Tuckahoe. Next on the middle Choptank. Now I would sail out of Cambridge into the Great Choptank.

I launched at the public ramp at Great Marsh Park. I needed to row away from the ramp before raising the sail. I had no tiller keeper. Rowing with the rudder in place and swinging around would be a problem. So I decided to set the rudder after I was out on the water, before I raised the sail.

I rowed from the ramp so I was out of the traffic land and leeway to let the boat drift while I worked to get under way. First I had to set the rudder. I was out on the big Choptank in a chop. Just a foot or so, but it bounced my skiff so that I couldn’t get the rudder pintles into the very small gudgeons. I tried and failed, drifted toward the breakwater, and had to row farther out to try again. Cursing helped. I finally got the rudder set, attached the tiller, and got ready to raise the sail.

In the few times I’d launched before – always in brisk winds, I tried to stay headed into the wind. But this time I was following the advice of Roger Barnes in his Dinghy Cruising Companion – hoist the sail while drifting broadside to the wind [*] with the gaff and sprit laid out over the lee gunwale. The Roger Barnes tutorial [*] helped me here: Let the boat drift. Winds were only 5-7 kts, so I was confident to try this.

Letting the sail and spars pay out over the lee gunwale kept them out of my face and reduced the risk of getting knocked out of the boat. It also helped that I had rotated the mast so the halyard cleat faces aft. This keeps me out of the extreme bow, the small boat less stable, while I tie off the halyard. And I learned to secure the halyard around the cleat and cinch it down without figures eights. For quicker release.

A northerly breeze at 7-10 kts was forecast for most of the day. This would allow me to sail downriver from Cambridge and back on a beam reach. But once again, the real wind was different from the forecast. Once again, I started off beating into the wind. But this time was remarkably different. Since my last time out, I had learned a lot about my balanced lug rig. Most useful was the video tutorial from Michael Storer for the lug sail on his OzGoose design here. I learned to pull the downhaul down hard and secure it tight. With this, I sailed much closer to the wind.

From Cambridge to Dickinson Bay.

I naively imagined sailing as far as the Tred Avon and Oxford. Big short chop and westerlies from broad lower Choptank slowed me down, even with a more efficient sail. I saw that I need more ballast forward will give more speed through the chop – another day.. Just to cross the Great Choptank was a big deal for me today.

In the shadow of Howell Point, the wind shifted and danced from north to west and back. I anchored in Dickinson Bay for lunch in the shallows near a five-star goose blind.

While crossing, I kept an eye on the Hambrooks Bar Light to gauge my position and progress. After lunch, I set my course for the light. Back in April 2020, I had been contacted by Jim Malone, a lighthouse enthusiast from Connecticut, who said the USCG had awarded a contract for demolition of the light in June. He also contacted the Jim Richardson Maritime Museum in Cambridge and the Chesapeake Bay Maritime Museum in St. Michaels. Apparently no one in the local community was aware. I read later that Rep. Andy Harris got involved. So there it is, still.

Hambrooks Bar Light. Back from the brink of death.

From Hambrooks Bar, it was a leisurely run back to the ramp at Great Marsh Park. Outside the breakwater, I let the boat drift again broadside to the wind while I lowered the sail. Then I rowed in.


Duration: 3 hours
Distance: 7.5 miles
More photos and videos are here.

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[*] Everyone used to hoist sail this way

It has become the normal practice on modern yachts to hoist the sails while motoring to windward, but this is unwise in a sailing dinghy. The motion is atrocious in anything of a chop … It is better to row or motor your boat into a patch of clear water, and then hoist the sails while the dinghy is drifting. A drifting dinghy will tend to lie broadside onto the wind, so the sails must be hoisted while they are squared off over the side.

Traditional rigs are designed to cope with this. Everyone used to hoist sail this way, before the easy availability of auxiliary power started to erode traditional sailing skills. By contrast, many modern rigs seem to be designed with the expectation that the sail will only be hoisted while the boat is lying head to wind, otherwise the luff jams in its track or the mainsail headboard gets caught under the spreaders. This is why yachts usually motor to windward when they raise their sails and racing dinghies have got into the habit of hoisting their sails ashore in the dinghy park. Neither of these options is suitable for a cruising dinghy. It is vital that her sails can be hoisted and lowered when the wind is on the beam.

– Roger Barnes, The Dinghy Cruising Companion

Below Denton


Sailing where sailboats are no longer seen.
With a sail badly formed.
The harbor I might not escape from.
Feeling for the lightest breeze, in sight of home port.


High spring tide on the Choptank at Denton when I launched. The plan was to sail downriver a few miles to the ramp inside the mouth of Watt’s Creek at Martinak State Park.

The wind forecast was not ideal – gusts above 10 kts. But I had only been on the water a few times with my new boat, and I was eager to get back out. Besides, the river here is very narrow, so I would be protected from the strongest winds. And wind would blow across the river most of the way – a comfortable beam reach downriver and back. Or so I thought.

Of course, when a narrow river bends in three directions, even a steady wind will be from three directions. I got to try working all points of sail on this short passage. As the river widened below Denton, the wind gusted mostly from the southwest. So I was beating into the wind most of the way, on very short tacks, coming about within a few yards of powerboat docks closer to town and marshes down near Watts Creek.

I wanted to enter Watts Creek and picnic in Martinak Park. But when I approach the mouth, the wind was WSW and pushing chop up the creek toward the ramp. If I went in, I wasn’t sure I could get back out. I certainly couldn’t sail and tack my way out. And I wasn’t sure I could row out against the wind and chop. The track shows that I approached but thought better of it, swung around, crossed to the protected west bank of the Choptank, and anchored for lunch.

Lunch break across the river from Watts Creek. Looking back up the Choptank..

You can see from the next photo that I was only guessing how to reef a lugsail. I kept the gaff at the top of the mast and raised the sprit up to the reef points. I didn’t know how to use the reef tack and clew. Still, this is the sail that pushed me back upriver with the wind mostly from aft quarter.

The track here shows how I rowed straight downriver from the ramp. But on the sail back, my skiff turned and twisted looking for the breeze on that final 200 yards. This segment was perhaps the best part of the trip. I spent almost an hour making my way back to the ramp. I felt each promise of breeze coming between the trees and houses on the high left bank. Or from the marsh and cripple on the right bank. My boat spun in every direction while I coaxed lift from my sail. This is why I sail a small boat, engineless. And why I carry oars.

Duration: 4 hours
Distance: 5.3 miles
More images and videos are here.