Madison Bay and the Little Choptank

I was hoping to accomplish two things this trip: I wanted to do long row. And I wanted to sail out onto the open Chesapeake for the first time.

The forecast was for no wind before 11 a.m. I arrived at the landing in Madison two hours before. No wind, no problem. I wanted test my skiff, my DIY oars, and my own ability to get back home if the wind dies.

A little mishap at the ramp – the skiff would not slide off the trailer. I could see from the centerboard’s lanyard that it was in a downward position. I must have left the CB down when I landed after my last trip. Loading onto the trailer had worked fine; the CB rotated up when the boat slid forward. But when sliding back off the trailer, it dropped enough to make the boat stick.

It took me 20-30 minutes to row out to the buoy at the mouth of Madison Bay. About 3 kts in flat water. The skiff rowed easily and tracked well. But my oars need to be lighter and a bit shorter.

When I kayaked here in the 90s, I was fascinated to see crabs and grasses on the bottom that glided 3-4 feet beneath me. Now I could only barely see the bottom through green water. No crabs or grass. I wondered about the health of the Little Choptank River Sanctuary.

I paused for breakfast near the buoy. Back at Madison, the wind turbine started turning slowly at 1050. Then it stopped at 1110. But a light breeze touched the water where I was at the edge of the larger river. I could see the Western Shore 5-6 miles off. The forecast made me expect a long reach out past the mouth of the Little Choptank and back. But it turned out quite differently.

The forecast for noon still said 8 kt from the north. I raised sail but went nowhere. So I rowed downriver to the next buoy. When the wind finally came up, it was from the west. It stayed that way all day. So it was a long beat to windward if I would finally reach the Bay.

I tacked back and forth out past Ragged Island and reached the channel marker at the mouth of the Little Choptank about 2pm. Then swung over to the mouth of Woolford Creek to stop for a late lunch. I didn’t find the shelter I was looking for. Still, I hove and was able to keep the sail up. The skiff kept bow to wind and small rolling waves while I did crackers, cheese, and zinfandel.

It was a run back to Madison Bay. By this time, the wind had backed around to the south but was finicky both in direction and strength, as I was close to the south shore.

A dinghy cast off from a yacht anchored at the bay entrances. It crossed my path 100 yards ahead. The oarsman landed on the marsh beach and let his big dog out to run and fetch sticks.

I watched how this sailboat and one other in the bay rode at anchor. And I watched yard flags a mile off. And when I rounded the point to see Madison, I watch the direction and speed of the wind turbine. All to keep gauge of the wind. I was a bit concerned about getting back to the landing before dark.

Wind and sail crucial during last 90 minutes back to port. Watched two anchored yachts for wind direction at the mouth and farther into Madison Bay. Then watched the windmilll speed and direction. Both yacht and windmill swung 90 degrees and back.

How important this was for sail and oar. It was dark by the time a got to Cambridge 12 miles up the road.

Duration: 8 hours
Distance: 16 miles
More photos and videos are here.


I also write about traditional Eastern Shore sailing workboats here.

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