Sailing the Downeast Challenge with my son

Photo by John MurrayThe author’s son, Matthew, as Crazy Horse approaches the Portland buoy in light air at sunrise.

June 2024

By John Murray

Editor’s note: this year’s Downeast Challenge, which takes place on July 26-27, is from Marblehead, Mass., to Portland, Maine. The following is a charming first-person account from one of the 2022 race’s participants, who ended up double-handing with his 12-year-old son.

In 2022, I planned to sail solo in the shorthanded division of the Downeast Challenge, an 80-mile race from Marblehead, Mass., to Portland, Maine. My Aphrodite 101, Crazy Horse, has a manageable self-tacking jib; however, I did not have an auto-tiller. After thinking about the value of an extra set of hands, I decided to recruit my then 12-year-old son, Matthew, for the race. He had sailed with me for years at that point, but rarely raced. As the weather forecast was mild, my wife reluctantly agreed.

We left Marblehead at noon on Friday in a light southeasterly, then popped the chute past Thatcher Island and headed towards Portland. That afternoon we caught a glimpse of a whale and noticed strange, brown seabirds floating on the water. The breeze kept dying and filling, so we set and doused the spinnaker about five times. Matthew controlled the spinnaker sheets with the tiller between his legs, while I managed the spinnaker halyard and sail. After the sun went down, we doused the spinnaker for the night, and Matthew made two Cup-o-Noodle soups for our dinner then turned on the running lights. After dinner, he made himself a cup of tea and me a cup of coffee. He had fun tidying up the boat and setting up his sleeping bag using the light from a headlamp. I told him he didn’t need to brush his teeth, and not to tell his mom.

Sailing in light wind for hours gave us lots of time to catch up on everything. We talked about the race, his friends and lots of other topics. We laughed reciting funny movie lines from “Dumb and Dumber” and “Napoleon Dynamite.” We sat silently listening to the boat moving slowly through the water. Matthew planned to stay up all night, but by 1:00 a.m. he crawled into his sleeping bag as I sailed on.

As we approached Portland, the wind died and we drifted. Matthew woke up around 3:00 a.m. and joined me in the cockpit. We noticed seagulls circling the stern of the boat, drawn there by the stern light and diving to catch unseen fish. We shined the flashlight at the gulls to shoo them away and laughed when one dive-bombed us.

As dawn neared, we saw the blinking white light of the turning mark off Portland and I instructed Matthew to steer (drift) toward it. I went below to catch a few winks as he captained the boat. At sunrise, I woke up and Matthew pointed to the other racing boats drifting nearby as I made coffee and oatmeal for breakfast. Eventually the wind came up and we rounded the turning mark and finished the past Portland Light.

We spent the day in Portland and I joked how he could not stay up all night, and he made fun of my snoring. At the awards party, Matthew collected our 3rd-place trophy in the seven-boat shorthanded division. The other father-son duo was David Carlen with his grown son on Arion, who won the cruising division. After the race, Matthew and I spent a fun week cruising Casco Bay sampling ice cream at every port. Mark Twain famously said, “When I was a boy of 14, my father was so ignorant I could hardly stand to have the old man around. But when I got to be 21, I was astonished at how much the old man had learned in seven years.” Matthew is now 14 years old and more interested in spending time with his friends and his iPhone than his old man. I wonder if I need to wait until he turns 21 to have such a memorable race again.

For more information go to: www.regattaman.com/new_event_page.php?race_id=474.

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