Gunkholing: A Special Memory

Cape Cod Life  /  November/December 2021 /

Writer: Brian Shortsleeve

In this holiday issue of Cape Cod Life I would like to share with you my column from the holidays in the year 2000. 

This column from 21 years ago catches a great glimpse into what life was like for Judy, me and our two sons, Joshua and Maxwell. And, I must first explain, when the boys were born we named them Joshua and then Joel. Joel’s nickname quickly became Jo Jo. However when he was three years old he told Judy and me he was changing his name to MAX! We thought his idea would pass. However, two years later he was starting school. The school contacted Judy and said he was going through school by a different name than his birth certificate showed. Judy, Max and I went to court and changed his name officially to Maxwell.

This column from year 2000 leads up to what I refer to in the column as “…the high point of the boating season for me.” A very special time to remember.

Max held onto this toy boat for many years. After we moved one or two times and Max went off to school I ended up saving the toy boat and toy boat memory.

When we just moved to our new home in September of this year, Max was helping us pack and move, and I offered the boat back to Max. Joshua, one of our best photographers took this photo for me, capturing the moment!

Thank you Josh and thank you Max.

My Best,

Brian Shortsleeve

Publisher, Cape Cod Life Publications

Photo by Josh Shortsleeve

The Top of the Hill

At the outset of the boating season which has just ended, Judy and I agreed that both of our boys were now old enough to do some cruising aboard The Lady Carline. Joshua, who is six, knows the boat well; Jojo who is three, loves to climb aboard, but his longest stint has been the occasional over-night. This year, our longest cruise was eight days; the boys loved it, it wasn’t all easy, but it was very rewarding.

We made it very clear to the boys that each promised departure was dependent upon safe boating weather. While underway, Josh would look to the horizon and say, “Pop, I think those might be storm clouds.” Jojo would observe the waves, point and ask, “Mom, is the wind blowing this way?” Josh looks to the sunset and says “Red sky at night, sailors’ delight. Red sky in the morning, sailors’ take warning!” Jo observes the early morning harbor and comments, “The water is calm as glass.” They both talk about “fog rolling in.”

Their innocent enthusiasm for boating, for Cuttyhunk, for being outside, for carefree schedules, reminds me of Judy’s and my cruises aboard The Lady Carline for many years.

After days of preparation, the moment comes. We drop the mooring lines, carefully wend our way through Megansett Harbor and into Buzzards Bay. Almost immediately we see the Cleveland Ledge Lighthouse, the first major marker of our roughly 21 nautical mile run to the island of Cuttyhunk. Almost immediately someone asks, “How much longer will it take to get there?” Just south of Woods Hole we can detect Cutty as a greyish line on the horizon, and growing. It’s great fun to see the gleam in the boys’ eyes as we enter the harbor, tie to a mooring and wave to friends. 

Joshua wakes up early, like me. One of his favorite things is for Josh and me to sneak out while Judy and Jojo are  still asleep. We whisper while dressing, quietly climb down into our dory, push ourselves off and drift silently away from The Lady Carline. Only when we are beyond earshot do we start the outboard on the dory. We tie up by the small bakery at the Fish Dock for a private picnic of cinnamon buns. A little later, all four of us visit The Cuttyhunk Fishing Club (B&B) for a full breakfast. After eating, the boys run and play in the huge yard overlooking Vineyard Sound. At the edge of the bluff high above the beach, with a view to the Gay Head Lighthouse, we sit in Adirondack chairs feeling the morning sun, the four of us quiet for a moment. 

Mid-week we sailed over to the Vineyard for a few days. A brisk breeze blew from the Northeast; there was enough chop on the Sound for waves to splash over the bow and onto the windshield. The boys said they were riding bucking broncos. Cutting across the waves the four of us were singing, “This old man, he played one… this old man came rolling home.” Menemsha gradually grew into focus, and we eased into the harbor.

Jo and Josh couldn’t wait to go exploring… along the dock, past fishing trawlers, behind fish and lobster markets, past kids crabbing, over the high lookout hill and down to the Coast Guard dock, just beyond the Mememsha Market general store, where they sell penny—I mean nickel—candy. One morning it was raining; we taxied over to Oaks Bluffs so the kids could ride on the Flying Horses Carousel and grab for the brass ring. The sun popped out, we watched para-sailors go up with colorful parachutes, and big rigs load onto the freight ferry. Judy’s brother Bill, who lives on the Vineyard, joined us for dinner at Lambert’s Cove Country Inn. 

Late in the week we returned to Cataumet by way of Cuttyhunk, where we had a couple of days of beautiful end-of-the-season beach weather. I would say we had a marvelous summer, but I have to share with you the high point of the boating season for me.

One morning at Mememsha general store, Jojo, our three-year old, picked up a purple toy speed boat and asked me if he could get it. I said, “No, I’ve already bought you some candy and you know the rule—one thing!” He asked if he could put the candy back. I said “No, we have already paid for it.” We stepped outside the store; he turned and buried his face against me and began to cry. I told him that if he were to be good all day, we could return to the store later and buy the speed boat. He was good all day and reminded me more than once. Late that day, he and I hiked over the lookout hill up to the store with the purple boat. On the return trip, we were atop the hill with a postcard-perfect view for miles around; we were quietly walking hand in hand. The speed boat was clutched very securely under his right arm. With his left hand , he brought my hand up to his face, and without a word he kissed my hand. 

The warmest of holidays to your and yours.

My best,


Brian Shortsleeve

Brian Shortsleeve is the owner, publisher, and founder of Cape Cod Life Publications. His personal column, “Gunkholing,” has appeared in all issues of Cape Cod LIFE since the very first issue in 1979.