Background photo by Tom Lyons

Charlie Tilton

Cuttyhunk Classic

Bartholomew Gosnold came over in 1602 and set up a colony on an island in a saltwater pond on the west end of Cuttyhunk, and they lasted five or six months.  That was the first English settlement in the New World . . . The old-timers, they had a tough time to survive, I’m sure. The only vegetables they had were what they grew and canned for the winter, and fresh fish in the summer.

The Tiltons came onto the Vineyard in 1674, I think—old Samuel came over. All the Tiltons in the area come from him. He had three sons—the Georges and the Freds and the Zebs came from one, and the Charlie Tiltons and the Bob Tiltons on Cuttyhunk came from another. My grandfather came over to Cuttyhunk in the mid-1800s. They must have been (fishermen) because that’s all there is to do on Cuttyhunk.

My mother was a lighthouse keeper’s daughter on Cuttyhunk back in the 1910s. And that’s how she met my father.

Charlie Tilton

My old schoolteacher used to call Cuttyhunk “an experience surrounded by water.”

I went to school on Cuttyhunk for those first few years . . . I couldn’t get used to all the kids around me when I went over to the Dartmouth school system (laughs). That took a little while. The Cuttyhunk school, at one time, had three people in it: my sister was in the sixth grade, I was in the second grade, and there was a little girl in the first grade, in this one-room schoolhouse. Once you graduated there, then you had to go off-island to live with friends or relatives to go to high school.

I spent every summer on Cuttyhunk until I was 22. I made enough money bass fishing to go to college. I went to college at the University of Massachusetts Amherst and got a bachelor of science in civil engineering. Every summer, I’d come back to Cuttyhunk and do a little fishing and guiding.

I always knew what I was going to do when I retired before I started work. And I never regretted it.


In August 1954, I was in the service and I was home for a 30-day leave. One day, my father told me, “Go down and tell the kids to stop swimming. There’s an 800-pound shark in the harbor.”

I went back to the fish dock, cleaned a small bass, and took it up to the head of the harbor. It was high tide, and I looked out and I saw the fin—the wake of the fin was heading right toward a small dock there. On the dock, there were two couples in bathing suits, probably in their late 20s. So I hollered down to them, “Don’t go in the water.” They asked why, and I said, “There’s a shark in the water,” as it’s swimming right toward them. They were only about a foot, foot-and-a-half out of water on the dock.

They said, “Where is he?” At that moment, the shark saw the dock and turned around, his tail came out of the water and splashed right up on the dock. “Right there.”

We rigged up a swordfish harpoon, got in the back of the Mackenzie, and harpooned the shark right in the back of the fish dock. Lo and behold, that darn shark went around the only piling that had a boat on it. So we rigged again, and this time we buttonholed him and fought him for two hours—we pulled him out onto the float stage at about 5:30. With the combined weight of the shark and the people on the stage, the float stage sank (laughs). The shark was 14 feet long and eight feet around the belly.

We didn’t know what kind of shark it was. We sent one of the teeth off to Woods Hole Oceanographic Institution, and they told us it was a great white.

That was quite an experience. But when you live on a small island, especially in those years, you had those experiences.


I head down to South Carolina around November 1. I try to get to Cuttyhunk around May 1 . . . As long as I can get up out of a chair and down to the boat, I’m going.

I came back to Cuttyhunk to do a little fishing and a little water taxi work. I love my water time. I don’t care what I’m doing on the water—I love it.

I have a 27-foot Nauset with a 225 horsepower diesel engine. It gives me about 14 knots cruising. I’ve had boats that have done certain things better, but this one’s a good boat. It always gets me home. And I don’t just go out when it’s flat and calm on a Sunday afternoon.

With a golf cart, you buy it for $3,000, you don’t have to register it, you don’t have to insure it. Within three years, it’s paid for itself—after that, you’re making your money back. On Cuttyhunk, you only have a mile and a half of road, so why would you need more than a golf cart while you’re here?

I have a house that was built back in 1980, and it’s on a piece of land that my family owned before. I bought it from my two aunts, and my father gave me his share . . . I have a porch that looks out over Vineyard Sound, and I can see part of Buzzards Bay. It’s beautiful—the only thing I can’t see is the sunset. But I see lots of sunrises.


Jeff is the Managing Editor for Cape Cod Life Publications.

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