Bill Everdell, an author and retired history teacher, recalls the first time he pedaled out of his driveway in Edgartown destined for Brooklyn, N.Y. It was sometime in the 1970s, and he was returning to the city for a national labor relations board hearing about Saint Ann’s School, where he taught at the time.

“I went down to testify and I thought, oh, I’ll take my bicycle, that’s the easiest way to go,” Mr. Everdell told the Gazette in a recent interview. Two days and three ferries later, he arrived home in Brooklyn. The trip interrupted his summer-long teacher’s vacation, but spawned a tradition that now brackets his summers.

Mr. Everdell, 76, is once again getting ready to leave Martha’s Vineyard and go back to New York by bike. As he prepares for his annual farewell to the Island, he reflects on his longtime cycling tradition. His route and equipment have evolved over time, but he remains steadfast about bicycling the whole way — about 260 miles in all.

All smiles before he hits the road. — Jeanna Shepard

“He has to bike every mile,” his wife, Barbara Everdell confirmed.

First, he’ll take the fast ferry from Oak Bluffs to Quonset, R.I. From Quonset, he will cycle to Point Judith, R.I., where he will catch a boat that takes him to Block Island. He’ll take a ferry from Block Island to New London, Conn., and finally, a ferry from New London to Orient Point, Long Island. From there he will cycle to Brooklyn.

In the 1970s, he could complete the whole trip in as little as 26 hours. Now, it takes him four days.

He eschews planning ahead but is aiming to depart on Sept. 5, so that he can arrive in Brooklyn ahead of his wife, who will drive home. He wants to be there to help her unload their suitcases from the car.

“His fantasy is that he will be back in Brooklyn to get the bags out of the car,” Mrs. Everdell said. “But I usually hijack some guy to help me.”

He’s also reluctant to book places to stay in advance of his departure. This tendency has, in past years, forced him to sleep outside.

His trips overlap with wedding season and last year, when he arrived at Point Judith, there were no available rooms, anywhere. He decided he would sleep on the ground outside, but when the temperature dropped to 45 degrees and it started raining, he moved indoors and slept in a bathroom, which, according to his wife, “is pretty bad for a 75-year-old man.”

“He got to New York looking pretty bedraggled,” she said.

Have bike will travel. — Jeanna Shepard

He's still not sure where he’ll sleep next week. He supposes he’ll spend a night in Point Judith, a night in New London, and one on Long Island to break up the trip.

“I used to be able to bicycle the entirety of Long Island in a day,” he said. “Now it’s two.”

Mr. Everdell was in his early thirties when he first journeyed home on two wheels.

At the time he rode a conventional upright bicycle. He now touts the advantages of riding a recumbent, which he bought in the 1990s.

“It’s amazingly comfortable and it’s also fast,” he said, noting that his reclined posture presents less of a cross-section to the breeze, allowing him to move faster.

He usually rides alone, though his son, Chris, has, on occasion, joined him for parts of the trip. Chris considers his father’s slow speed a mixed blessing. Mrs. Everdell recalls hearing from her son while he was on the road with his dad.

“Chris calls me and says, ‘The good news is dad goes so slowly that nothing is going to happen to him,’” Mrs. Everdell remembers her son telling her. But he complained about how much time their slow pace caused him to spend in the saddle. “He said, ‘Mom, you have to understand, not even during the most difficult stages of the Tour de France are they in the saddle for more than four to five hours. And I have been in the saddle for 12 hours.’”

The Everdells’ ties to the Vineyard run deep. Barbara and Bill each spent childhood summers on the Island, where they both sailed. Years later Barbara recognized Bill at a picnic at Princeton, where he went to college. Their two children, Chris and Josh, were born on the Vineyard.

Mr. Everdell delights in talking about and reflecting on his bicycle trips. “It’s great fun. It makes for a fascinating little mini-vacation. If you go on a bicycle over a long distance, you see a completely different scene,” he said.

Barbara and Bill Everdell; his wife has grown supportive of his adventure: "He always turns up." — Jeanna Shepard

But there was a time when he would have to sneak in and out of his family’s summer home to avoid his mother, who was concerned for his safety.

“The only person in my family who objected to it was my mother, and so I used to bicycle into Cow Bay at a time when I was sure my mother wouldn’t be there to greet me arriving on the Island,” he said. “I kept my bicycling odysseys to myself.”

Technical upgrades over the years have contributed to his safety along the way. He’s loath to consult maps, but relies on a GPS device given to him by his sons. At the recommendation of a neighbor, he mounted a GoPro camera to his helmet. It captured a harrowing piece of footage showing a motorist deliberately, it appears, ramming into him and knocking him to the ground. Mr. Everdell pedaled away unscathed and continued his journey.

There are advantages to riding at night, Mr. Everdell said. “It’s easier to ride the roads when there is so much less traffic.”

He’s even been given his own police escort, in Suffolk County. “They were so fascinated by what I was doing. They just trailed me and when their shift was over, another car would pull up, because it was the most interesting thing that was happening.”

Panier bags that carry changes of clothing and gadgets, including selfie sticks, straddle his rear tire. He emphasizes the importance of balancing the weight of each sack.

“You need to balance them if you possibly can because one of the things I learned early on is if you are tilted just a little bit one way you will feel it in your back after about 25 or 30 miles. So you have to be absolutely straight up and down and balance the weight on your bike,” he said.

Next stop, Brooklyn, N.Y.

There was a time when Mr. Everdell traveled “the usual way,” he says, via car or airplane. But by now, the bike trip has become so ingrained as a summer tradition that he refuses to travel any other way.

“Every other form of transportation is so much less convenient,” he said.

He’s been cycling for decades and can remember when bike helmets were so unusual — and unfashionable — that his wife asked him not to wear his until he was a safe distance away from their home.

He has no plans to retire from cycling. “It’s absolutely my main mode of exercise,” he said. “I’ll keep doing it. What I like about it is it’s a lifetime sport and this is not true of a lot of sports.”

He might not have a choice, either. When Mrs. Everdell packs up the car, she has become accustomed to completely filling the front passenger seat, leaving him nowhere to sit. “He long ago ceded his right to the front seat,” she said.

Over the years Mrs. Everdell has grown reluctantly supportive of her husband’s bicycling odysseys.

“I always think, oh, I will never see him again. But it’s been about 45 years now, and he always turns up.”