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It was the autumn of 1965, and word around the boathouses along the river was that there was going to be a new regatta patterned after the Head races in England and that the organizers wanted to fill up the field. Thomas Crosby, who was born at the start of the century and had been paddling out of the Union Boat Club for decades, signed on.

So did his son, who’d gone off to the Navy after Harvard and had been messing about in boats since he was a kid.

“They said, ‘Hey, we’re going to have this race and it’ll be fun and it’s something Boston needs to have,’ ” recalled David Crosby, who rowed in the junior single. “And it caught on very quickly.”

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The Head of the Charles goes off for the 50th time this weekend and it has become so popular — 11,000 rowers from 28 countries competing in front of an expected 400,000 spectators — that the 76-year-old Crosby had to win the lottery to get into the senior veteran singles event. When his father competed in the inaugural race — when anyone over 40 was deemed a veteran — only 11 men turned up, all but three of them from Union or the Cambridge Boat Club.

Thomas Crosby competed in the regatta until he was 89, long enough that grandson Josh was tapped to serve as his unofficial “escort,” rowing a single ahead of him as a precaution. Josh went on to stroke the US eight to the gold medal at the 1992 world junior championships and rowed for the Brown heavyweights, but his Head debut was a family affair.

The tradition continues Saturday when David, despite an uncooperative knee, takes to the water in the morning and 40-year-old Josh strokes Union’s master eight in the afternoon.

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“What I love about my dad is he can only row like half-slide now so he’s at a complete disadvantage,” Josh said. “But where most guys would be, ‘I’m too slow, I’m going to get beat, I can’t row, why do it?’ he’s like, ‘What the heck? I’m going to train, I’m going to have a goal and I’m going to give it my best.’ That’s the true athlete, in my mind.”

David’s primary sport was hockey; he played forward for Harvard’s varsity. Rowing was his cross-training activity and the source of his spending money, since he taught basic sculling at Weld Boathouse. He did endurance workouts for fun, riding his bicycle from Auburndale to the boathouse on the Esplanade, then biking back, or rowing up to Annisquam and around Cape Ann in an ungainly tub called “The Albatross.”

So when his son wanted to play lacrosse at St. Paul’s School in New Hampshire, David urged him to give rowing a try.

“He said, ‘Just give it two weeks and then go back to lacrosse if you want,’ ” Josh said. “I did a day of horrible, grueling dry land and I was hooked. There was no turning back. I just loved it.”

Yet it wasn’t until 1997, when he raced with the US lightweight team, that he made his official Head debut. St. Paul’s didn’t compete in the regatta and Josh never got the chance at Brown.

“The first year, they messed up the entry,” he recalled. “The second year, I was too old for the youth eight. The third year I was in Denmark. The fourth year I decided to row the single and we got stormed out.”

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By then his grandfather’s days on the Charles were done.

“He rowed until the Head organizers thought it was a liability and encouraged me not to have him do it the next year,” said David, “so we curtailed that.”

As a substitute, Thomas competed in the CRASH-Bs, the unofficial world indoor championships.

“He was the only cat in the category,” his grandson remembered. “When he went to register and they asked what age group and he said 93, they said, ‘Ahh, we don’t have that age group.’ He said, ‘Well, you better make one because I’m here to race.’ ”

The elder Crosby’s longevity (he lived until 98) was so impressive that the grand veterans trophy, for what customary victor Richard Kendall calls the “80-to-oblivion category,” is named after him. David, who has had hip and knee replacements, isn’t sure he’ll go the distance for that long.

“I don’t make predictions,” he said. “I’ll row as long as I feel safe doing it and as long as other injuries don’t bother me.”

David still is feeling fit enough that he’ll row 250 miles a year, coming down from Manchester-by-the-Sea a couple of times a week for 10-mile workouts on the Charles. And because he got lucky in the lottery, he’ll get to take the line for the 50th edition of the world’s most fabled Head race.

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His first one was sabotaged by a broken seat axle around Magazine Beach and he finished last in the 17-boat field.

“I had to not flip over,” David recalled, “and finish the race using only my upper arms.”

This time, the concern likely will be more about the knee than the seat.

“My dad’s like, ‘Well, I’ll probably come in last this year,’ ” Josh said. “I said, ‘Well, the first year you came in last. So the first and the 50th? That’s pretty consistent.’ ”

John Powers can be reached at jpowers@globe.com.