President Kennedy Slept in Room L at Ocean View, and This Is How It Happened, Rep. Sylvia Recalls.
The Visit of young Jack Kennedy to Martha’s Vineyard as a young yachtsman in the summer of 1941 hasn’t been forgotten. The adventures of the future President and his brother began before they reached the scene of the regatta at Edgartown.
An earlier part of the story is supplied by Rep. Joseph A. Sylvia, former proprietor of the Ocean View Hotel of Oak Bluffs, and his housekeeper, at the hotel, of that time, Mrs. Frank Silvia. For President Kennedy slept at the Ocean View, in Room L. But let Representative Sylvia tell of the event in his own words:
“It was in July, 1941, the time of the Edgartown Yacht Club regatta, and from a boat in Oak Bluffs harbor there came to the Ocean View two young fellows, teen-agers, dressed in suits of blue dungarees, bare-footed and bare-headed, and carrying a boat sail. They were as soaking wet as if they had been dropped overboard, their sail was also soaking wet and torn, they had no spare clothing nor even underwear, and explained rather piteously, that they had come from the mainland, bound for Edgartown to race.

A Tough Passage

“They had experienced a tough passage, and needed just about everything, including the services of a sailmaker to repair their sail in time for the next day’s race.
“We didn’t know who they were but I said to Mrs. Silvia, ‘We have to do something for them, they are only kids and in difficulties.’
“We gave them a room, and saw to it that there was plenty of hot water. We hunted through my son’s clothing and found underwear and other things that would fit them. We dried out their clothes in the meantime. They had errands to do and went about them.
“I didn’t know where a sailmaker might be found, but they asked if there was a tailor and someone told me that Issokson in Vineyard Haven sometimes repaired sails. I called him and at first he said that he couldn’t possibly find the time, but eventually he said that perhaps he could do it at night, and we took the sail over.
“In due time the boys got hungry and wanted food, and we had to hunt them up some shoes and stockings in order to make them presentable in the dining room. So everything went very well, and finally when they confessed to the girl at the desk that they had no money, but that their father would take care of all expenses, we tool them on their word.

No Idea He Was Future President

July 29, 1941 Vineyard Gazette
“They left us, for Edgartown, in far better condition than when they arrived, and I should add that we sent out the bill and it was paid in full. We knew, by that time, that they were Joseph P. Kennedy Jr. and John F. Kennedy, but we had no idea that we had been entertaining a future President of the United States.”
Accordingly, when Jack Kennedy sailed his Wianno to victory at Edgartown, it was under a sail mended by Issokson of Vineyard Haven, and after having been sheltered by Joseph A. Sylvia, at the Ocean View, on his way to Edgartown.
If the present proprietor of the Ocean View cares for the notion, he has a bona fide right to hang a tablet on the door of Room L, stating that “President Kennedy Slept Here. He did, indeed.


From the January 26, 1962 edition of the Vineyard Gazette:

President Checks on Facts - All O.K. but Identity of Companion

First hand corroboration from the White House of the fact that President Kennedy slept at the Ocean View in Oak Bluffs on a yachting adventure long ago was received by Rep. Joseph A. Syliva this week. The corroboration came through Mr. Syliva’s son in law, William A. McMahon, who knew the President in prep school and wrote to him the other day, enclosing clippings from the Gazette, recounting details of the visit.
From the President’s personal secretary came a friendly not to Mr. McMahon. President Kennedy had enjoyed reading the clippings, the note said, and offered one correction.
It wasn’t President Kennedy’s brother Joe who accompanied him to the Edgartown regatta that summer of 1941, but Congressman Torbert MacDonald. For those who may wish paste this in their history books, Torbert Hart McDonald was born in 1917, attended Phillips Andover, was graduated from Harvard and Harvard Law, was a lieutenant (j. g.) in the Navy Reserve from 1942 to 1944, and like President Kennedy, commanded a P. T. Boat. He is now congressman from the eight Massachusetts district.
Representative Sylvia owned the Ocean View at the time of the visit of the future President.