Gerald Jeffers, a Chappaquiddick native who traced his Island Wampanoag roots back more than 200 years, died Monday at the Massachusetts General Hospital in Boston from complications following a car accident. He was 84 and was a legendary figure on Chappy, the small, close-knit island situated off the eastern end of Edgartown.
Although he would no doubt shun the moniker, Gerry was a Renaissance man in the true Island style. He repaired cars, ran a small gas station, store and junkyard for many years, drove the Chappaquiddick school bus, plowed the Chappy roads, and was a volunteer fireman and a deputy sheriff for Dukes County.
He quite famously was a master at driving on the beach, and knew the rural roads, fields and beaches of Chappaquiddick like the back of his hand, from a lifetime spent exploring them.
“There is always something new you see,” he told the Martha’s Vineyard Magazine in a 1991 interview.
He was also a master mechanic and started driving at the age of nine. Soon after that he began taking cars apart and learning how to put them back together again. His formal training was at a garage in Edgartown and in the U.S. Army, where he served two tours overseas in the 1950s during the Korean War.
Gerry was born on Nov. 25, 1932, the only son of Gladys Jeffers, a Wampanoag. In a 2001 interview with the Martha’s Vineyard Museum’s oral historian Linsey Lee, he said he never knew his father. He grew up on Chappaquiddick where his mother, aunt and grandmother ran the Chappaquiddick Outlook, a restaurant on the family homestead overlooking Cape Pogue Pond. He was educated at the Edgartown School, later did military service and returned home to Chappaquiddick where he worked as a mechanic and drove the school bus for decades.
On an island surrounded by many miles of soft-sand barrier beaches, his skill at beach driving was widely known and admired. And when other drivers became stuck on the beach, Gerry would inevitably be called to pull them out.
“He can point to every break, and tell a soft spot in the sand by slight shading. He is so good he doesn’t even need four-wheel drive,” the 1991 magazine story reported.
In one well-told story, a pair of summer residents were trying to get their station wagon to New York city in the dead of winter one year in the 1970s. The harbor was frozen over and the Chappaquiddick ferry wasn’t running. Gerry drove the couple’s two-wheel drive car across the barrier beach that connects Chappaquiddick to Edgartown. The story was true, although like many Vineyard tales, it has taken on variations and embellishments through the decades.
In the interview with Ms. Lee, he recalled his early experiences driving on the beach.
“We didn’t have a Jeep, I used to have an old Model A Ford with big tires on it, that’s what I used for beach buggies,” he said. “I think it worked better than Jeeps, because it didn’t leave a track.”
He was married twice; his second wife, E. Mae Jeffers, died in 1989. They had three daughters and a son.
A lifelong ladies’ man, Gerry loved to flirt and had a twinkle in his eye. His longtime companion Cynthia Schilling survives him.
He was also a familiar figure on the Chappy ferry, the small, three-car barge that plies the channel in the Edgartown harbor. It was an unwritten rule that Gerry could raise and lower the ramps and put the chain down, even though he was not an employee. “See you later, Rockefeller,” was his familiar goodbye.
“Gerry Jeffers was a man of very few words. For someone who said so little, he had a huge number of friends and acquaintances,” said Peter Wells, co-owner of the Chappaquiddick Ferry, in a statement Tuesday. “His family gives their thanks and appreciation for the overwhelming outpouring of well wishes, visits, cards and prayers from so many during the past weeks. He filled a special niche in our hearts, in our lives and in our community. He had a good long run. See ya later, Rockefeller!”
Visiting hours will be held on Thursday, Nov. 2, from 4 to 7 p.m. in the Chapman, Cole and Gleason Funeral Home in Oak Bluffs.
A funeral service will be held at 9 a.m. on Friday, Nov. 3 in the Old Whaling Church in Edgartown. Interment will follow in the New Westside Cemetery.
An obituary will appear in the Gazette next week.
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