Olive Tomlinson remembered birthday parties in Dorothy West’s backyard and performances at Shearer Theatre. Skip Finley recalled the thrill of being allowed to go to Circuit avenue at night, even as a 10 year old. Gretchen Tucker Underwood talked about wearing inverted sailor’s caps after swimming and finding a house party on summer evenings, no invitation or call needed.

For all three, childhood summers meant Oak Bluffs, moving in the orbit of the tight-knit community of African American summer residents who came to the Island each summer.

Ms. Tomlinson, Ms. Tucker Underwood and Mr. Finley, all full time Vineyard residents, shared memories of their Oak Bluffs childhoods, and their families’ enduring ties to the Vineyard, in the Gazette newsroom Tuesday as part of the paper’s winter speaker series. This month’s panel discussion began with a screening of a short film shot last summer by a French production company. The film gave a brief overview of the African Americans on Martha’s Vineyard, from days when black men worked on whaling ships to the emergence of Oak Bluffs as a summer haven for African Americans.

“It was a wonderful, wonderful childhood,” Ms. Tomlinson said. “We never had to go out of our circle, and because of the richness of the circle we never wanted to.”

“You could stop by somebody’s house, sit on the porch, have a drink,” Ms. Tucker Underwood said.

Olive Tomlinson, Skip Finley and Gretchen Tucker Underwood speak at Tuesdays in the Newsroom about how their families first settled in Oak Bluffs. — Mark Alan Lovewell

The name of the event was How We Got Here, and each speaker told the story of their family’s arrival on the Vineyard.

Ms. Tucker Underwood’s great-aunt Maude Fitzgerald, a certified public accountant, came to the Vineyard in the 1930s to do some books for a client, and decided to look for a place herself. At that time, she said, black people could not buy houses in the Camp Ground. “She did a little trick which many did for many reasons,” Ms. Tucker Underwood said. “She bought a Camp Ground house and moved it to the wooded section of Oak Bluffs and she thought this is it, now we’re here.” Every summer, she said, her father and his five brothers and sisters, who were orphaned, spent the summer on the Vineyard with Aunt Maude, and her father, who retired as a judge at Edgartown district court, kept coming, eventually buying the house and continuing to buy land in the area. “So that’s how we got here,” she said.

Ms. Tomlinson’s family connection began as part of the extended Shearer family, who owned a cottage in Oak Bluffs and later started the Shearer Summer Theatre Group. Her father once drove composer Harry Burleigh to Shearer Cottage, she said, or so the story goes.

“The beauty is every summer, there were lots of aunts to take care of you,” she said. “Our parents did not hover over us. They absolutely let us go. And they let us go because they did not want us underfoot. Because we were the Shearer kids, they had a hotel to run, they didn’t want us there...they said go, kids, go! And we went.”

Mr. Finley said his parents and their friends, the Margetsons, started coming to Oak Bluffs in the summer of 1955. His father eventually purchased a house a block away from Inkwell Beach. “Inkwell was my job,” Mr. Finley said. “At 10 a.m. I was on that beach and at 6 p.m. I was requested to go home.”

“I did all the kind of things kids today still do, except coin diving,” he said. “We picked blueberries, rode bikes, got a summer job, worked at Ocean View Hotel, Gio’s, the bowling alley, all those things combined, you could buy your own clams and french fries at Gio’s and go to the movies, meet girls.”

Ms. Tucker-Underwood said her great-aunt considered swims in the ocean as good as baths. Ms. Tomlinson, too, said that summer meant two baths, each before family birthday parties. She brought a photo of herself surrounded by family and friends in Dorothy West’s backyard. “This was after having a bath,” she said. Another photo showed Ms. Tomlinson, five years old, posing with a cigarette and a glass of vodka. “That’s the kind of family we were,” she said.

There was a distinction between city kids, who didn’t know how to swim or wore decorative bathing suits, and the Oak Bluffs summer regulars.

“Black women have a thing about their hair, and getting their hair wet,” Ms. Tucker Underwood said. “To go swimming at Inkwell was quite a ritual, so when you got out of the water your hair looked as fly as when you went in.”

The answer was inverted sailor caps. “That was the thing. Decorate the cap, your name, your boyfriend’s name, or whatever,” she said. In the water “we learned how to swim, dog paddle, just don’t get the hair wet. That was the way we lived.”

Mr. Finley and his friends went down to the Steamship Authority to check out the girls coming to town. Ms. Tomlinson said she met the sons of men who worked on her family’s cottages. “My aunts trusted the workmen, the workmen had sons...so the sons became our swains,” she said. “These were the Island boys...which was a big deal. They had cars. The city boys didn’t have cars. The swains had them and they were afraid of our parents and so they treated us nicely, and it was a great summer experience.”

In some ways the Vineyard was a respite from racism in post-war America, the panelists said, but the Island wasn’t immune from those realities. When her great-aunt looked for a house, Ms. Tucker Underwood said, some houses were off-limits. Some homes had codicils prohibiting sales to black people, Jewish people, or anyone who wasn’t a Caucasian of Protestant faith. But real estate agents who would help black people buy homes were well-known, including some who would buy houses themselves and then sell them back to clients. Black families wanting to purchase homes had to lay the groundwork, Ms. Tomlinson said. “You don’t walk into a place and say, here I am,” she said.

Other parts of the Island could be less friendly, Ms. Tomlinson said. Word was that Edgartown police at that time had a code — a red car is coming — that meant black men were coming into Edgartown, she said. “So there was no reason for us to go.”

“We laugh when we hear there is no racism,” Mr. Finley said. “It doesn’t mean racism like overt.”

“I grew up in segregated Boston,” Ms. Tucker Underwood said. “So when I came down here....why would I want to go anywhere else, why would I care if I wasn’t welcome somewhere else. On the Vineyard, folks like this, I’m glad to see them.”

Other memories are idyllic. Tennis was a big part of summer life, Mr. Finley said. Ms. Tucker Underwood’s family had a court, and her mother has the longest running tennis tournament on the Vineyard, she said, running some 40 years. Sen. Edward Brooke, an Oak Bluffs summer resident, held a big tennis tournament every Labor Day. “It was a three or four day spectacle,” Ms. Tucker Underwood said. “People kept looking the whole year, what’s the coolest white outfit we can find.”

Senator Brooke’s number was listed in the phone book, Ms. Tucker Underwood said, and he knew that the best flowers in town grew at the dump.

“The man was actually a senator and he was still Uncle Ed,” Mr. Finley said. “He rode his bike into town.”

The three reflected on changes to their summer haven over the years, now that younger generations of their families are spending their own summers on the Island. Ms. Tomlinson lamented the discrepancies between rich and poor. “I hate the size of the houses now,” she said. “We lived in houses with no heat. I loved that.”

Ms. Tucker Underwood said the Island housing shortage worries her, with a lack of housing for teachers, police officers and hospital employees. “We want the diversity in a number of places but people who want to come here can’t afford to,” she said.

The town police force has changed for the better, Mr. Finley said, including the legacy of former chief Joe Carter.

Ms. Tucker Underwood pointed out that Oak Bluffs police chief Erik Blake, who is white, is the president of the Martha’s Vineyard NAACP.

“Only in O.B.,” Mr. Finley said.