It was intended as an insult. It turned into a legacy.

Lore has it that in the mid-1950s, a group of white women were walking down Circuit Avenue in Oak Bluffs, complaining that the Black families of Martha’s Vineyard – who were mostly homeowners but summer residents – were good for showing up and enjoying the place, but what did they give in return? They didn’t contribute, really. They didn’t give back.

Thelma Garland Smith, an educator who grew up in Boston, was one of those Black summer residents. She and her friends were also walking down Circuit, and they overheard that conversation. Garland Smith took that volley as a challenge.

She gathered about a dozen Black homeowners from Oak Bluffs in the summer of 1955, and a year later that group officially became The Cottagers, a philanthropic organization dedicated to the well-being of their Island community. (The name is a reference to their style of houses, which were often Island cottages.) Their first cash donation, given in 1956, was a $380 gift to Martha’s Vineyard Hospital, worth about $4,600 today.

Seventy years later, the Cottagers organization is still going strong, with membership capped at one hundred female homeowners devoted to philanthropy, fellowship, and fun.

Many of those early members were teachers, explained Patricia R. Bush, who has served as president of the Cottagers since 2023. As opportunities opened up for Black women in the workplace, the group also has included entrepreneurs, corporate executives, physicians, attorneys, accountants, and scientists. Yet the Cottagers’ mission has never centered on prestige or credentials; it has always been about giving back to the community they cherish and quietly doing practical work. 

“These are the Cottagers’ priorities,” wrote the famed author Dorothy West, an early Cottager, in a July 1972 column for the Vineyard Gazette: “To promote and help support financially worthwhile charitable and educational projects which improve the quality of living in the community; to promote interest in and to cooperate with other agencies in programs designed for community development, and to enjoy the fellowship inherent in the friendly association of the membership.”

Before that inaugural cash gift to the hospital, Garland Smith and her friends offered an even more practical gesture. Joanne H. Edey-Rhodes, the Cottagers’ chairwoman of history and archives, said that their first purchase was a garbage can for the town beach, since the white women also had complained that the shoreline was littered. 

Since those early offerings, the group has donated to the Martha’s Vineyard Boys & Girls Club, the Oak Bluffs Public Library, Island Grown Initiative, the Oak Bluffs Police and Fire Departments, and the Martha’s Vineyard chapter of the NAACP. “We look to see what’s going on with the Island, so we can meet the most critical needs,” said Karen Cole, chairwoman of the group’s community outreach and charity committee.

In recent years, that’s included a strong partnership with the Island Food Pantry. While many people’s lives came to a halt during the Covid-19 pandemic, Cole and her committee members were busy checking in with the food pantry and raising funds. These efforts culminated one Saturday last summer, when the Cottagers ran a food drive outside Stop & Shop in Edgartown and Cronig’s Market in Vineyard Haven. The group collected $1,015 in cash donations, $520 in online donations, 320 pounds of nonperishable food, and 150 pounds of essential items, such as hygiene products, cleaning supplies, and diapers.

“That was a highlight,” Cole recalled. “I was very impressed with the response from the Island; people really pulled together. It was nice to be a part of that.”

Along with the food pantry, Cole also listed the Cottagers’ scholarships (awarded to graduates of the Martha’s Vineyard Regional High School since the 1980s) and its relationship with the Martha’s Vineyard Cancer Support Group as its top priorities. The Cottagers provide money for people who need cancer treatments off-Island, helping with lodging and transportation.

Bush also noted the group’s relationship with Harbor Homes, a nonprofit that addresses homelessness on the Island. “We started that relationship about five years ago,” she said. “We have two seats on their board.”

Cottagers also spend time with the women at the shelter, “just being friends,” Bush said, providing an extra lift on holidays such as Valentine’s Day and Mother’s Day.

At its core, after all, the Cottagers is a social organization.

***

In the earliest days, Cottagers took turns hosting their meetings, opening their houses to the group. Members would take to each other’s porches, refreshments in hand, and debate when and how to raise money for various Island causes. After about a decade, when the group became too big for any one porch, it bought a building big enough to not only support itself, but to welcome in the public.

The Queen Ann–style building, on Pequot Avenue in Oak Bluffs, is a storied one. By the time the Cottagers purchased it in 1968, it had served as the town hall, fire station, and later a jail. 

After taking ownership of the building, the Cottagers used it as a meeting hall and an arts and educational center. It also served as a beloved dance hall for generations of summering teenagers. 

Nia Rhodes Jackson, one of those dancing teens, joined the group in 2010, becoming a third-generation Cottager. “Growing up, so much happened in that building,” she said, recalling the dances, art classes, fundraisers, and bridge games. “For me, the building has served as a center of activity.”

But in 2019, Bush said, a routine maintenance inspection detected a problem with the foundation, and the building was shut down. “Because of Covid and a lot of research on how to best shore up the foundation, it took a while to get the renovation moving,” she added.

The group started a capital campaign in 2020 to cover the costs, and it raised more than $1 million by 2025 with a combination of Community Preservation Committee funds, members’ donations, fundraisers, sponsorships, and outside gifts. A second capital campaign began this year, Bush said, and it seeks to raise another $1 million to pay off the renovation expenses and to create a capital improvement fund for the future, “so we don’t get in this place again,” she said. 

The work was scheduled to be finished this spring. Bush said they are planning a grand reopening celebration for June 24, open to the public, which will also highlight the group’s seventieth anniversary.

“We are so excited to be back,” she said. “We want to show off the building; it’s the heart of our organization.”

The Cottagers will resume using the space for their weekly in-person summer meetings starting in July. In the off-season, Bush said, they meet virtually. Going forward, the building will be available to the community for rentals too. 

“We envision it would be a great space for a wedding reception; a pop-up event; a meeting space for a retreat,” Bush said. “We’re looking into all kinds of possibilities.”

Each Cottager is asked to join at least two committees. Those subgroups plan activities for children (the children’s initiative committee), organize the group’s scholarship fund (community outreach and charity committee), oversee the maintenance of Cottagers’ Corner (Cottagers house improvement committee), and generally keep the group embedded in Island affairs, which was what attracted Bush in the first place.  

Bush, who was living in Boston at the time, became a Cottager in 2011. She joined at the urging of one of her Oak Bluffs neighbors who was active in the group; that neighbor became her sponsor. “When I first joined it was to give back to the Island, but it was also a way to join a community on the Island,” she said.

Through her involvement, Bush has connected with a mix of working professionals and retirees. The youngest active member of the group is thirty-four, while the oldest is ninety. Bush has also been connected to a legacy that spans generations and decades.

“One of the beautiful things about the Cottagers is that we have third-generation Cottagers, and then you have people like me,” Bush added. “Diversity of experience creates the best outcomes.”

Indeed, some women in the organization today can trace their families back to those early overcrowded porch meetings.

Mildred “Millie” Finley was an early Cottager. She arrived in Oak Bluffs in 1955 when she and her husband, Ewell Finley (known as E.W.), vacationed with another Black family. Before the end of that summer, the family of five purchased a home on Pequot Avenue, which became a sanctuary for four generations of Finleys.

“When Cottagers was beginning, my grandmother was trying to recruit everybody,” said Kharma I. Finley-Wallace, Mildred’s granddaughter. “She was very dedicated to her Cottagers. Very into the fashion shows, because she was a bit of a diva. That generation – they were all about doing well while looking good.”

Finley-Wallace, from Lake View, Long Island, grew up steeped in Cottagers business between her grandmother and her aunt, the Reverend Deborah Finley-Jackson, who had served as treasurer. Finley-Wallace joined the group in her twenties while her aunt was still active.

She was eager to bring the group into the twenty-first century with a website, but that idea was soundly rejected in the mid-1990s. (The group did agree to a website a few years later.) And while she attended meetings and taught art classes at Cottagers’ Corner, Finley-Wallace realized after a couple of years that maybe this wasn’t for her, after all. At least not yet.

“No one near my age was a Cottager,” she recalled. “All my aunties were [members], and my second grandmothers. I wanted to be a part of that, but then I found out…I wasn’t ready.”

Millie Henderson, a family friend from the same town in Long Island, who was also a Cottager, advised Finley-Wallace to “come back when you’re fifty.”

That turned out to be good advice.

After decades as a summer resident, Finley-Wallace moved her family to Oak Bluffs full-time in 2020. She rejoined the Cottagers and chaired the group’s annual Sunset Soiree fundraiser for the past three years. 

“I’m an event planner, so I was able to bring my professional life” to the group, Finley-Wallace said. In that time, she created a concert including a harpist, a casino-themed afternoon, and a formal dinner, all held at Featherstone Center for the Arts in Oak Bluffs. 

As annual events go, the fashion shows adored by Mildred Finley have gone by the wayside, along with the summer dances for teenagers. The Sunset Soiree will also take a break this year. But an always-popular walkthrough of some of the most interesting houses in Oak Bluffs remains. The group has hosted the annual house tour for thirty-nine years, and the fundraiser is a favorite of Bush’s. This year, it will take place on July 16.

“I love looking at the houses and getting ideas,” Bush said, noting the variety of homes that participate each season. “They’re all interesting houses. The imagination and creativity of the homeowners is just awesome.”  

And in honor of their seventieth anniversary, on July 30 the Cottagers will host a benefit concert at the Strand Theatre in Oak Bluffs with the legendary R&B singer Jeffrey Osborne. Tickets for all of the fundraising events, including a special $70 raffle, can be found on the Cottagers’ website. The grand prize for the raffle is a trip to the Caribbean island of Nevis.

Will there be a fourth generation of Cottager Finleys? Finley-Wallace is a mother to three sons, but there are female cousins to recruit, and maybe one day her granddaughter. (She is only five, so there’s time.)

“My sister has no interest,” Finley-Wallace said. “But you never know; she’s in her forties,” she added with a laugh.

After seventy years of service, the Cottagers have become part of the fabric of Oak Bluffs, gaining both Island and national recognition. The group has been acknowledged with exhibits at the Martha’s Vineyard Museum in Vineyard Haven and the Smithsonian National Museum of African American History & Culture in Washington, D.C., and Cottagers’ Corner has its own plaque as part of The Martha’s Vineyard African-American Heritage Trail.

“This is a group of women who wanted to have a legacy of giving back to the community,” said Cole, the community outreach chairwoman. “When I first joined, my sponsor told me, ‘You will meet Cottager women who will be friends for life.’ And it was true.”

“What I want to stress is how phenomenal and talented the Cottagers women are,” Bush said. “They are so skilled and so generous with their skills and their time. It’s an honor to be president as we start the next seventy years.”

There will be more house tours, more food drives, more fundraisers, more scholarships. And always more sisterhood, which is what makes it all worthwhile.

“What brings me joy about it is feeling a connection to the Black community,” Finley-Wallace said. “We’re an organization of one hundred women. We may have drama. But at the core of us, we will show up. And I love that about Cottagers. We all understand that we have a short period of time for what good we can do. I don’t know anyone there who’s there for status. We are so intent on giving back to this Island.”