By 7:30 on summer mornings, while some vacationers are still deciding what to do with their day, swimmers are already in the water of Oak Bluffs, Massachusetts. Some have been coming for decades. Others are joining for the first time. Together, they exercise, socialize, and welcome another day at Inkwell Beach, a small stretch of Martha’s Vineyard shoreline where Black Americans have gathered for generations.
Known as the Polar Bears, the group began gathering in 1946, when nine Black summer workers started swimming before their shifts. Eight decades later, the ritual continues. The Martha’s Vineyard Times documented the group’s 80-year history in June 2026, tracing how an informal gathering of friends became a tradition built on movement, fellowship, and connection.
The appeal of the Inkwell is, in many ways, wonderfully ordinary. People come to swim, catch up with friends, and spend summer days with family. But behind those familiar pleasures is the history of a community that made room for Black people to enjoy them.
Source: Courtesy of Netflix / Courtesy of Netflix
If Netflix’s Forever sent you to Google wondering where Keisha and Justin had gone when the Netflix series traded Los Angeles for Martha’s Vineyard, you probably weren’t alone. The fifth episode of Mara Brock Akil’s coming-of-age romance introduced viewers to the island’s Black summer traditions. Bravo’s Summer House: Martha’s Vineyard, which premiered in 2023, had already followed a group of young Black professionals vacationing there.
My own introduction came through the 1994 film The Inkwell, starring Larenz Tate. Set in 1976, the movie follows a teenager navigating family life, first love, and adolescence during a Vineyard summer. I remember being fascinated by a world where Black families could spend an entire vacation concerning themselves with crushes, family disagreements, and what to do after leaving the beach.
The movie was a fictional introduction to a real cultural inheritance. What I didn’t know then was how many people had worked to make those summers possible. The history of the Inkwell reaches beyond a vacation destination associated with wealthy Black families. It is a story of entrepreneurship, community, and traditions deliberately carried forward.
Before the Vineyard became a summer destination, it was home to Indigenous people. The Wampanoag Tribe of Gay Head (Aquinnah) traces its ancestors’ presence on Noepe, the Wampanoag name for the island, back at least 10,000 years. Black people also have a centuries-long history there, arriving through enslavement, maritime work, domestic labor, and other routes. In the decades after the Civil War, Oak Bluffs became a summer destination for African Americans from Boston, New York, Washington, D.C., and elsewhere.
Segregation shaped where Black Americans could travel, find lodging, and enjoy the outdoors. The National Park Service’s research on African American outdoor recreation documents how exclusion from beaches, parks, resorts, and other leisure spaces led Black communities to establish recreational spaces of their own. A vacation did not automatically mean relief from the racial restrictions of everyday life.
Oak Bluffs offered opportunities that many destinations did not, even though discrimination persisted there, too. Black visitors found ways to open businesses, build relationships, and establish a community they could return to each summer. That sense of welcome took work.
Among the people doing that work were Charles and Henrietta Shearer, whose family helped expand Black access to the island. Charles, born in Virginia in 1854 to an enslaved woman and a white farm owner, attended Hampton Institute, now Hampton University, and became an educator. Henrietta was also a teacher and later ran a successful laundry business. After first visiting Martha’s Vineyard in 1895, the couple acquired property in Oak Bluffs. In 1912, they established Shearer Cottage, a 12-room inn for Black travelers who could not count on being welcomed elsewhere.
According to the National Trust for Historic Preservation, Shearer Cottage became so popular that its owners sometimes found rooms for guests in neighboring homes. Communal meals brought more than 50 people together, and the guest list included Madame C.J. Walker, Paul Robeson, Ethel Waters, and Lillian Evanti. A young Adam Clayton Powell Jr. also spent summers there. Beyond lodging, the inn fostered the relationships that helped make Oak Bluffs feel like a community.
The famous names tell only part of that story. Workers, educators, entrepreneurs, and families of different means shaped the island’s Black social life. Guesthouses and other local businesses made visits possible for people who otherwise might have had nowhere to stay.
On Lower Circuit Avenue, Georgia O’Brien and Louisa Izett operated Aunt Georgia’s House. According to the African American Heritage Trail of Martha’s Vineyard, Black travelers could secure room and board there for about $7 a week in its early years. Places like Aunt Georgia’s House and Shearer Cottage helped turn individual vacations into an enduring community. Someone had to welcome the visitors, feed them, and give them a reason to come back.
As the community grew, a section of Oak Bluffs Town Beach became closely associated with its Black summer residents. The origin of the nickname ‘Inkwell’ remains disputed. Some accounts describe a derogatory label used by white residents, while others connect it to the area’s Black literary figures. In a 2017 essay for Martha’s Vineyard Magazine, culinary historian and longtime Vineyard summer resident Jessica B. Harris remembered the name as an affectionate inside joke among beachgoers before it entered wider use. However the name began, Black beachgoers made it their own. Harris remembered a childhood when access to other beaches could be more restrictive. She wrote, ‘the town beach was free and it was ours!’ The beach offered a setting where Black visitors could reconnect with one another and where their children could grow up within relationships established long before they were born.
For Skip Finley, childhood summers at the Inkwell came with a schedule. By 10 a.m., he was on the beach, and by 6 p.m., he was expected home. In between were bicycles to ride, blueberries to pick, summer jobs to work, and girls to meet. He knew his way around Oak Bluffs and the people who made it feel familiar.
In a 2018 conversation with The Vineyard Gazette, Finley joined longtime residents Olive Tomlinson and Gretchen Tucker Underwood to remember growing up on the island. Tucker Underwood described dropping in on friends without formal invitations and the inventive ways girls protected their hair in the water. They wore inverted sailor caps decorated with names, sometimes including those of boyfriends.
Source: MediaNews Group/Boston Herald via Getty Images / Getty
Tomlinson remembered birthday celebrations in author Dorothy West‘s backyard and a network of adults who watched out for one another’s children. The result was a freedom that many young people remember as vividly as the water itself: a whole community in which to explore, socialize, and grow up.
In her 2017 essay for Martha’s Vineyard Magazine, Harris described how the beach changed over the course of a day. By midday, families had arrived with chairs, umbrellas, and coolers. Mothers played cards and caught up with friends while children swam. Familiar spots along the sand became places to greet whoever passed by, often without making any plans at all.
Harris remembered Lois Lippman, a regular whose presence was so familiar that Harris thought a section of the beach ought to bear her name. Lippman spent decades returning to the same spot, greeting friends and enjoying the sun. Her ritual illustrates what made the Inkwell special: people didn’t need an itinerary when the company was the attraction.
The shoreline also became a backdrop for weddings, memorial services, and other milestones. Harris remembered gatherings that marked both joyful beginnings and painful goodbyes. As children became parents and elders passed on, the beach accumulated the stories of people who had shared their summers there.
More Than A Place To Rest
The Inkwell’s social life also made room for grief and collective reflection. When events beyond Martha’s Vineyard shook Black communities, people could come together on the same shoreline where they spent their summers celebrating.
In August 2017, after deadly white supremacist violence in Charlottesville, Virginia, members of the Inkwell Polar Bears, the Martha’s Vineyard NAACP, and other residents gathered for a vigil. Charlayne Hunter-Gault, writing for The New Yorker, described participants joining hands, praying for racial harmony, and singing ‘We Shall Overcome.’ The gathering followed earlier observances, including a memorial for civil rights leader Julian Bond and a vigil in response to violence in Dallas.
Those gatherings reveal another side of the Inkwell. A summer away from the mainland did not erase the events that weighed on people back home. The bonds formed through years of shared recreation gave residents and visitors a place to mourn, reflect, and respond together.
That connection between community and political consciousness also appears in another tradition associated with the beach: public readings of Frederick Douglass’ 1852 speech, ‘What to the Slave Is the Fourth of July?’ The readings grew out of a rain-interrupted holiday picnic in Oak Bluffs in 1998. Author and playwright Abigail McGrath helped turn the impromptu gathering into an annual event in 1999, and it eventually moved to the Inkwell.
In 2023, The Vineyard Gazette reported that more than 40 volunteers took part, reading Douglass’ indictment of a nation celebrating freedom while millions were enslaved. Documentary filmmaker Stanley Nelson Jr. was among those discussing the contradictions in America’s founding ideals. Hearing those words at the Inkwell gives the beach’s history another dimension: this was a place where people could enjoy freedom while reckoning with its unfinished promises.
Today, social media can make Black rest look like a new discovery, complete with a carefully arranged beach chair and a caption about the soft life. The families who made memories at the Inkwell needed no such language. They understood that swimming, playing cards, enjoying friends, and doing absolutely nothing could be worthwhile in their own right. That history is especially important as the Vineyard attracts new audiences. Television and vacation videos can show visitors where to go, but they cannot fully explain what made a stretch of sand feel like home to people who returned for decades. Those meanings survive in family stories and the memories of longtime beachgoers.
Preserving the Inkwell’s legacy also means remembering the people whose names will never appear on a historical marker, including the parents who packed for another summer, the friends who claimed familiar spots on the sand, and the elders who watched one generation grow up before welcoming the next. They are as much a part of the beach’s history as its most famous visitors. For those discovering the Inkwell today, there is room to make new memories without overlooking the old ones. The generations who gave this beach its place in Black culture were not always trying to make history. They were living their lives, enjoying their summers, and finding reasons to return. In doing so, they created something lasting.
