Our social media feeds have been filled with Black travelers living it up on Martha’s Vineyard, specifically Oak Bluffs, these last few weeks. Or, you’ve likely heard friends and family talk about the annual ‘Black August’ that happens on the popular Massachusetts island. 

But, what draws us to this town year after year? 

While Martha’s Vineyard overall is still heavily populated by mostly white residents, Oak Bluffs comes alive each summer as thousands of Black people descend upon the town for annual meetups, events and to simply take up space in a place that hasn’t always wanted us there. It has even served as a source of inspiration for Black historical greats like Maya Angelou, actor Paul Roberson and more. 

In 1912, Charles Shearer—the son of an enslaved woman and an enslaver—opened the first Black inn in the Oak Bluffs neighborhood. This was a time when discrimination and racial segregation ran rampant across the United States, and Black travelers had limited options on safe places they could stay overnight during vacation. Shearer Inn became the go-to summer haven for middle and upper class Black families, as the Harlem Renaissance and other Black economic booms took place. Year after year, the area would be filled with the Black elite, business owners and more as they traveled to Inkwell Beach, aka "The Inkwell," for their own version of fun in the sun—a true display of Black joy personified.

The historic, Black-owned Oak Bluffs Inn. Image: Instagram/@oakbluffsinn.

The meaning behind the name, The Inkwell, however is still up for debate. Some say it was nicknamed by Black visitors who would look down on the beach from nearby sidewalks, and see the water filled with Black people, thus creating the appearance of an inkwell. Others say it was once a derogatory term created by white residents and visitors for similar reasons and as a way to segregate the beach from others in the area. But was later adopted and embraced by Black visitors— thus turning a negative into a positive. 

As the years went on, Black people continued to seek refuge and even find community during summers in Oak Bluffs. So much so, that in the late 1940s, visiting swimmers started a morning ritual known as the Oak Bluffs Inkwell Polar Bears. This daily swim circle—which still takes place present day—is a time for fellowship, but also a moment to simply be free within the waters. Stronger swimmers would use the time to warm up their bodies before heading out on a longer swim, while those who weren’t as strong would stay behind in the more shallow parts to frolic.

Polar Bears meet for morning swim. Image: Facebook/Martha's Vineyard Oak Bluffs "Inkwell" Polar Bears.

August, specifically, became the more popular month for Black visitors in recent years, in large part to the long-running Martha’s Vineyard African American Film Festival. 2022 marked the 20th anniversary of the event, which celebrates and honors Black film and television greats of the past and present. Typically held in early to mid-August, the event welcomes not only celebrities, screenwriters and producers—but also Black businesses and brands that come to showcase their latest products and merchandise. It’s the epitome of Black excellence. 

The popularity of Black August continues to grow each year, whether for those wanting to attend the film festival and secondary events, or to simply be around beautiful Black people in a beautiful destination. And despite the glitz and glamour of Black August, the message is still very clear: Oak Bluffs is our safe place and no one can ever take that away from us.