Black vacationers travel to Martha’s Vineyard (2024)

By Jason Lewis

The tiny Massachusetts island of Martha’s Vineyard has been a summer haven for Black travelers for over a century. Particularly during August, thousands of Black people visit the beach town Oak Bluffs for social events, aquatic and beach activities, and networking. The island features gingerbread cottages, lantern walks, hiking and biking trails, and the natural beauty of a coastal town.

This annual summer retreat for Black families dates back to 1912 when Charles Shearer, born to an enslaved woman, opened the first Black inn in Oak Bluffs. During that time period of segregation in the U.S., Black travelers had limited vacation options around the nation, so The Inn at Shearer Cottage became a very popular destination for the Black elite and middle class. For generations Black vacationers have bounced from the Inkwell Beach to day parties and wine tasting events, and then to fancy dinners. Porch parties go on all night long. Cruises or just hanging out on the beach are ways to leisurely pass through the day. This vacation has been a symbol of Black wealth.

In 2023, USC Black Alumni Association (UBAA) took their first trip to the island, and now they are making it an annual event.

“The island is a very unique experience,” said Jasmine Taylor, UBAA executive director. “It’s not like any vacation that I’ve ever had, and I’ve been to 40 countries. There’s nothing quite like Martha’s Vineyard in August, because it’s kind of like an island takeover of the most amazing Black people anywhere. When we were there, the candidate for U.S. Senate at the time, Hill Harper, was one of our special guests at our wine tasting event. He came to the wine tasting en route to a meeting that was happening at Spike Lee’s house with Michelle and Barack Obama, Kamala Harris, and other Black political leaders. We left that event and went to an event at a house that Google set up for the weekend. They were having a DEI (diversity, equity, and inclusion) conversation. So you have everything from summits and conferences to political leaders to actors because there is the African American Film Festival there. We were walking down the Circuit Avenue, which is the main street in Oak Bluffs, and we bump into D.L. Hugely and some of his friends.”

The allure of the historic Martha’s Vineyard Black experience is what attracts Black people from around the nation. There are several tours of the island, including the African-American Heritage Trail of Martha’s Vineyard.

“When we got there and we did the historic tour of Martha’s Vineyard, and we learned how much Black history is there, it just becomes that much more of a culturally relevant and impactful experience,” Taylor said.

During August, many travelers stay for the bulk of a week, with each week having different events.

“Week one and week four are sort of transition weeks, so they are quieter, but lots of people are there,” Taylor said. “Week two brings the African American Film Festival. We’ve built our activities into the second week. The third week is Black Greek week, amongst other things. The Inkwell becomes the “Pinkwell” when the AKAs take over it. There’s an incredible week of Delta events. I had the most beautiful experience with the Deltas. There’s a park where about 100 Deltas gathered in a circle and we met and fellowshipped. All of these women who I had never met before sang the sweetheart song and it was just beautiful. The energy from the D9 (Divine 9 Black fraternities and sororities), everybody is there. You see everybody in their letters the whole week. There’s a real vibrancy and culture to what’s happening in the month of August. And just to see that many Black people in one place, it’s just so fun.”

There is also a strong HBCU presence on the island. With the amount of college-educated and professional Black people in Oak Bluffs in August, there is a lot of networking and corporations sponsor several events. The Black Economic Alliance holds an annual gathering of policymakers, leaders, and innovators to discuss their efforts to advance Black work, wages, and wealth.

“There are a ton of affluent people, community leaders, business leaders, political leaders,” Taylor said. “They know that the Vineyard in August is a very unique opportunity, so a lot of corporations take advantage of that time to host different events, conferences, parties. You’re hopping from one thing to the next. There’s never nothing to do.”