The Best Time To Visit Martha’s Vineyard Is In August (And A Week In July!)

By   |   August 25, 2022   |   Travel

What’s the best time to visit Martha’s Vineyard? Many repeat visitors would declare it’s during the eventful month of August. But for those taking part in “Legacy Week on the Vineyard,” it’s the last week of July.

Legacy Week on the Vineyard

“Everyone wants to highlight their school or Greek organization and showcase their love for them,” declares Sheryl Wesley, Legacy Week on the Vineyard‘s founder and CEO. The organization has welcomed HBCU graduates and Divine Nine visitors to the Vineyard for a week-long explosion of events since 2016. “This is an opportunity to relax, recharge and reconnect amongst us.” This year’s events included the Eats & Beats Brunch honoring Howard University alumni.

Martha’s Vineyard African-American Film Festival

#CIROCStands for Black Businesses Panel Discussion with Regina Hall and Angela Yee at Martha's Vineyard African American Film Festival

At the beginning of August, CÎROC partnered with Martha’s Vineyard African-American Film Festival to celebrate the rich roots of excellence that run deep in the island.

Actress Regina Hall and media personality Angela Yee joined local Black-owned Martha’s Vineyard business owners like Nya Clarke, owner of Martha’s Vineyard Island-Wide Realty, Zita Cousens, owner of Cousen Rose Gallery, the longest-running gallery on the island and India Rose, owner of Sideline, a motivational sportswear and streetwear brand, to share their inspirational journies to success.

Get Around With Martha’s Vineyard Black-Owned Business Directory

Sideline owner Rose is also the Founder of Martha’s Vineyard Black-Owned Business Directory. She created the directory as a digital listing after fielding many inquiries from Black vacationers looking for Black-owned businesses and resources. In 2021 the directory became a printed booklet, and in 2022 the booklet, which is available for purchase, doubled in size.

I couldn’t be more excited about the impact that the Directory is having on the Island community,” Rose shares with DGD. “Local Black-owned businesses are thriving and business owners reach out to me regularly to attribute an increase of business to the Directory. I couldn’t be happier to see how this resource is also changing how people vacation. People are now using this guide as a way to help plan their Vineyard vacations and I am thrilled about that.”

The Inn at Shearer Cottage: A Hotel With History

Shearer Cottage

The Inn At Shearer Cottage was one of the first establishments to provide lodging to middle-class Blacks visiting from Boston, New York City and Philadelphia. In 1903, Charles Shearer and his wife Henrietta purchased a second property in Oak Bluffs which overlooked Baptist Temple Park. Henrietta initially managed a laundry business on the property. In 1912 the home became Shearer Cottage, a summer inn that catered to a devoted population. The inn was a place to rest and enjoy communal meals in the cottage dining room, which were prepared by Shearer family members.

Earlier this year, The Inn at Shearer Cottage announced a proposed renovation and expansion. It will welcome guests again in summer 2023, with a goal to service visitors for “the next 100 years.”

The African-American Heritage Trail: Remembering Our History

Bunny Cottage

Much of Martha Vineyard’s Black history has been recognized by The African-American Heritage Trail of Martha’s Vineyard, a nonprofit organization devoted to marking “previously unrecognized contributions made by people of African heritage,” on the island.

Identifiable by commemorative bronze plaques dotted throughout the region, the tour includes such iconic spots as “Bunny Cottage,” which Adam Clayton Powell, the first African American congressman from  New York and the Northeast, purchased in 1937; Harlem Renaissance writer Dorothy West‘s former home in the Highlands of Oak Bluffs, and “Villa Rosa, The Overton House,” a grand Victorian mansion in Oak Bluffs that served as a summer headquarters for the Civil Rights movement. Dr. Martin Luther King Jr. was a frequent visitor.

Several people who contributed to the growth of areas like Oak Bluffs, Edgartown, and Tinsbury are also commemorated on the trail.

photo credits: So Focused Photography, Shearer Inn, Seacoast Properties

Filed Under: Travel
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