Black History MV: The African American Heritage Trail of Martha’s Vineyard Adds Two New Sites

The African American Heritage Trail of Martha’s Vineyard added two new sites in 2021, bringing the current total to 33. Each site is dedicated to bringing to light a contribution made by people of African descent on the Island. And it’s part of our spotlight this month Black History MV: The African American Heritage Trail of Martha’s Vineyard Adds Two New Sites

The Mission of the Trail is to continue to research and publish previously undocumented history and to involve the Island community in the identification and celebration of the contributions made by people of color to the island of Martha’s Vineyard. In pursuit of that goal, we have identified and celebrates sites in every town on Martha’s Vineyard”. 

Black History MV: African American American Heritage Trail co-founders Dr. Elaine Cawley Weintraub and Carrie Tankard Villa Rosa House Oak Bluffs
Carrie Tankard + Dr. Elaine Cawley Weintraub in front of Villa Rosa, Site # 17

Founded by Dr. Elaine Cawley Weintraub and Carrie Tankard who met in 1989, they realized they had a shared vision. Both women wanted to educate people on the history of people of color in the schools of the Island. And so their research began and it continues to this day, helping make the history taught inside and outside the classroom more inclusive.

Many of the locations on the Trail may be familiar, Grace Church, the Shearer Cottage, Cottagers Corner, and Villa Rosa – the Overton House. We joined the two founders for our own tour, in a recent Vineyard Bucket List video.

However, there are many sites that are less known to discover that are rich with history, including the two newest, Esther’s Story, and the Nameless Trail.

Black History MV: The African American Heritage Trail of Martha’s Vineyard Adds Two New Sites – Esther’s Story

In 1743, the sloop Endeavor docked in Edgartown Harbor for the evening on its journey heading to the South. Onboard was an enslaved woman of African and native heritage, Esther. She was a fugitive, captured in Boston, who was being brought back to the South to face the consequences of her escaping from enslavement.

Though her hands were bound and her feet tied to a crowbar, she somehow managed to escape in the night aboard the sloop’s longboat, never to be seen again. Did a member of the Endeavor’s crew assist her? Did she free herself? It is a 277-year-old mystery.

Black History MV: African American American Heritage Trail Esther Memorial Wharf Edgartown
Esther | Memorial Wharf

What is not a mystery is this woman’s strength and determination to be free. She refused to go back to an enslaved life in the South. We don’t know how, but she remained free. Esther embodies the human spirit, the ability to risk everything to be free.

It is this story that will live on, a story to inspire. A story that is now shared with all those who visit Memorial Wharf to take in the view or to fish. Knowing that you where history happened makes an impact. When you read Esther’s plaque, you cannot help but wonder how she did it, how she escaped. She did it, and left a mystery in her wake.

Adding this site, number 33, was a dream come true for Elaine, 15 years in the making. Elaine discovered Esther’s story through archival research. She traced her through a deposition on record and references to her case made in an 1850s edition of the Vineyard Gazette. In the summer of 2021, because of this work, the inspirational story of Esther was shared not only with the community but the world.

In addition to this site being on The African American Heritage Trail of Martha’s Vineyard, Esther’s story has been recognized as part of the  National Underground Railroad Network to Freedom. The only location currently located on Martha’s Vineyard.

Esther Dedication Video | The African American Heritage Trail

Black History MV: The African American Heritage Trail of Martha’s Vineyard Adds Two New Sites – The Nameless Trail

In addition to Esther’s site, last Summer, #32, the Nameless Trail was added. On May 20th, 2021, at the Martha’s Vineyard Public Charter School, students unveiled the plaque at the school. This plaque honors those who lost their names because of the cruelty of slavery.

Black History MV: African American American Heritage Trail The Nameless Trail West Tisbury Martha's Vineyard Public Charter School
The Nameless Trail | Elaine Weintraub

Elaine worked with the Charter School students to help them learn the history of what it was like to be a slave and what people had to face — including not even being valued enough to be given a name, but rather a value. Having your given name taken away, receiving a new name or none at all. I cannot even find the words to describe the depravity people had to endure as a slave.

Black History MV: African American American Heritage Trail The Nameless Trail West Tisbury Martha's Vineyard Public Charter School
Martha’s Vineyard Public Charter School Nameless Trail Dedication | PC: Elaine Weintraub

The children felt it was important to honor those people not given names or those who lost their names, to remember them. Their names live on, honored here. The picture above was taken when site #32, The Nameless Trail, was commemorated. For more about the work Elaine did with the MVPCS children, you can read book two in the three-book series A Good Name is Worth More than Silver or Gold.  

Black History MV: African American American Heritage Trail

Black History MV: The African American Heritage Trail

Black History MV: African American American Heritage Trail Villa Rosa House Oak Bluffs the Overton House
Villa Rosa – the Overton House #17 | Oak Bluffs

You can follow African American Heritage Trail on your own with a map. But to fully experience the rich history and community context, there’s nothing like the narrative and storytelling, that the excellent Heritage Trail guides provide.

Black History MV: African American American Heritage Trail Oak Bluffs Emma Maitland Chambers
Emma Maitland Chambers #26 | Dukes County Avenue, Oak Bluffs

Tours are scheduled regularly throughout the summer season but available other times as well. Check The African American Heritage Trail of Martha’s Vineyard website for details. You can also find the African American Heritage Trail on Facebook. You can also learn more with our Vineyard Bucket List Series – Martha’s Vineyard Bucket List: African American Heritage Trail Of Martha’s Vineyard.

An Island Wide Experience

When Elaine and Carrie first founded the trail in the 90’s, they envisioned four sites. Now there are 33, all across the island. You will find sites in West Tisbury, Chilmark, Vineyard Haven, Aquinnah, Menemsha, Edgartown, Chappaquiddick Island, and Oak Bluffs.

Black History MV: African American American Heritage Trail Landladies of Oak Bluffs Martha's Vineyard
The bench across the street from Landladies of Oak Bluffs, Site #16

Writing this series about Black History on Martha’s Vineyard has been educational, and it is amazing how much history can be found on the shores of this special Island. If you want to learn more, we encourage you to explore Black History on Martha’s Vineyard not only with The Martha’s Vineyard African American Heritage Trail, but also at the Martha’s Vineyard Museum, and by reading books by authors like Skip Finley and Tom Dresser.

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