The Martha's Vineyard African American Heritage Trail

Jen O'Hanlon, REALTOR®


Exploring the African American Heritage Trail: A Journey with The O'Hanlon Group

Welcoming February with a Journey of Discovery

As Black History Month approaches, we at The O'Hanlon Group are excited to embark on an educational and inspirational journey through the African American Heritage Trail of Martha’s Vineyard. This exploration is not just a trip; it's an opportunity to connect with a significant part of the island's history. We plan to share our experiences and discoveries with you, our valued friends and clients, through our weekly newsletter and social media content. 

The Significance of the African American Heritage Trail

The African American Heritage Trail, established in 1998, is a testament to the enduring legacy and contributions of African Americans on Martha's Vineyard. The trail comprises over 30 sites, each symbolizing a unique story of African American history and culture. From Menemsha, where slaves found a path to freedom aided by the Wampanoag Tribe, to the home of Dorothy West, a notable figure of the Harlem Renaissance, every site has a tale to tell.

Key Stops on Our Trail

During our tour, we'll visit several pivotal locations:

  1. Menemsha: This quaint fishing village was an historic escape route for slaves, marking a crucial chapter in the pursuit of freedom.

  2. Great Rock Bight: William A. Martin's great-grandmother, Rebecca Martin was born in West Africa and was enslaved in Chilmark. She died a free woman in 1801.
  3. William A. Martin’s Homestead: Celebrating the life of the island’s only African American whaling captain, this site epitomizes resilience and achievement against the odds.

  4. Pulpit Rock: The site where preacher John Saunders spread the gospel, playing a significant role in the religious life of Martha's Vineyard's African American community.

  5. Shearer Cottage: Originally a laundromat, it later became a pioneering Black-owned guest house, signifying progress and enterprise. The photo below shows the Shearer family gathered on the cottage porch in 1931; Charles Shearer stands third from the right.

The Shearer family gathered on the cottage porch in 1931

       6. The Home of Dorothy West: Celebrating the life of an influential writer of the Harlem Renaissance, her home embodies the cultural and literary contributions of African Americans to the island. If you haven't         read any of her books, consider her last novel, The Wedding. Set on the Vineyard in the 1950s, it tells the story of life in the Oval, a proud, insular community made up of the best and brightest of the East                     Coast's black bourgeoisie.

Sharing Our Experience

As we traverse the trail, we’ll delve into the stories and legacies that these sites preserve. Our aim is to not only educate ourselves but also to bring these narratives to our audience, enriching our collective understanding of the island's diverse history.

We look forward to sharing detailed insights, personal reflections, and photographs from our journey. Each newsletter and social media post will highlight a different aspect of the trail, bringing to life the rich heritage and profound contributions of African Americans to Martha's Vineyard.

Join Us Virtually

While we explore these historic sites, we invite you to join us virtually. Follow our journey on social media and through our newsletter for weekly updates, stories, and more. Your engagement and feedback will make this experience even more rewarding.

Join Us In Person

We will be heading out each week in February on Thursdays, from 10:00am-12:00n and would love for you to join us! Call Jen at 508-212-8278 for more information.


Our journey through the African American Heritage Trail is more than just a tour; it's a step towards greater understanding and appreciation of the African American community's significant role in shaping Martha’s Vineyard. We look forward to sharing this enlightening experience with you​​​​​​.


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