The African American Heritage Trail of Martha’s Vineyard began as part of a promise to a little boy, and in 1998 the Shearer Cottage was dedicated as the first site on the Trail. The ambition was to reach a total of eight sites. That there were many stories was obvious, but the depth and range of the experiences that make up the tapestry of the African American experience on Martha’s Vineyard was amazing. From fugitive preachers to nationally known politicians, all the struggles and triumphs of people of color were part of the story of this Island.

Editor’s Note: Olive Tomlinson spoke with Linsey Lee, oral history curator for the Martha’s Vineyard Museum, about her recollections of Liz White’s Shearer Summer Theatre, one of the first summer theatre groups on the Island after World War II. An actress who felt stymied by the stereotyped African American roles available to her on Broadway, in the summers Liz returned to Oak Bluffs where her family owned and operated Shearer Cottage, a popular inn for vacationing African Americans.

Henry Louis (Skip) Gates Jr. is passionate about roots. The Harvard professor, writer and genealogist first started on a family tree as a nine-year-old, after his grandfather’s burial, wanting to know about his connection to his father and grandfather. He’s followed his passion in his professional life, through scholarship and his popular television shows tracing people’s genealogy, and in the personal realm: still working on the family tree, he is trying to find the identity of his great-great-grandfather.

The Highlands, as they are familiarly known, are located on East Chop, the general boundary being laid out like the Methodist Camp Ground in Oak Bluffs, with a central circle ringed by house lots along curving avenues.

It’s past time for Americans to have a conversation about race, a panel of cultural and academic luminaries agreed at a crowded Martha’s Vineyard Performing Arts Center on Wednesday. What the rules of that conversation are, who the participants are and where the conversation will take place is less certain.

The spirit of community, fellowship and Vineyard charms permeate the walls of the five houses being presented by the Cottagers for the 28th annual Cottager House Tour on July 21. The houses represent a diverse group in style and age. Some remain similar to the original houses built around the middle of the 19th century, others are the newly built or refurbished homes of today with current amenities. The owners love their houses passionately and are engaged in the community around them. The names on some houses reflect the owners’ love of the Vineyard.