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.

Since 1968, the black middle class in America has quadrupled, Henry Louis (Skip) Gates told a packed house at the Edgartown Whaling Church on Thursday evening.

But that was the only positive news in an otherwise bleak survey of the state of black education by a panel of experts convened by Professor Gates and the W.E.B. Du Bois Institute for African and African American Research.

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.

My grandfather, Charles Shearer, was born into slavery. Henrietta Shearer was of Native American and African American descent. They were both educated at Hampton University.

Nodding to Professor Henry Louis (Skip) Gates Jr. at his Whaling Church panel discussion Achieving Equality in the Age of Obama last night, Princeton professor Melissa Harris-Lacewell shook her head and said: ”If you had told me this time last year, when we were all pretty emotionally up and excited, even though George W. Bush was still our President, that we would actually feel worse a year later, when Barack Obama was our President, about questions of race in America, I would have told you you were lying.”

But as he enters, he bellows with a theatrical gesture of his walking cane in the direction of his friend and legal counsel, Charles J. Ogletree Jr., the man he calls Tree.