The Henrys’ dream

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Black History Month was created to focus attention on the extraordinary contributions of African Americans in the U.S. In honor of this initiative, this February edition of “Voices bySharisse” highlights the extraordinary story of the Henry family and their historic home, Dragonfly House in Oak Bluffs, which will be officially recognized as a stop on the African American Heritage Trail this spring. 

OAK BLUFFS: I met Danroy (Dan) and Angella Henry during my first summer job here on the Vineyard, waitressing at the Barn, Bowl and Bistro. From the moment I greeted them at their table, I sensed a special aura surrounding them, and immediately was drawn to their positive energy and uplifting presence. It didn’t take long for them to become cherished regulars, and for us to begin diving into purposeful conversations.

Both Dan and Angella could sit at any table. Their achievements, honors, contributions, and public recognition supersede most. With his successful career in human resources and her impactful role in advocacy, together they are a true power couple.

Their careers have made them influential, but their ability to turn grief into action and tragedy into triumph has made them the epitome of community activism and excellence. From the outside looking in, one would not see the pain and suffering the couple has endured since the tragic killing of their son. On Oct. 17, 2010, at the age of 20, DJ had his life tragically cut short. A 20-year-old Easton native, Danroy “DJ” Henry was a talented athlete and a brilliant student at Pace University in Pleasantville, N.Y., where he was playing football. After a homecoming game which his parents had come to attend, he was with friends at a restaurant and club when the police came in and broke up the evening. He was trying to exit the parking lot on police instruction when an officer stopped his vehicle and jumped on the hood of the car. He was shot and killed by a white police officer who never faced charges. In the aftermath of the George Floyd shooting, there were renewed calls for the Justice Department to assign federal investigators to take a deeper look. After a two-year review, the Westchester District Attorney ruled in 2023 that there was not sufficient new evidence to warrant bringing the case to a new grand jury.

After the loss of their son, the couple channeled their rage and intense grief into meaningful advocacy, honoring his legacy by founding the DJ Henry Dream Fund Foundation.

DJ Henry Jr., the Henrys’ first son, was an avid reader who since childhood was known for his altruistic and gentle nature. DJ had a remarkable commitment to community betterment and dedication to helping others. DJ’s “yes, I can” mindset, with intense passion and drive, was a true reflection of the tight-knit family he grew up in. His legacy was channeling that exuberance both on and off the field, which not only propelled his athletic journey but characterized his life and legacy.

When I asked the Henrys what the driving force had been for them to instill philanthropic zeal in DJ at such a young age, Dan said, “Legacy is important. No matter what age you are, everything you do is a bit of a footprint in the sand. This defines your legacy even at a young age.” As stated on its website (djhenrydreamfund.org), the DJ Henry Dream Fund (DJHDF) is “set out to honor DJ’s legacy by helping kids in Massachusetts achieve their dreams. The vision of the DJ Henry Dream Fund is to share DJ’s love of sports by providing community-based scholarships to Massachusetts children between the ages of 5 and 18. Believing that every child deserves a ‘YES’ when it comes to community engagement, DJHDF provides financial support, allowing youths to participate in community-based programs such as sports, performing arts, and summer programs. Participation in such programs, despite economic position, empowers young people to be the best they can be.” Carrying DJ’s passions and legacy is what keeps the Henrys moving forward each and every day.

If you are looking to support the Henrys in their efforts to elevate humanity, you can contribute to the DJ Henry Dream Fund, but the couple also encourages you to participate in community service acts, and other small acts of kindness and generosity around the Island and beyond. For example, one yearly tradition the family maintains on the Vineyard is doing beach cleanups in DJ’s memory — and they encourage Islanders to volunteer to participate.

In continuous pursuit of their purpose to make a positive impact on the world, the Henrys founded Dragonfly MV Properties in 2017. Its mission is to “provide the platform for curating experiences while creating Martha’s Vineyard vacation memories.”

One of their Dragonfly properties is Dragonfly House. This home is on the corner of Canonicus and Seaview avenues in Oak Bluffs, overlooking Inkwell Beach. This home was just the peaceful sanctuary the couple was looking for to help make the next chapter of their lives more endurable. When undergoing any life-changing process, many people look for signs to interpret as an indication from the universe signifying confirmation about the situation you are going through. For the Henrys, this sign came in the form of dragonflies — dozens swirling around them as they sat on the bench dedicated to their son in Ocean Park, right after they had toured the home. They decided to name the house after the dragonfly. Dragonfly MV Properties’ website states, “For over 2,000 million years, dragonflies have flown the earth, as reminders of our own need to transform. They help us to reflect during hardships and prosperity. They remind us of the need to take time to rejuvenate, reflect, and rest.”

The Henrys raised DJ and his siblings in an intimate and loving environment, one supported by the Vineyard’s closely connected community — especially the African American families in Oak Bluffs. This is the kind of environment that fosters such a strong sense of belonging and camaraderie, with active participation in something bigger than yourself, in pursuit of collective well-being. The Henrys were pleased to learn that the grounds of the home were inhabited by protective spirits of our ancestors; another clear indication the Henrys are exactly where they are supposed to be.

Before the Henrys, Dragonfly House was operated as Eastman’s by the Sea from the early 1950s through mid-1990s. This home was the first house in Oak Bluffs on the waterfront listed in “The Negro Motorist Green Book.” The “Green Book” was a travel guide published during the late Jim Crow era, from 1936 to 1966, as a way to help Black travelers navigate safely. Eastman’s was operated for many years, and is likely one of the longest-running businesses that welcomed Black travelers during this time. The couple even have a copy of the original guestbook in the house!

Before there was Eastman’s by the Sea, First Lt. John Ritchie was the owner of the house. Ritchie was an American Union Army officer, traveler, and diarist in the Civil War. Due to his eyesight, Ritchie was not able to fight in the war as a soldier, so he shared the stories of Black soldiers instead. Ritchie’s diary, now at the National Museum of African American History and Culture in Washington, D.C., was the principal storytelling document of the Massachusetts 54th Infantry Regiment, of which he was a part.* You may be familiar with the movie “Glory,” which is based on this specific regiment. To think 90-plus years ago, this home was known as a safe space for people of color to congregate without harm, and it still serves as a space for camaraderie in our community to this day, is quite magical –– aligning perfectly with the history of the house.

This spring, Dragonfly House will be officially recognized as an entity on the African American Heritage Trail on Martha’s Vineyard. The African American Heritage Trail’s mission, according to its website, 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.”

Heritage Trail induction ceremonies are customarily attended by people directly involved or connected to the specific site. With community always at the forefront of their minds, the Henrys have invited people connected to the other 30-plus sites on the trail to be a part of their dedication ceremony. Sharing this milestone moment honors the spirit of the trail by actively engaging in thoughtful, intentional respect for not only our ancestors, but our collective body of African Americans on the Island as a whole. These measures are not just symbolic but a true testimony to the unwavering commitment to the preservation and empowerment of our Island community.

Be sure to follow up with Voices bySharisse in June for more information on Dragonfly House’s establishment in the African American Heritage Trail. 

* “John Ritchie’s diary was one of the records used to prepare the regimental history of the 54th: Luis F. Emilio, ‘A Brave Black Regiment: History of the Fifty-Fourth Regiment of Massachusetts Volunteer Infantry, 1863–1865’ (The Boston Book Co, 1894).” —As stated in “Emancipation Project, The Civil War Diaries of John Ritchie”