Wally’s Cafe Jazz Club // 1947

Historically, the South End neighborhood of Boston was populated by middle- to upper-class white residents until the late 19th century, when financial crises paired with new, modern housing (constructed in the Back Bay West and Allston areas) shifted that population elsewhere. West Indian immigrants and Black Bostonians moved to the relatively new neighborhood and many formerly single-family homes were converted to tenements or multi-family uses. From this, a vibrant Black community flourished, bringing black-owned businesses like restaurants, banks and jazz clubs. The area’s famous jazz clubs boomed during the forties and fifties, yet, many have disappeared over the years with the gentrification and development in the neighborhood. Wally’s Cafe Jazz Club on Massachusetts Avenue, was founded by Joseph L. Walcott. Mr. Walcott “Wally” was a Barbadian who immigrated to America in 1910, eventually settling in Boston. He worked many jobs and eventually saved up enough by 1947, purchasing an old rowhome and converting the space into a club. Wally was believed to be the first African American to own a nightclub in New England. He brought famed jazz musicians to Boston, and they played at this iconic venue for decades until 1979, when the venue shifted across the street to this building. With the jazz movement waning in popularity, Wally maintained his commitment to the music by featuring young musicians who were attending prominent academic institutions such as Berklee College of Music and the New England Conservatory of Music. Mr. Walcott cleverly decided to hire these young music students and mixed them with seasoned professionals who were veterans of the Big Band era. This mix of talent was special, and the format enabled Mr. Walcott to continue to serve the jazz loving audiences of New England. After Wally’s death in 1998 at age 101, his three children took over the bar, and today Wally’s Cafe is still owned and managed by his family, though presently closed due to COVID-19 restrictions.

Lewis and Harriet Hayden House // 1833

Lewis Hayden was born into slavery in Lexington, Kentucky, in 1811, as one of a family of 25. Hayden was first owned by a Presbyterian minister, Rev. Adam Rankin. He sold off Lewis’ brothers and sisters in preparation for moving to Pennsylvania, and he traded 10-year-old Hayden for two carriage horses to a man who traveled the state selling clocks. In the mid-1830s, Hayden married Esther Harvey, also a slave. She and their son were sold to U.S. Senator Henry Clay, who sold them both to the Deep South, and Hayden never saw them again. By 1842, Hayden married a second time, to Harriet Bell, who was also enslaved, and he cared for her son Joseph as his stepson. After this marriage, Hayden began making plans to escape to the North, as he feared his second family might be split up like the first. In 1844, he and his family escaped with assistance of abolitionists all the way to Canada. From Canada, the Haydens moved in 1845 to Detroit in the free state of Michigan, and the next year, they moved to Boston, at the center of anti-slavery activity with the city’s strong abolitionist base. In Boston, Hayden became a lecturer and ran a clothing shop, acquiring enough money to live in this large home in Beacon Hill. The Haydens routinely cared for fugitive slaves at their home, which served as a boarding house. Guests included Ellen and William Craft, who escaped from slavery in 1848. Hayden prevented slave catchers from taking the Crafts by threatening to blow up his home with gunpowder if they tried to reclaim the pair. Hayden died in 1889, outliving the abolishment of slavery. Harriet died in 1894 and left $5,000, the entirety of their estate, to the Harvard University for scholarships for African American medical students. It was believed to have been the first, and perhaps only, endowment to a university by a former slave. Their former home remains a stop on Boston’s Black Heritage Trail.

Glapion-Middleton House // 1787

George Middleton and Louis Glapion built this two-family residence in Boston’s Beacon Hill neighborhood in 1787, which is now the oldest extant home on Beacon Hill. This wood structure is a typical example of late 18th century Boston homes built by African Americans. Louis Glapion worked as a hairdresser and may have been from the French West Indies. Glapion lived and ran his business out of 5 Pinckney Street until his death in 1813. His wife Lucy continued to live there until 1832. George Middleton was a “horse breaker” (horse trainer) by trade and was adored in the diverse community of Beacon Hill. Middleton was one of 5,000 African Americans to serve in the military on the Patriot side of the Revolutionary War, leading an all-Black militia called the Bucks of America. The group is believed to have guarded the property of Boston merchants during the Revolution. After the war, he became the third Grand Master of the African Lodge, later known as the Prince Hall Masons. In 1796, Middleton founded the African Benevolent Society, which helped orphans and widows through job placement and financial relief. He died in 1815, outliving his wife and apparently left no children when he died in 1815.

Oak Bluffs Town Hall & Fire Station // 1882

Located at the heart of Oak Bluffs, this modest, wood-frame building has held some of the most important civic and cultural uses on the island. Built in 1882, the growing town of Cottage City (later renamed Oak Bluffs), which separated from Edgartown, needed a new town hall and fire station with the rapid development caused by summer visitors and increased year-round residents. After WWII, the property was renovated and expanded to allow space for a small police department in the building as well. In 1966, a new town hall was built across from the ferry pier at the waterfront, and the town soon after sold the former, outdated building, and two years later, it was purchased by The Cottagers, Inc. The Cottagers, Inc., is a philanthropic organization founded in 1955 by a group of African-American women who owned cottages or homes on Martha’s Vineyard. The social group provided a safe space for the growing Black community who lived on and visited Martha’s Vineyard. The building remains as an iconic landmark not only for its historical use and architecture, but as a symbol of the diversity and the black community in the small island town.

Aunt Georgia’s House // c.1880

Located on the iconic Circuit Street in Oak Bluffs, this Eclectic Victorian cottage has a storied past related to Black history on the island. Even though Oak Bluffs was a relatively safe place for African Americans to be, there were still limits on their rights. In some parts of Oak Bluffs there were laws that said that certain property could only be owned by whites. The island became a vacation spot for thousands every summer in the 19th century and seeing a lack of options for Black travelers, Mrs. Georgia O’Brien and Ms. Louisa Izett began to operate an inn for people of color. The inn was one of two such residences in Oak Bluffs and has since been listed on the African American Heritage Trail of Martha’s Vineyard. The home has since been named the Tivoli Inn and retains much of the original gingerbread trim. In recent years, Martha’s Vineyard was given the nickname, “The Black Hamptons,” due to its popularity as a place for wealthy African-Americans to vacation, it remains a very diverse island in summer months.