Shearer Cottage, Dorothy West, the Inkwell and 30 marked sites across the island: how to walk or tour the African American Heritage Trail of Martha's Vineyard.
Fact-checked August 20, 2026 against the Heritage Trail organization's own materials. Site counts and tour offerings change as new locations are dedicated, so confirm details when you book.
Most visitors know Martha's Vineyard as a beach island. Fewer know it holds one of the most significant concentrations of African American history anywhere on the New England coast: a story of freedom seekers, whaling crews, Methodist camp meetings, Harlem Renaissance writers and a summer community that turned Oak Bluffs into a haven when much of America offered Black travelers nothing of the kind. The African American Heritage Trail of Martha's Vineyard marks that story in bronze, 30 sites and growing, and it is one of the best free things you can do on the island.
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The trail is the work of a nonprofit begun in 1989 by an island teacher and an NAACP leader, who dedicated the first marker in 1998, who realized the island's Black history was being told nowhere. Each site carries a marker and a story researched with descendants and primary records. There is no gate and no ticket: the markers stand in public view across all six towns, with the heaviest concentration in Oak Bluffs. You can walk pieces of it on your own for free, or book a narrated tour with the organization itself, which is where the stories come alive.
Sphere of Influence, a Lois Mailou Jones exhibition poster outside an Oak Bluffs gallery, running July 9 to September 13, 2026.
Shearer Cottage is the natural starting point. Charles Shearer, born into slavery in Virginia, and his wife Henrietta, born free in Lynchburg, opened their Oak Bluffs guesthouse in 1912: the island's first Black-owned inn, later listed in the Green Book, and the seed of the summer community that would earn the Highlands the nickname "the Black Beverly Hills." Guests over the decades included Paul Robeson, Ethel Waters and Adam Clayton Powell Jr.
Dorothy West, the youngest and last surviving writer of the Harlem Renaissance, summered and then lived in Oak Bluffs until her death in 1998. Her novel The Wedding, set in the island's Black summer community, was edited by her Vineyard neighbor Jacqueline Kennedy Onassis. Her home is a trail stop, and her presence still hangs pleasantly over the Highlands.
The Inkwell, the stretch of town beach near the Oak Bluffs ferry landing, is usually said to have got its name as a slur from white summer residents, though other versions of the story circulate. The community kept the name and made it an emblem: today it is one of the most famous Black beaches in the country, five minutes on foot from the ferry, free like every Oak Bluffs beach.
The trail's reach extends well past Oak Bluffs, and it keeps growing. One of the most powerful recent additions tells the story of Esther, an enslaved woman who escaped through Edgartown, a story now recognized in the National Park Service's Underground Railroad Network to Freedom. Other markers stand in Edgartown, Vineyard Haven, up-island farms and burial grounds, tracing lives from whaling-era crews to twentieth-century civil-rights figures.
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Self-guided is free. The markers are public, and Oak Bluffs alone makes a satisfying walking loop: the Inkwell, Shearer Cottage, Dorothy West's home and the surrounding Highlands sit within a comfortable walk, and our Inkwell Beach walking tour covers the neighborhood in detail.
Guided tours are the full experience. The organization runs narrated tours through the summer season, with Oak Bluffs, Edgartown and all-island options, plus walking tours of Vineyard Haven or Edgartown at $50 per person on request. Booking goes directly through the trail: call 508-693-4361, book at mvafricanamericanheritagetrail.org, or email the trail office. Proceeds fund the research and new markers.
Pair the trail with the season's cultural anchor if your dates allow: the Martha's Vineyard African American Film Festival, the largest of its kind east of the Mississippi, runs in Oak Bluffs each August and just completed its 24th edition.
Several trail sites are private homes and an active church community. The markers are on the sidewalk and so is the view; the history is public, the houses are lived in.
For the wider Oak Bluffs picture (the Campground, the Flying Horses, the harbor), see our Oak Bluffs town guide. And if this side of the island's history interests you, the Wampanoag story at the island's other end belongs on the same trip: our guide to visiting Aquinnah respectfully covers it.
Island tip of the dayTimingNo. 80 of 86New tip at midnight, island time
Lambert's Cove Beach is resident-sticker in summer (locals sometimes wave walkers in after 5 PM, but don't count on it); from mid-September it opens to everyone.
Joshua Slocum, first to sail alone around the world, spent his last years farming in West Tisbury and vanished from Vineyard Haven harbor in November 1909. The voyage, the farm called Fag End, the last departure, and what a visitor can actually see: the harbor, a marker stone by a country road, the museum's Slocum papers, and the book itself.
Who summered where on Martha's Vineyard, and what a visitor can actually see: Eisenstaedt's Menemsha, Benton's Chilmark, Cronkite's Edgartown harbor, Styron and Buchwald in Vineyard Haven, McCullough and Katharine Graham in West Tisbury, Belushi's grave at Abel's Hill, and the Onassis farm in Aquinnah that opened to the public in 2025. Public places named, private homes left alone.
The red bus that gets the loudest cheer in the Edgartown Fourth of July parade belongs to Camp Jabberwocky, a tuition-free summer camp for people with disabilities that has run on the Vineyard since 1953. An islander's account of where it came from and what it is. For anything official, the camp's own site is the source.
The Feast of the Holy Ghost in Oak Bluffs, held every third full weekend of July since 1928: the Queen Isabel legend behind the free soup, the Sunday parade from the ferry up Circuit Avenue, the crown blessed at Our Lady Star of the Sea, the sopas at the Portuguese-American Club, the club the rest of the year, and how a visitor should behave at the island's Portuguese feast.
The words you will hear on Martha's Vineyard and what they mean: up-island and down-island, on-island and off, going to America, the boats, wash-ashore versus native, Five Corners, the Triangle, the Blinker, Chappy, OB, the Campground, the Derby, the Fair, island cars and the Vineyard shuffle, with pronunciations.
East Chop Lighthouse in Oak Bluffs: the 1878 cast-iron tower on Telegraph Hill, the Sunday sunset openings run by the Martha's Vineyard Museum, the semaphore and Chocolate Lighthouse history, and the bus stop and parking below the hill.
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