An expert-led 90-minute walking tour tracing the remarkable, largely untold story of African American life on Martha's Vineyard — from the Inkwell Beach enclave to the grand Victorian homes of the Highlands. Profound, moving, and utterly exclusive to this island.
What to expect
Your guide leads a small group along Oak Bluffs' storied streets, pausing at landmarks tied to figures including Dorothy West and Adam Clayton Powell Jr. The Inkwell — one of New England's most historically significant Black beach communities — is a centrepiece, its context both joyful and deeply resonant. The pace is leisurely and conversational; questions are warmly encouraged. You'll leave with a richer understanding of the island than nearly any other visitor.
Good to know
Book directly through the Heritage Trail website; group sizes are intentionally small. The route is relatively flat and walkable. Allow 90 minutes plus leisurely time at each stop. Check departure times against your all-aboard schedule and confirm the meeting point when booking.
Sail there
Luxury cruises that call at Oak Bluffs — book through us, the fare is identical and your concierge stays on your side.