Martha's Vineyard with Kids: The Complete Family Guide (2026)
Martha's Vineyard with kids: best beaches, Flying Horses Carousel, free VTA buses, kid-friendly restaurants, rainy day plans, and family budget tips.

Walking tour of Inkwell Beach and Oak Bluffs, Martha's Vineyard. This culturally significant beach and historic Shearer Cottage on a guided walk.
Inkwell Beach on Seaview Avenue in Oak Bluffs is far more than a small harbor beach — it is one of the most culturally significant beaches in America, the center of a Black summer community dating to the 1890s and a symbol of reclaimed pride that has shaped Martha's Vineyard's identity for over a century.
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The African American summer community in Oak Bluffs was founded in the 1890s when Black visitors began purchasing property. Shearer Cottage (1912), founded by Charles and Henrietta Shearer, became the first African American-owned guest house on Martha's Vineyard and is still operated by Shearer family descendants. Oak Bluffs was the only town that welcomed Black tourists during the segregation era.
Notable figures connected to the community include Dorothy West (last surviving Harlem Renaissance member, lived in Oak Bluffs until 1998), Martin Luther King Jr. (stayed at Villa Rosa, reportedly wrote speeches on Oak Bluffs porches), Adam Clayton Powell Jr., President Barack Obama (vacationed 2009–2011), and Maya Angelou.
Founded in 1946 by a group of Black women, the Polar Bears meet every day at 7:30 AM at Inkwell Beach between July 4th and Labor Day for swimming, water aerobics, prayer circles, and community bonding. The name refers to the early morning chill of the water. Still very active after nearly 80 years — intergenerational, inclusive, and deeply connected to HBCU alumni.
"Inkwell" was originally a derogatory term used by white beachgoers. The Black community reclaimed the name with pride as a symbol of cultural identity — now described as "the most famous of beaches to transform this odious nickname into an emblem of pride."
Located along Seaview Avenue, positioned between two jetties bordering Nantucket Sound just south of the Steamship Authority pier. The beach is small, sheltered, and calm — warm, shallow water good for children. Less than a 5-minute walk from the Oak Bluffs ferry terminal. Free public beach, no entrance fee. The African American Heritage Trail includes multiple stops nearby: Dorothy West's home, Shearer Cottage, Bradley Memorial Church, and more.
For the complete Oak Bluffs experience, see our Oak Bluffs Town Guide (2026). Getting here is easy with the free VTA bus.
💡 Island Tip of the Day — Timing
Edgartown Lighthouse is climbable 10 AM–4 PM daily in summer. Shortest wait right at 10 AM and just before 4 PM. $5 admission. Staff may close the door a few minutes early.
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Your insider guide to Martha's Vineyard — beaches, dining, events, and island living. We share local knowledge to help you plan the perfect Vineyard getaway.
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