📅 Self-Guided Black Culture + History Tour of Martha’s Vineyard (2026)
MVacay's picks, plus a 2-day sample itinerary for summer visitors
If you told us you wanted a Martha’s Vineyard trip that centered Black history and living culture, this is what we’d hand you. It’s a self-guided 2026 tour that connects the Island’s history as a Black haven with the people and places carrying that legacy today. Use this guide as a starting point, make it your own, or follow the sample 2-day itinerary at the end! Happy exploring!
🧭 How to Use This Guide
One of the best ways to learn this history is through the African American Heritage Trail of Martha’s Vineyard: a nonprofit cultural history project that documents, researches, and shares the stories of people of African descent on MV through a set of marked sites across the Island. Depending on the time of year they also offer guided tours, or if that doesn’t fit in your schedule you can use the Trail’s site pages year-round to do this meaningfully on your own.
MVacay’s Picks: Start with Heritage Trail stops, then layer in living-legacy stops (shops, galleries, food). That’s how you get a trip that reflects both past AND present!
🏘️ Oak Bluffs
These are all within walking distance of Circuit Avenue.
🏛️ Heritage Trail + history stops
🏛️ Martha’s Vineyard Camp Meeting Association / Gospel Tabernacle: A Heritage Trail stop that documents faith, community life, and the Campground story, including the removal of families of color and the later memorial work that made that history visible again.
🏛️ Union Chapel: A historic Oak Bluffs chapel that hosts major summer cultural programming and has long been tied to Black community gatherings on the Island.
🏛️ Cottagers’s Corner / The Cottagers, Inc.: The home base of The Cottagers, a historic organization of Black professional women known for scholarships, service, and cultural programming on MV.
🏛️ Shearer Cottage: One of the most important Oak Bluffs “safe haven” sites, tied to Black-owned lodging and the long history of Black vacation life in town.
🏛️ Dorothy West Home: The former home of Dorothy West, a Harlem Renaissance writer whose Oak Bluffs circle shaped a lasting Black literary and artistic legacy on MV.
🏛️ Dunmere by the Sea: A Green Book-era lodging site that helps visitors understand what “safe travel” meant in real life and why Oak Bluffs mattered nationally.
🏛️ Powell Cottage: Part of the network of cottages and boarding houses that supported Black summer community and generational return in Oak Bluffs.
🏛️ Dragonfly House (Eastman’s-by-the-Sea): A Heritage Trail site tied to abolitionist documentation (John Ritchie’s Civil War diaries), Green Book-era Black lodging, and the Henry family’s present-day community work.
🖤 Living culture anchors
🖤 Mariposa Museum and World Culture Center: A year-round museum focused on Black and diaspora storytelling through exhibits, talks, and community programming.
🎭 The Strand Theatre: A major Oak Bluffs venue for film, talks, and festival programming, including many Black-led events in peak season.
🛍️ Shops + pop-ups
🛍️ C’est La Vie: A Black-owned Oak Bluffs shop known for HBCU and Greek-life apparel.
🛍️ Island-Life Studio: A Circuit Ave shop with art-forward pieces, prints, and gifts.
🛍️ Jubilee: A Black-owned shop that also hosts author/creator events and community moments.
🛍️ Bee Blunt (pop-up): A seasonal pop-up to watch for, known for “Inkwell” crewnecks and branded pieces.
🛍️ Sanctuaire (pop-up): A seasonal pop-up to watch for, known for natural candles and home goods.
🎨 Galleries / art stops
🎨 Cousen Rose Gallery: A long-running Oak Bluffs gallery on Upper Circuit Ave with seasonal shows (their site notes reopening May 23, 2026).
🎨 Knowhere Art Gallery: A contemporary Oak Bluffs gallery that centers Black artists and regularly hosts community-facing programming.
🍽️ Food + provisioning
🍽️ Black Joy Kitchen: Chef Ting’s African Diaspora restaurant with set experiences like Chef’s Table (reserve ahead).
🍽️ Biscuits: An Oak Bluffs breakfast-and-lunch staple known for Southern comfort food (including biscuits & gravy and shrimp & grits).
🍽️ Eleven Circuit: An Oak Bluffs restaurant + bar with a Jamaican-rooted influence alongside American/Southern menu items, and late hours in season.
🍽️ Vineyard Caribbean Cuisine: A Jamaican Oak Bluffs favorite that’s typically grab-and-go / takeout-forward.
🍽️ Winston’s Kitchen: a takeout-only spot with hearty plates for breakfast, lunch and dinner in Oak Bluffs harbor.
🍽️ Fat Ronnie’s: a burger and fries spot on Circuit Ave for fast casual linch and dinner.
🌊 Traditions + gathering places
🌊 Inkwell Beach: The historic Oak Bluffs beach tied to generations of Black summer life and return traditions.
🌊 Inkwell Beach Yoga: A sunrise yoga tradition held on the beach in peak summer weeks (schedule varies by year).
🌊 Polar Bears: A longtime Inkwell-linked morning swim tradition in peak summer (daily meetups in season, with dates varying year to year).
🗺️ Island-Wide Stops
🏛️ Vineyard Haven
🏛️ Grace Church, Vineyard Haven: A Heritage Trail stop that honors Rev. Absalom Jones, Bishop John Melville Burgess, and liturgical artist Allan Rohan Crite through stained glass windows and a mural inside the church.
🖤 Martha’s Vineyard Museum: A strong “context stop” if you want to connect timelines and understand how Black history and Wampanoag history fit into the Island’s broader story.
🛍️ Lennox & Harvey: A Black-owned Vineyard Haven shop known for elevated home goods and gifts.
🎨 Michael Johnson Art Gallery: A black photography and fine art studio tucked away in Vineyard Haven.
🪶 Aquinnah + Wampanoag Context
🪶 Wampanoag Tribe / Aquinnah: Noepe is Wampanoag homeland, and a culturally respectful trip starts with naming that truth clearly.
🖤 Aquinnah Cultural Center: A tribal-led cultural center at the Vanderhoop Homestead with exhibits, oral histories, and seasonal programming; check hours before you go.
🍽️ Aquila: A Native-owned coffee + retail stop with a location near the Cliffs (and another at the YMCA).
🍽️ Gay Head Store: A Wampanoag-owned general store at the Circle.
🍽️ Orange Peel Bakery: A Native-owned bakery known for wood-fired bread and pizza nights.
📅 Sample Itinerary
Day 1: Oak Bluffs (all in-town)
8:00 AM: Breakfast at Biscuits (Lake Ave).
9:00 AM: Walk the Martha’s Vineyard Camp Meeting Association (Trinity Park) first.
9:45 AM: Walk by Union Chapel.
10:15 AM: Circuit Ave living-legacy loop (all close together): C’est La Vie, Jubilee, Island-Life Studio, Cousen Rose Gallery (Upper Circuit).
11:15 AM: Mariposa Museum
12:15 PM: Lunch: Vineyard Caribbean Cuisine
1:30 PM: Sea View / Inkwell history walk and stretch: Dunmere by the Sea, Dragonfly House, Dorothy West Home
6:30 PM: Dinner: Black Joy Kitchen
Day 2: Vineyard Haven + Aquinnah (around the island)
8:00 AM: Breakfast at Eleven Circuit in Oak Bluffs
9:00 AM: Walk by Polar Bears and Inkwell Beach Yoga
10:00 AM: Venture over to Vineyard Haven and browse Lennox & Harvey and see Grace Church
10:30 AM: Martha’s Vineyard Museum
12:15 PM: Drive to Aquinnah (typically ~45–55 minutes from Vineyard Haven)
1:15 PM: Aquinnah Cultural Center first
2:15 PM: Aquinnah Circle and Lighthouse.
3:30 PM: Grab and go lunch from Aquila or Orange Peel Bakery
5:00 PM: Back home to Oak Bluffs to watch the sunset or get drinks at Noman’s or watch a movie/performance at The Strand.
☀️ Best in season: This guide is easiest to explore late spring through early fall, when many stops are open and the Island is in full swing.
📅 Event-agnostic: This itinerary focuses on self-guided stops (not timed programming). For Heritage Trail tours, Union Chapel programming, Strand events, and annual festivals, check MVacay’s Thursday weekly updates.
If I missed something major or misframed a detail, send me a kind note and I’ll happily update! Thanks! - Lis
