African American Heritage Trail
One of Trina's highlighted ways to explore the island's Black history.
Explore
Find your kind of Vineyard day
Browse Trina's original ideas by mood instead of following a fixed itinerary. Pick what sounds good, skip what doesn't, and make the trip your own.
Black Culture & History
Start with the experiences that make this trip special
Inkwell Beach
A culturally significant Oak Bluffs gathering place and a recurring stop in Trina's notes.
Cousin Rose Gallery
Included in the Black-owned businesses and culture day.
Mariposa Museum & World Culture Center
Another culture-focused stop from the planning document.
Black Joy Kitchen
Sunday brunch, BBQ and DJs · 10 a.m.–4 p.m.
Noman's
Friday–Sunday · 6–9 p.m. · Black DJ, Black crowd, dancing under the stars.
Special Events
Things to watch for during the trip
Legacy Week · worship serviceRich Aunties & Rose BrunchAfrican American Film FestivalComedy FestGrand Illumination NightBlack Fashion WeekendVibe FestBlack Book FestFairsConcertsRoad Races
Event dates and availability for August 2029 will need to be confirmed later.
Beach & Water
Beach days and water time
Inkwell Beach
Beach day, quick dip, beach yoga with Christopher Simms, and the Polar Bears.
The Polar Bears
Inkwell Beach · 7:30 a.m. plunge, water aerobics and stretching · free.
South Beach
A free beach option in Trina's notes.
State Beach
Includes the JAWS bridge stop.
Donavan's Reef Beach Bar
Included with Trina's State Beach day.
Sunset Sail
MV Charter Co. is the optional sail noted in the original itinerary.
Food & Coffee
Places from Trina's list
Coffee
- Mocha Mott's · Circuit Ave.
- Aalia's · Kennebec Ave.
- Tocco Puro Coffee · Circuit Ave.
- Highlands General
Casual & Snacks
- Tony's Market · all-day breakfast & sandwiches
- Back Door Donuts · late-night fresh warm donuts
- Vineyard Caribbean Cuisine · Jamaican to-go
- Midnight Taco
- Giordano's · pizza/snacks
- Fat Ronnies · burgers/sandwiches
- Winston's Kitchen · casual takeout
Breakfast & Brunch
- Biscuits · chicken & waffles or French toast
- Behind the Bookstore
- Black Joy Kitchen · Sunday 10 a.m.–4 p.m.
Dinner & Waterfront
- Sweet Life Cafe · reservations recommended in Trina's notes
- Nancy's or Lookout Tavern · waterfront sunset views
- Farm Neck Club
- Honorary Tavern · Jamaican cuisine
- State Road or L'étoile
- Atria or Alchemy
Shopping & Galleries
Browse, shop, and bring something home
Vineyard Haven
Trina notes that Vineyard Haven has shops with better selections, including Lennox & Harvey.
C'est LaVie
HBCU Martha's Vineyard apparel.
Island Life Studio
Deb Santos custom designs.
Black Dog
Basic Martha's Vineyard souvenirs.
Rhone Botanics & Skincare
A wellness/shopping stop in Trina's notes.
Soul Gems by Maria
Another shop Trina saved for the trip.
Explore & Slow Down
Not every day needs a schedule
Gingerbread Cottages
Walk through Oak Bluffs and end at the harbor for sunset.
Aquinnah Cliffs & Gay Head Lighthouse
A scenic island-exploration day.
Menemsha Hills
Included as an optional hike in Trina's notes.
Bike Ride
Oak Bluffs to Edgartown or Vineyard Haven · follow the paths.
Caleen's Day Spa
A slow-down-and-relax option in Vineyard Haven.
Film & Comedy
Martha's Vineyard Film Center for indie/local screenings or The Strand Theatre for comedy events.