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My 5-Oh! road trip!

In the North East corner of Martha’s Vineyard, an island off Massachusetts, USA, is the town of Oak Bluffs, a magical historical and cultural core of living Black American history.

To get there we, my sister and I took a nine hour road trip from Ontario Canada, over the border into the US, through the Adirondack Mountains, down through New York State until we finally reached the tip of Massachusetts.

We arrived in Oak Bluffs via the ferry, and stepped into the most unexpected place of historically charming gingerbread houses, traditional manners and rich culture set in the middle of a diverse population of people from all walks of life.

The island area, known for being one of the wealthiest black resort communities, is bright and alive with charismatic cottage inns and restaurants, most established in the early 1900s and currently run by family members and generations of their descendants. 

Not at all what I expected from the place known as ‘The Kennedy’s Playground.’ 


Oak Bluffs is the place where elite African American families go to vacation and experience their rich history.   It was in the 1600s that the first slaves arrived on Martha’s Vineyard as apart of European households.  Later, after slavery was abolished, through the 1800s to the 1960s, the Oak Bluffs Harbor ushered in fleeing and freed slaves who bought land from the locals and established themselves through churches and businesses and by building summer homes as the area’s population flourished.  Time made it tradition for families to return to the island annually, Oak Bluffs being the only place on the island that welcomed African Americans until the 1960s.

The Inkwell, pejoratively named though now a statement of pride, is a stretch of the town beach frequented by the black population since the late nineteenth century.  Along the board walk is a collection of benches with carefully crafted and heartfelt engravings that tell the Inkwell’s story.

Past President Obama on vacation in Oak Bluffs.  His daughter got her first summer job at a local restaurant.

I am so happy, honoured and humbled to have had the opportunity to visit this incredible place.  The people were delightfully warm and friendly and willing to welcome you to their little corner haven.  From the time you step off of the ferry, the downtown core is alive with a certain kind of magic that just has to be felt and experienced to be believed.

Download these photos from Martha’s Vineyard to use as backgrounds or screensavers for some armchair travel, or when you just want to enjoy a feeling of happy escape.

Read the blog: Happiness Practices Around the World

Photos from: https://vineyardgazette.com/news/2014/08/07/smithsonian-recognizes-african-american-legacy-oak-bluffs. https://hollywoodlife.com/2016/08/04/sasha-obama-summer-job-uniform-nancys-restaurant-marthas-vineyard-pics/

Historical information from: https://en.wikipedia.org/wiki/Oak_Bluffs,_Massachusetts. https://www.blackpast.org/african-american-history/inkwell-martha-s-vineyard-1890s/


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