A beach in Martha's Vineyard, Massachusetts

My parents have lived near Cape Cod for eight years, but somehow I never made it to Martha’s Vineyard. Maybe I was distracted by other things to do in the area, or perhaps it was my desire to just chill and catch up on sleep when I would go home, but the Vineyard has eluded me for close to a decade.

Yet I hear about Martha’s Vineyard all the time – about its reputation for being an enclave of the rich and famous. How Jackie O built an estate on a large piece of property after Aristotle Onassis died. How celebrities vacation there every summer. How the President plays golf there. It’s safe to say that my expectations were squarely set on lavish.

In many ways, I couldn’t have been more wrong.

Admittedly, the homes are impressive. But everything else is so… modest. Even agrarian. What? How is it possible for the Vineyard to be so rural and humble?

Thankfully, my amazing mother had booked me, her and my older sister on a three-hour van tour around the island with a deeply knowledgeable tour guide with a killer New England accent. I learned so much more on that tour than I ever would have on my own. It turns out Martha’s Vineyard is far more than just shopping and rich people. Who knew.

Read on to find out more about the real Martha’s Vineyard.

(Note: my source for all of the following information is Ken, our tour guide who had encyclopedic knowledge of the island. I’ve fact-checked and linked to appropriate sources where possible. Further proof of how solid that guy was – I didn’t find a single error in his story.)

A Wee Bit of History

Martha’s Vineyard got its name from Bartholomew Gosnold in 1602, when he named it after the thick wild grapes that grew around the island and his eldest daughter, Martha, who died in infancy. He sailed to Cape Cod (which he is also credited with naming) as part of an expedition to colonize the Northeast. The colony failed after a few months and everyone sailed home. Gosnold returned a few years later as an original settler at Jamestown in Virginia, but succumbed to disease shortly after arriving in 1607.

The Wampanoag tribe were the original inhabitants of Martha’s Vineyard, having lived for thousands of years before European settlers arrived. As the Northeast was being settled the island was purchased by Thomas Mayhew, who also purchased nearby Nantucket and the Elizabeth Islands for the grand total of 40 pounds. Contrary to the narrative of most other European-Native American encounters, Mayhew’s first decree as governor was to treat the natives the same as fellow settlers, and to ensure that any land or other dealings were done at fair market value. This ensured that peace remained between the two cultures.

Mayhew and the Wampanoag chief were so dedicated to peaceful coexistence that they learned each other’s languages. The first translation of the bible into Native American tongue was done on Martha’s Vineyard, and the first two Native American graduates of Harvard in the late 1600s were Wampanoag (one was awarded his degree posthumously in 2011).

What’s amazing is there was never a confrontation between a settler and a native on the island, even during wartime.

Martha’s Vineyard continued its legacy of openness and inclusion as the years went by. Free African-Americans lived on Martha’s Vineyard beginning in the 1780s, with Menemsha serving as a hiding place for escaped slaves on the Underground Railroad until boats going to Boston or Maine would come get them. Many immigrants from Portugal and the Azores also settled on the island.

The Tour

Though it was a three-hour van tour, we made frequent stops for photo ops. Our first stop was in Vineyard Haven at a lighthouse.

Lighthouse in Martha's Vineyard, Massachusetts

I feel so short!

Vineyard Haven was where I caught my first glimpse of the glamorous homes lining the shores.

A home in Martha's Vineyard, Massachusetts

Shortly after departing Vineyard Haven, the island became notably sparse. Farms dotted the landscape, growing or raising everything from corn to wheat to cattle to horses. Roadside stands acting on the honor system displayed honey and vegetables that neighbors could pick up at their leisure.

Ken made sure to emphasize that he and most others on the island don’t lock their doors or take their keys out of their cars. Crime is so low – nonexistent, really – that there’s no need to take those kinds of precautions.

A barn in Martha's Vineyard, Massachusetts

Ken also told us that at one time, farmers were offered money to hold onto their farms and not develop the land further. Many farmers took the money and this helped enable Martha’s Vineyard to stay rural. However, with the soaring housing prices on the island, it is becoming more and more difficult for anyone from Martha’s Vineyard to buy their own homes unless they are very wealthy. The island is taking action by constructing affordable condos and taking other measures to ensure that families who have been here for generations are not priced out of their own hometown.

Wild grass in Martha's Vineyard, Massachusetts

Amber waves of grain. Or whatever kind of grass that is.

Martha’s Vineyard has a goal of eventually being self-sustainable. In fact, teaching farms have popped up and many kids from the local schools go to college for agricultural studies so they can come back and farm the land.

Private road in Martha's Vineyard, Massachusetts

Our next stop was at Menemsha Beach in Chilmark, where we took a break to eat clam chowder and lobster bisque. I opted for the lobster bisque and was not disappointed; I scooped out huge chunks of fresh lobster with every buttery bite.

Next up on our tour was Aquinnah. This is where the Wampanoag reservation remains today, and where Martha’s Vineyard’s famous colorful cliffs are located. Though the cliffs’ brilliant orange and gold have eroded significantly over the years, the cliffs are still impressive and show glimpses of the beautiful colors that once characterized the area.

Next, we took a brief spin through Chilmark, where many famous celebrities have homes. This happens to be where President Obama vacations. Ken told us that if you sit on the patio of the general store, you’ll be guaranteed to see a celebrity.

Fun fact: The origins of American Sign Language began in the town of Chilmark due to a large population of deaf people. In fact, by 1854, one in 25 children in Chilmark was deaf (the national average was one in 5,728). Sign language was even taught to all elementary school children until 2001.

Entrance to Jacqueline Kennedy Onassis’s estate in Chilmark

Jacqueline Kennedy Onassis’s estate is also in Chilmark. This is all you can see from the road. The turkey on the left probably has the inside scoop on what’s inside the gates.

Our last stop on the tour was in Edgartown. Edgartown is where all of the high-end shopping on the island can be found. Unfortunately we didn’t have time to shop (as if I could afford anything anyway), so that will be my first stop on a subsequent trip to Martha’s Vineyard!

After the tour, we walked around the town of Oak Bluffs which was where the ferry had dropped us off. Oak Bluffs is famous for its gingerbread homes, built as part of a religious settlement in the town. There are a total of 317 gingerbread cottages on 19 acres of land.

The homes themselves are modest, but their embellishments are far from it. They’re colorful, full of character, and all unique from one another. I felt like I was in a life-size dollhouse community as we walked around.

Gingerbread cottage in Oak Bluffs, Martha's Vineyard, Massachusetts.

One of the colorful cottages.

Oak Bluffs was one of the first planned communities in US, established in 1890s. As a result, the town has a lot of open space due to the planful nature in which it was developed.

After the Tour

After a full day of touring, we were ready to get a bite to eat. My mom recommended Nancy’s Restaurant in Oak Bluffs which has a great view of the harbor. It did not disappoint. My sister and I shared a salmon sandwich and sushi roll. Both were off the chain.

As we left on the ferry, each with a glass of wine in our hands, we talked about how we felt so enriched from our short day trip. My main takeaway was that Martha’s Vineyard was totally different from what I had expected, and it was a place that I would like to go back and explore over a longer period of time.

I am also glad that we went during shoulder season – just after Labor Day. I’ve heard tales from my family of packed ferries that have to leave passengers behind to wait for the next ferry, and crowded streets and shops on the island during high season. We had zero issues with crowds when we went, and the lack of people created a wonderful atmosphere for our visit.

Bottom line: if you have the chance, I would highly recommend a visit, and also highly recommend Ken’s van tour. This post barely scratched the surface with all of the information he gave us.

Additional Reading and Resources from My Mom, a Local Expert and All-Around Awesome Person

  • The History of Martha’s Vineyard (Martha’s Vineyard Chamber of Commerce)
  • Martha’s Vineyard Transport & Tours – We took the 3-hour guided tour in a 14-person full window van with center aisle for $45 per person. Ken Chisolm was our guide.
  • Island Queen ferry, Falmouth, MA – $20 round trip from Falmouth to Oak Bluffs on Martha‘s Vineyard (seats not reserved by date/time – 1st come 1st serve for any cruise). Ticket window opens at 8am. This ferry is much less expensive than other options on Cape Cod. Parking for the Island Queen is $15 per day.
  • Nancy’s Restaurant – located in Oak Bluffs on a dock overlooking Oak Bluffs Harbor.  Casual takeout, or upstairs full service dining room with inside and outside seating with beautiful views.
  • Getting around: The Martha’s Vineyard bus system is excellent and cheap ($1.25 each way between towns).  At Oak Bluffs, visitors can rent bikes, mopeds, motorcycles and cars.

Like what you read? Pin it!

An Inside Look at the Martha's Vineyard You Never Hear ABout

Booking.com