A beach in Martha's Vineyard, Massachusetts

My parents have lived near Cape Cod for a decade, but until recently I had never done a tour of 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.

Yet I hear about Martha’s Vineyard all the time – about its reputation for being an enclave of the rich and famous. How Jacqueline Kennedy Onassis built an estate on a large piece of property after Aristotle Onassis died. How celebrities vacation there every summer. How Barack Obama would play golf there.

It’s safe to say that my expectations were squarely set on lavish.

Changing Impressions After a Day Trip to Martha’s Vineyard

When I finally took a day trip to Martha’s Vineyard, I realized that in many ways I couldn’t have been more wrong.

Yes, the homes are impressive. But everything else is so… modest.

Even agrarian.


How is it possible for the Vineyard to be so…pastoral?

My amazing mother had booked me, her and my older sister on a three-hour Martha’s Vineyard tour with a deeply knowledgeable guide who happened to have 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 learn more about the authentic side of Martha’s Vineyard that is rarely talked about.

(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 from our Martha’s Vineyard Tour

The history of Martha’s Vineyard is long, rich, and fascinating.

Martha’s Vineyard got its name from Bartholomew Gosnold in 1602. He wanted to pay tribute to his eldest daughter, Martha, who died in infancy, and also the thickets of wild grapes that grow around the island.

Gosnold 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. He 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 most other European-Native American encounters, Mayhew’s first decree as governor was to treat the Wampanoag people 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 in wartime.

Martha’s Vineyard continued its legacy of openness and inclusion as the years went by. Free African-Americans lived there 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.

Highlights of the Martha’s Vineyard Tour

Our van tour was scheduled for three hours with frequent stops for photo ops. The first stop was in Oak Bluffs at the East Chop Lighthouse.

Lighthouse in Martha's Vineyard, Massachusetts.

I feel so short!

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

A home in Martha's Vineyard, Massachusetts

The setting reinforced my notion of Martha’s Vineyard being a playground for the wealthiest Americans. But shortly after departing the lighthouse, 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 we drove by during our Martha's Vineyard tour.

A barn that we passed during our Martha’s Vineyard tour.

At one time, farmers were offered money to hold onto their farms and not develop the land further. Many farmers took the incentive, which helped enable Martha’s Vineyard stay rural.

However, with 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’re very wealthy. The island is taking action by constructing affordable condos and taking other measures to ensure that families who have resided there 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.

A private road in Martha's Vineyard, Massachusetts.

We made our way along winding roads to 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 enjoyed huge chunks of fresh lobster with every buttery bite.

Next up on the 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.

We took a brief spin through Chilmark next, where many famous celebrities have homes. Ken informed us that if you sit on the patio of the general store, you’re all but guaranteed to see one of Martha’s Vineyard’s famous residents.

An interesting fact about Chilmark is that it is where American Sign Language originated. Chilmark had a large population of deaf people – so many, in fact, that 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.

The 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 lies beyond the gates.

The last stop on the Martha’s Vineyard tour was in Edgartown. Edgartown houses all of the high-end shops and, naturally, more expensive estates.

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 the Vineyard!

After the tour, we walked around the town of Oak Bluffs. Oak Bluffs is where the Martha’s Vineyard ferry docks and is a quaint, historic village.

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.

What the homes are lacking in size they make up for in flair. 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. || How a Martha's Vineyard Tour totally changed my perception of the island – Life As Marissa

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.

Wrapping Up the Day Trip to Martha’s Vineyard

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. My sister and I shared a salmon sandwich and sushi roll. Both were delicious and filling.

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 to Martha’s Vineyard. My main takeaway was that the 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, and packed streets and shops during the summer.

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, spend a day (or longer) on the Vineyard, and be sure to take Ken’s van tour. This post barely scratched the surface of all of the information he gave us.

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

  • 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.
  • The History of Martha’s Vineyard (Martha’s Vineyard Chamber of Commerce)
  • 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.

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