How To: Martha's Vineyard

I had never been to Martha’s Vineyard before. I imagined there would be preppy guys dressed in Polo Ralph Lauren shirts, girls in tennis skirts, and wealthy people just hopping off of their yachts and ready to enjoy their million-dollar Martha’s Vineyard beach-front houses. My experience, however, was very different. My boyfriend’s family and I decided to go down to the Vineyard early October, since the peak season was ending and all that would be left would be locals and a few other late vacationers. We drove down to Woods Hole, stopped at Pie in the Sky Bakery & Café where I had a delicious oat apple streusel muffin and soy chai latte (ok, that definitely sounded stuck up, but in my defense, soy chais are delicious). We then waited in the car in line to board the ferry. I was a bit nervous about getting on a boat while also being in the car, I felt like a sitting duck. So, once aboard, we all climbed the rusty, tiny ladder up to the front of the ship. I stood near the railing, watching as we left the Cape Cod shores and sailed the short distance between the Massachusetts coast and the Vineyard.

During this forty-minute ride, I constantly fought with my hair, which had decided to attack my face for the duration of the journey. Whenever my hair allowed, I watched a family next to me. I watched as a four-year-old girl dug her tiny hands into a Cape Cod potato chip bag and I couldn’t help but smirk. Her younger brother would come by every couple of minutes and aggressively shove his hand in the bag, managing to grab a few chips, most of which would immediately fall out of his mandarin-sized hands. Adorable, and yet infuriating (also, who lets chips go to waste?!).

As we got closer to the Vineyard, I started to see pintoresque lighthouses and million-dollar mansions poking out of lush woods. I immediately started pointing to the ones I would one day buy and only come once a year to. We passed Vineyard Haven and finally docked into Oaks Bluff—the typical Martha’s Vineyard town—full of quaint souvenir shops, and Vineyard Vines and Black Dog stores. Once on the island, we took a wrong turn and instead of driving ten minutes southeast to Edgartown (where we were staying), and drove toward Aquinnah, where we stopped to take iconic lighthouse pictures and look at the waves hitting the cliffs. If you tried hard enough, you could almost believe you were in Scotland, in the Highlands, overlooking one of their impressive cliffs. Later, we drove through the remaining towns, though they were just mostly t long twining roads engulfed in a sea of trees. Again, I felt that if I was dramatic enough, I could be the protagonist of one of those movies where the camera zooms in on your pensive face as you look out the window, the image of the trees reflecting off the glass.

When we finally arrived at Edgartown, the town was desolate. It was kind of creepy, but at the same time exciting that we got to enjoy it without having hundreds of people crammed into the same narrow sidewalk. We had a late lunch at Newes From America Pub, a place I considered to be a tourist trap, but I kept my mouth shut because I was with six other hungry people. After a mediocre lunch, we walked through the streets (somewhat surprised and somewhat expecting to see a Lululemon Athletica store) and made our way back to the hotel. While the older members of the party dozed off for their afternoon naps, my boyfriend, his brothers, and I went over to Bad Martha’s Farmer Brewery where they drank and I played cornhole (for the first time ever!). There were a few friendly locals enjoying their happy hour under a canopy of lights in the chilly October weather. We were one of the last groups to leave; I remember thinking how great this place would be in the middle of the summer, when the nights are long and the beer doesn’t leave you frozen.

Fast forward to Sunday morning, also known as Apocalypse Sunday or Noah’s Second Calling. I woke up to what seemed to be Hurricane Matthew—the wind was blowing hard and the rain was falling like I had only seen in tropical storms or hurricanes as a child. Nothing like the gentle drizzle of Somerville, that I have become so accustomed to. So, at the mercy of the rain and the wind, we ended up at Espresso Love in Edgartown, where I munched on a blueberry scone and drank a latte in a sunroom, void of sun. Instead, I was surrounded by a surprisingly peaceful thunderstorm and the sweetest (and smartest) Pit bull I’ve met; Nico, who gave me a double high-five and enjoyed a bite of my scone!

After breakfast, we drove to Chappaquiddick Island and in a foolish attempt to see the infamous bridge where Ted Kennedy had his incident, our car got stuck in the sand. Naturally, I had a panic attack. I got out of the car and treaded the sand, looking for a spot to calm down. The rain was falling hard and my shoes were full of sand, but anywhere was better than inside that car. Luckily, after a few minutes, the men in the group managed to set the car free and we were on our way back to the mainland. Shortly afterward, we decided that the weather wasn’t going to let us enjoy the rest of the day so we headed back.

We were on standby for an hour, waiting for the seemingly-never-arriving ferry back to Woods Hole. Again, I was nervous about the trip back, fearing that the weather might impact the otherwise smooth ride. Once we got on the ferry, it was rough; the sea seemed angry that we were leaving the Vineyard, but reality was calling and we had to get back to Boston. After a few minutes in the car, I abandoned it and went up to the deck, where, despite the strong winds and torrential rains, others passengers stood and chatted. I got soaked, but I didn’t care. I had always enjoyed being out in the rain and soon as I saw that we were near the port, I went back in the car to change my drenched shoes and damp socks.

My trip was short and limited, but in my time there I got a glimpse of what life in the Vineyard is like; peaceful and laid-back, a lot like it is back home in Puerto Rico. So, although I’m not a white girl enjoying Martha’s Vineyard, I’m definitely an island girl enjoying one of New England’s most beautiful islands.

Photo By: Antonio Figueroa