I have wanted to visit Martha’s Vineyard for forever. There was always something so glamorous about it, especially when you learn a lot of celebs vacation there. But actually it’s not glamorous at all, which is what I really liked about it.

Getting There

We debated how to get from mainland to the island and decided to just pay the $250 round trip on the ferry. It made more sense than paying for parking and then renting a car on the island. I don’t know if you’ve noticed, but car rental prices have skyrocketed during the pandemic. If you opt to take your vehicle on the ferry, book way in advance at steamshipauthority.com. We booked more than two months in advance. Spots fill up fast. We also wanted to drive straight to the Aquinnah Cliffs Overlook, so the car was needed.

Accommodations

We stayed at Pequot Hotel in Oak Bluffs. We were upgraded to a larger room upon check-in and it was wonderful. I loved this hotel because it’s within walking distance of all the restaurants and the main shopping street, Circuit Avenue. We chose to stay in Oak Bluffs because of the black history of the town. It’s a place blacks have been vacationing for many, many years and was actually a safe haven for blacks. Inkwell Beach, which was just a five minute walk from the hotel, was and is still a popular hangout for blacks. It’s called Inkwell because many black writers vacationed there. Oak Bluffs has a lot of great hotels and inns, but what sold me on Pequot is they serve freshly baked cookies every day at 4:30pm. You just go into the lobby and grab one……or three. They also have wine nights on Fridays with live music on the porch.

The Architecture

I think what I enjoyed most about Oak Bluffs was the historical feel of the buildings. Many of the houses there were built a long time ago. They’re these huge Victorian homes that make you wonder what went on in there. Do you ever look at a house and wonder what the people are doing inside? Look at this one.

They’re either watching Netflix or having a seance. Who knows?

I was very impressed by the gingerbread cottages. It used to be a camping ground for the Methodist church but then they replaced the tents with these whimsical cottages that pull your attention with their vibrancy. You’re immediately transported to another time once you step onto the property. I felt like a total voyeur walking through the camp. I mean, this isn’t some museum. People actually live here and they’re going about their business of cutting lawns and picking up the mail while you walk around taking pick and oohing and aahing at the beautiful colors. They don’t seem to mind, but I would be irritated if I was trying to sleep in on a Saturday and I can hear strangers outside of my bedroom window asking one another to take a pic of them in front of my house.

The Food

I had been studying for the clinical social work license, which I passed on my first attempt, BTW , right up until we had to leave for MV, so I didn’t really have time to make reservations for any restaurants prior to us heading up there. We got lucky with some of the places we were able to eat because of sheer timing, honestly. MV has good grub.

One of the most surprising places where we ate dinner was The Pawnee House. We had to eat at the bar, which is okay with us. We’re not picky. We just wanted food and alcohol, so the bar was perfect. I had the salmon wellington, which was nothing short of amazing, and Hildon had the chicken pot pie, which was also really good because you know I had to try that man’s food. Ladies, why do we do it? For dessert we shared the strawberry shortcake. Just yummy all around. What stood out to me most was the host was also the bartender, waiter, and I later found out that he owned the restaurant and his wife did the cooking. He was so busy, making sure everyone was okay and making drinks. Guys, he even went outside in the pouring rain to pick fresh mint for my Moscow mule. I had to talk to him after that. He explained that he inherited the restaurant from his dad’s side of the family and they were understaffed due to the pandemic. There was an elderly woman sitting at the back of the bar who looked on at him with such pride. She came over and confirmed that she was his mom. She told us we had to come back for brunch but we couldn’t get reservations. If you’re ever in MV, consider brunch at The Pawnee House. I hear it’s amazing. The menu is everchanging because they use local ingredients only. Everything we ate was so fresh.

Speaking of brunch, one place I can absolutely vouch for is Biscuits. BLACK OWNED! Hello. Do yourself a favor and hit up Biscuits at least once for breakfast/brunch. We went twice, okay? Would have gone a third time had it not been for the rain and having to stand outside in that long line to get in. Yes, it’s THAT good. The biscuits and gravy are the best I’ve ever had. I also had the blackened shrimp over cheesy grits. *chef’s kiss* Hildon had the stuffed French toast that was so good that I had it with fried chicken when we went back the second time. This place is great. I highly recommend.

Every restaurant on MV that serves clam chowder would tell you they have the best but I had it at MV Chowder Company and it is so good. MVCC has great food. The lobster roll was loaded with huge chunks of lobster meat and didn’t have too much dressing, just the way I like it. But the pièce de résistance of the meal was the rum bread pudding. It was orgasmic.

On our third morning on the island, we slept in due to the rain (we love sleeping when it rains) and decided to get breakfast to go at Backdoor Donuts. It’s called Backdoor Donuts because after 7pm they give you the donuts through the backdoor. On Saturday night when we were on our way to dinner, we saw a line of about 13 people standing outside the backdoor of the bakery waiting for their goodies, so we figured it had to be good. Good thing we packed and checked out when we did, because when I for to the bakery the line was almost out the door. I kind of overdid it once I reached the counter.

We then got a call from the ferry company. The rep informed me that the ferry would be leaving from Vineyard Haven instead of Oak Bluffs, so we had to bounce. On the way to the ferry, we drove by Biscuits and were not at all surprised to see a crowd of around 20 people huddled together like penguins, trying to stay warm and dry until that glorious moment their names are called.

The Sites

Apart from the Aquinnah Cliffs, we wanted to explore Chappaquiddick Island. That Friday, otherwise known as the last day we saw the sun that weekend, we took a short ferry ride to the island. We drove toward East Beach, over a little bridge before coming upon a pay booth. We wanted to drive to the Cape Boge Lighthouse and the wildlife refuge, but our lack of planning led to us not being able to get there because our car is not an all wheel drive and you’ll need that if you’re going to drive on the very soft sand on that beach. The elderly couple at the booth said the last thing you want to do is get stuck out there, so we reversed over the little bridge and parked. After we paid $5 each and the man made fun of the fact that Hildon is a Yankees fan based on his fitted cap, I had to take my shoes off to walk on the sand. It was so soft and made walking difficult. We got to the deserted beach and Hildon flew his drone, then we walked back. The lady at the booth said that we should visit the Mytoi Japanese Garden. She said she would phone over there and have them wave the fee since we already paid her, which was very nice. As we were walking back to the car, a large pickup truck with about 8 women in the back was on the way to the lighthouse. I was like that could have been us had we planned better. Maybe next time.

Mytoi Japanese Graden is a lovely getaway from everything else. It was like another world. I love Japanese gardens. So peaceful.

Then we ended up at the Edgartown Lighthouse, which was lovely. I love lighthouses too. I love the way they look but especially what they represent. I see a Lighthouse and I feel safe. Would love to live in one, honestly.

We then walked around Edgartown and had lunch at Behind the Bookstore, a lovely outdoor area just behind Edgartown Books, before perusing books in the store. I bought a couple, naturally.

After the ferry ride back we stopped at the Jaws Bridge on our return to Oak Bluffs. It’s actually the American Legion Memorial Bridge, and it connects Edgartown to Oak Bluffs. It was made famous for the movie Jaws, hence its nickname.

I’m a big kid so you know I had to take a ride on the Flying Horses Carousel. It was just a short walk from the hotel.

The People

Yes, celebs like the Obamas and the Kennedys vacation on the island but the vibe is very laid back. Mostly everyone wore tees, jeans and cargo shorts. I felt a tad overdressed in my wrap top and flats, but was glad I didn’t pack any heels. That would have been embarrassing. If you want to fit in with the locals and not look like a tourist, keep it super casual. But if you’re like me and love a hint of glam, I say go for it. Nothing wrong with standing out.

The people of Oak Bluffs are so friendly. Coming from NYC it was a huge change. Not saying there aren’t friendly New Yorkers. But the people of OB are genuinely warm. And you get this sense of community. Shopkeepers can be heard catching up with regulars to the island, asking them about their kids and how they’ve been coping during the pandemic. I got the sense that everyone knew everyone.

When It Rains

That Saturday on the island was a complete wash out, but we managed to find some indoor activities. We visited the Martha’s Vineyard Museum in Vineyard Haven. It was fun learning about the history of the island.

I only remember a few things from that visit:

Oak Bluffs has been a getaway spot for blacks for over a century. Many middle and upper class blacks vacationed there and eventually bought homes on the island. Shearer Cottage, founded in 1912 by Charles and Henrietta Shearer, was opened to give blacks a safe haven when vacationing, since not many places on the island welcomed them.

There is this cool interactive touch screen in the museum that shows you how the island was formed thousands of years ago. The first humans to set foot on this land, the Native American Wampanoags, are believed to have done so before it was even an island. And if that is true, they bore witness to the melting glaciers forming streams and cutting through the land. The Wampanoags called the land Noepe, which means “land amid the streams.” The cliffs of Aquinnah, where our stay on the island began, tell a story. Many of the Wampanoags still live in the Aquinnah peninsula, where the cliffs continue to erode.

When British explorer Bartholomew Gosnold landed there in 1602 he called it Cape Cod because of the fish in the vicinity. Some people say he named it Martha’s Vineyard after his mother-in-law, others believe he named it after his daughter. The latter is more believable. LOL!

I was shocked to learn that MV was considered part of NY from 1642 to 1692 when it was purchased by colonial businessman Thomas Mayhew in 1641.

And even more shocking is learning that American Sign Language as we know it today is the successor of Martha’s Vineyard Sign Language. One of the earliest known deaf communities in the United States inhabited the island in the late 1600s.

The island was a booming whaling industry until the American Revolution happened and crude oil became more popular than whale oil.

There is so much to learn about the island at the museum. I highly recommend to my fellow history buffs.

Lastly, I did some shopping on that rainy day. I went to Bunch of Grapes Books in Vineyard Haven and bought even more books. Then back in Oak Bluffs I shopped along the famous Circuit Avenue. I hit up black owned C’est La Vie. This store has everything from MV tees and sweatshirts, which a lot of people were wearing because they didn’t expect it to be so cold. Everywhere I turned around that Saturday I saw sweatshirts. People have smartphones and don’t check the weather. Gift shops made a killing that weekend. And, of course, no trip to MV would be complete without a stop at Murdick’s Fudge. I got some rocky road fudge, peanut brittle and a bag of salt water taffy (my favorite).

When shopping on the island, you will notice they have their own brands. Little cafes and clothing boutiques. There are no Starbucks or McDonald’s on the island, although I did spot a Dairy Queen and they have Shoprite supermarkets. Other than that, everything is unique to the island.

Usually after visiting a place I cross it off my bucket list, but MV, particularly Oak Bluffs, felt kind of like home. The people are so welcoming. I definitely intend to visit again. I doubt I would be able to rent or buy on the island since housing there is 96% above the national average, but a long weekend is just enough for me.