Martha's Vineyard!

Recently, I was able to visit Martha's Vineyard for the first time, and I have to say that it was not what I was expecting (in a good way).

First, I'll dive into a bit of history about the island. Then, I'll share the details of what I did while on the vineyard. Finally, I'll share some general things to keep in mind if you're planning a visit there.

Martha's Vineyard History

The original inhabitants of the island are the Wampanoag people. They are still on the island specifically in the portion called Aquinnah. If you choose to visit the island, please be respectful of their land and follow all rules and regulations. In addition, try to support the businesses in Aquinnah since they are all owned by tribal members.

Contrary to popular belief, many of the Black people who own homes on the vineyard are not upper class. Many of the families purchased their homes generations ago for prices that were affordable for working class families at the time. These homes have been passed down and are now worth significantly more, but we should not assume that all homeowners on the vineyard are wealthy.

There are multiple subsets of people on the island at any given time. There are year-round residents, summer residents and tourists who visit for a week or two at a time (especially during August which is particularly popular). The experience of being on the island is different for each of these distinct groups of people.

There are tours that you can take to learn more about the history. Specifically for Black history, the African American Heritage Trail conducts tours. Proceeds from the tours support operations, scholarships and other efforts.

My Experience

Sunday, August 9

We arrived on the vineyard on Sunday, August 9. We rented a room on Airbnb since there were only two of us and that seemed to be the best (possibly only) option by the time we were booking. After checking in, we headed down to Menemsha beach, picked up some food from Larsen's Fish Market and watched the sunset.

Monday, August 10

On Monday, we started our day with brunch at Artcliff Diner. We then attended a reception and tour near Inkwell Beach hosted by my sister's undergrad university. Finally, we spent some time exploring Edgartown before calling it a night.

Tuesday, August 11

To start our day, we stopped at Mocha Mott's for some coffee and at MV Salads for some lunch. One note about Mocha Mott's for any matcha lovers: I believe their matcha is pre-sweetened so be mindful of anything you choose to add to it. MV Salads was quite expensive for a salad, but the salads were very tasty and quite substantial. We were able to have some for lunch then eat the remainder later during a break at the film festival.

We made a quick stop at East Chop Lighthouse, but we spent most of the day at the Martha's Vineyard African American Film Festival. Specifically, we saw:

• The Lorraine
• The Art of Possible (Vineyard Lounge)
• Montmartre

The Lorraine is a documentary about the Lorraine hotel in Memphis, Tennessee that has since been turned into the National Civil Rights Museum. I was already aware of the hotel, but I learned a lot more about the journey the owners took to get the hotel open and keep it open despite the impacts of economic conditions, integration, etc.

The Art of Possible was part of the Vineyard Lounge programming which was open to the public. I wanted to support this session

because Marian Croak is an inspiration to me personally as a Black woman in the tech industry. She is one of few Black people in the Inventor's Hall of Fame and holds over 200 patents. I would recommend checking out the short documentary about her journey on Youtube.

Montmartre was an interesting romantic film. I won't go into too much detail about it since I don't want to spoil it for anyone wanting to watch. However, I will say that it is a bit different than your typical romance. The filmmakers mentioned having additional stories to explore about the couple, so maybe we will get some sequels?

After the film festival, we stopped at Fat Ronnie's for a burger and attempted to get some donuts from Backdoor Donuts, but they were unfortunately sold out of the ones we wanted. The burgers at Fat Ronnie's are quite large (8 oz), so my sister and I were able to share one especially since we weren't super hungry after eating the large salads earlier in the day.

Wednesday, August 12

We again spent the day at the film festival. We first attended a block of short films that included:

• Hatchlings
• Basement People
• Ella
• The Philadelphia Sensei: Lovett Hines
• Food for the Soul

I won't go into too much detail on all of these, but I enjoyed all of them. The first 3 were nominated in the "Best Short Film" category. Many of these also seemed to me that there was a lot more that could be explored. Basement People in particular already has a feature-length script written, but the screenwriter is currently incarcerated, so I think that there are some hoops that may need to be jumped through to get this done. I enjoyed that many of these focused on mental health in some capacity and were centered around cities that are key focal points in the Black community (Detroit, Philadelphia).

After this, we took a break from the film festival to have lunch at Biscuits. The wait can be quite long, but thankfully it wasn't too bad around 1:30pm when we arrived. You can also place a to go order if you don't want to wait for a table. I kept it simple and had some biscuits and gravy.

Back at the film festival, we watched a documentary about Stuart Scott who was a pioneer in sports reporting. He was one of the people who started at ESPN in it's early days and was also a trailblazer for Black sports reporters in particular. I especially enjoyed the "Colors of Conversation" following the screening where we were able to hear from his ex-wife who shared the experience of her and their two daughters throughout his life and the filmmaking process.

We ended the day with dinner at Atria. I had duck breast which was very tasty. My sister's scallops were good as well.

Thursday, August 13

We started the day at South Beach. It was nice to lay out and get some sun, but unfortunately the water was a bit cold to actually swim in. There are plenty of sea birds roaming around, but be careful of them. Posted signage indicated that they often have rabies 🫤.

We then attended a "Voices of the Vineyard" event. Personally, I think it's important to travel responsibly and be aware of the history of places you choose to visit. This event included a panel of 3 women who are key members of the Martha's Vineyard community: the founder of the African American heritage trail, a member of the Cottagers (a Black women homeowners group), and a leader in the Wampanoag tribe. This event (along with the previously mentioned tour) is where I learned much of the history that I shared in the section above.

After the event, we had happy hour at the Pelican Club then headed to Lambert's Cove Inn for dinner. We got a table with no issue at the Pelican Club, but it was fairly popular around this time, so a larger party may have more difficulty. Dinner at Lambert's Cove Inn was probably one of my favorite parts of this trip...not so much because of the food but because of the garden! If you choose to go here, definitely request a garden table pre-dusk for the best light and amazing pictures.

After dinner, we tried Backdoor Donuts again, and this time it was a success! We got an apple fritter and a maple bacon donut. The apple fritter is the most popular choice, and for good reason. It's quite large so you can definitely share.

Friday, August 14

By this time, we were pretty tired, but we hadn't yet made our way to Aquinnah. We first stopped at the Orange Peel Bakery. This bakery is owned by the same Wampanoag woman who was on the Voices of the Vineyard panel. She built a wood-fired oven herself and opened this pay-what-you-can, honor system bakery that has been operating for 20 years. We picked up multiple items and also contributed extra to support the bakery and cover anyone who can't afford the cost of their items.

We then went to the Aquinnah cliffs. There is a beautiful overlook where you can see the cliffs as well as Gay Head lighthouse. You can also visit the lighthouse itself, and climb inside it for a $6 fee. Fun fact, the lighthouse actually had to be moved because the original location was at risk to erosion on the cliffs. All of the business in this area are owned by the Wampanoag people, so this is a great place to do some souvenir shopping and support the native population. There were food vendors as well.

After exploring, we went to Nancy's for lunch followed by a drink at Donovan's Reef before relaxing for the remainder of the day since our ferry off the island was quite early the next morning.

Tips and Tricks

Book early! Book everything early! If you want to go in 2027, start getting your ducks in a row now and plan to book by the end of 2026 if possible. Hotels, Airbnbs etc are quite scarce and pricey during August especially. Ferry reservations if you want to bring a car can also fill up quickly (it's easy without a car). Film Festival tickets can sell out as well if you're looking for multi-day passes. These were sold out before they even posted the itinerary.

Plan to spend $$$. Restaurants are expensive, drinks are expensive, lodging is expensive, gas on island is expensive, Lyft/Uber is expensive. Just make sure you're prepared. Don't show up looking for a budget vacation because you won't find it here...at least not during peak season. I've seen some people online say that they visit off-peak when housing is significantly cheaper. You can also keep costs down by cooking at home if you have the facilities to do so.

Download offline maps. Phone service is not great with any of the carriers. If you're going to be driving around, you will want to have offline maps so that you can still navigate without service. Also, make sure the place you're staying has wifi.

If you plan to explore different part of the island, you might want a car. My sister lives in Connecticut, so we were able to drive over, and having a car made things significantly easier. If you only plan to stay within one area and are mostly looking to relax, a car won't be as necessary. There are also buses available which are apparently free. I'm not sure where exactly they go or how efficient they are, but I would definitely look this up ahead of time if you won't be bringing a car. If you want to attend the film festival, the location is not near the main places where people stay, so you'll definitely need transportation for that at least. I've heard that there are long waits for ride-shares. Taxis may be better.