Martha’s Vineyard Travel Guide

This travel guide has been a long time coming! When I first moved to Martha’s Vineyard, I knew I wanted to share a historical narrative of the island (#SeeMVwithMe), everything I wore on the Vineyard, and, at last, a travel guide. Since being here, I have wanted to broaden the perspective on what Martha’s Vineyard is truly like and offer up reminders of all the Black contributions and the ways Black culture has been integral to this beautiful space. As a Black woman, I indeed felt comfortable here. I noticed Black Lives Matter yard signs here and there and asked a local if they really meant it or just didn’t want their businesses torched. He confirmed the Vineyard is liberal. Sad we have to think of these things when traveling, but I wanted to verify I have been and do FEEL safe. So often, people hear Martha’s Vineyard and think rich white people. Nah. We belong and have made indelible marks here too. I want Black folks to know that, broaden their views on where to vacation, and fully indulge in all that is Vineyard life. During my #SeeMVwithMe series, so many said they had no idea all the Vineyard offered and never thought twice about finding out…until my posts. Someone from my SAC community even wrote, “Girl you making it look like Black people need to move all up in through there!!!” And you know what? She’s right. Mission accomplished.

So here you have it, folks! My Vineyard recs all from the vantage point of what I have enjoyed and learned about. Just before we get started, be sure to bring your car or be prepared to rent one once you arrive. Vineyard Haven, Oak Bluffs, and Edgartown specifically are walkable, BUT a car is really helpful in traveling in between towns. Keep in mind the island is divided into 6 towns—Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury (Vineyard Haven), and West Tisbury—each with their own specific culture and charm. There are car rentals all over the island especially in Vineyard Haven (I rented from Budget twice and had a great experience!), Edgartown, and Oak Bluffs. If you bring your own car, you can drive it onto the ferry (get your reservation in advance!) Then sit back and enjoy the ride over from the mainland! I hear you’ll see recurring vacationers and have access to a snack bar on your 45 min trip over from Woods Hole. Also, note that some of the below recs are only open in season (June – August), BUT in my experience, there is still plenty to do in the off season as well. Without further ado:

Where to Stay:

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The Edgar Hotel – This is actually where I lived! Only a 10 minute walk from downtown Edgartown and the water. Also extremely close to several restaurants— Town MV is attached!—and a Stop & Shop in case you need groceries.

Summercamp Hotel – The lobby alone makes it absolutely worth the stay! So incredibly chic and right in town in Oak Bluffs. Circuit Avenue—the main strip in Oak Bluffs—is easily accessible from this location…and so are allll the Gingerbread Houses.

The Kelley House – This hotel is also located in Edgartown in the downtown area. Beautiful ocean views and plenty downtown eatery access.

Mansion House Inn – Located right in Vineyard Haven on the Main Street main strip. You can get off the ferry (at the Vineyard Haven port) and literally walk to this hotel. Also, just a short walk away from rental car services. So quaint and so beautiful!

MANY people also find lodging by renting homes. The Vineyard Gazette and MV Times are your go-to’s for rental listings. Definitely try to secure a home months in advance. I’m talking by January.

Where to Eat:

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The best part, right?! The portion sizes at many restaurants are so large! Mom and I decided it’s likely because towns are so walkable. You can just walk those calories right off!

Sarah Brown’s – Black-owned and full of soul! This Circuit Ave gem has peach cobbler that makes your mouth water.

The Pawnee House – Get the vegan bowl and thank me later! There is also an alcoholic beverage that tastes a bit like smoke. I did not see it on the menu, but ask them about it! Such a cute eatery.

Back Door Donuts – It’s the exclusivity for me! A coffee shop by day, but when that sun goes down, people line up at the literal back door of the restaurant to score the sweetest and most eclectic flavor of donuts I’ve ever had. It’s so fun that it’s an Oak Bluffs night time ritual!

Sweet Life – The outdoor dining experience is so beautiful in and of itself—especially at night. The cuisine is divine and simplistic (smaller portions here) and the ambiance is amazing.

Tony’s Market – Fresh deli meat and sandwiches abound!

Ben & Bill’s Chocolate Emporium – Y’all. I initially asked for a size medium cone and the store attendant’s response was, “Are you sure?” HA! Two huge scoops is considered a size small. Real ice cream (none of that watered down stuff). Delicious flavors. GO!!

Linda Jean’s – Really amazing options for breakfast, lunch, and dinner! There is definitely something on this menu for everyone.

Nancy’s – This waterfront restaurant has amazing seafood cuisine and a stunning view. Complete with upstairs deck seating and beauty all around!

Orange Peel Bakery – Run by a member of the Wampanoag American Indian Tribe, this bakery is located up island in Aquinnah. Delicious treats and runs on an honor system. The store owner may not be there, but you can grab your treat and leave the cash there for her.

Black Dog Tavern – The Vineyard Haven location is a store and a café. Really tasty baked goods!

Dock Street Coffee Shop – I am easily swayed by anyone who brings me a breakfast sandwich in the morning, especially when in New England. I loved walking down to this corner restaurant post and getting an egg sandwich + iced coffee. So. Good.

The Wharf Restaurant and Pub – Y’all. Fish and Chips. Clam Chowder. That is all. I just don’t know what else to say. This restaurant is perfection and my fave on the entire Vineyard. I must have eaten there millions of times. The tartar sauce is so fresh and the pieces of cod are huge. Hands down best chowder I tried here. It’s not the basic chowder recipe. They use a special roux and it’s just so good. GO!!

Edgartown Seafood – I tried my first lobster roll here and I must say I was Impressed! Again, all fresh seafood here on the Vineyard. None of that fake stuff! This is a cute mom + pop shop with a great menu.

Edgartown Pizza – SO. GOOD. I know you’re likely here for the seafood, BUT should you desire to take a break, this is a great option! The Edgartown Veggie is my absolute fave item on the menu!

Mad Martha’s – This ice cream is really delicious as well. Again, large portions and a full range of flavors!

Murdick’s Fudge – Since we’re indulging…fudge, chocolate pretzels, peanut brittle galore if that’s your thing. You can taste the sweet and savory from the doorway!

What to Do:

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Mytoi Japanese Garden – Take the On Time Ferry (because whenever it comes…it’s on time. Ha!) a very short distance to Chappaquiddick and tour this beautiful garden. It’s fully lavished with Japanese plants, florals, and architecture. You’ll feel as if you’ve been transported to a completely different country. A must-see.

Menemsha Sunset – A. Sight. To. See. God’s Glory in its finest. Get there at least an hour before the sun is scheduled to set so you can grab a bite to eat from Menemsha fresh fish markets and get your seat for the show. To see those clashing waves in the back—with the Elizabeth Islands further beyond—while that sun goes down? Nothing like it. It’s such a beautifully clear view and absolutely worth seeing.

Methodist Campground – Candy-coated homes with a religious and historical significance! You can walk around the circular structure of the campground and take them all in.

Grand Illumination – On every 3^rd Wednesday in August, the Campground Tabernacle hosts the lighting of the first lantern and visitors from all around can see gingerbread homes decorated with thousands of Japanese lanterns that light up the night. This event was first used to celebrate the arrival of the Massachusetts governor. Now, it’s an annual celebration that draws many!

Ryan Family Amusements – An old skool arcade and definitely a good time for the young folks!

Jaws Bridge – Yep, the very bridge that was in 1975 “Jaws” movie. It marks the separation between Oak Bluffs and Edgartown. And I hear it’s a rite of passage to jump off it each summer…despite the “no jumping” signs lol! Stay safe, y’all!

Bike Trails – There are beautiful bike trails and bike rental shops All. Over. Definitely go for a ride!

Ocean Park – Perfect for picnicking and people watching! And just a short walk from the beach!

Inkwell Beach – The quintessential spot for Black vacationers. This place has seen the likes of soooo many Black literati and is home to the best of the best bonfires and beach parties. I hear Pinkwell is off the chain! Skee Wee, Sorors!

African American Heritage Trail – Like I said, Black folk BEEN on the Vineyard. Take this historical tour and you’ll gain even more insight.

Allen Sheep Farm – So many weddings are held here and when I drove by and saw the ocean view…I could see why. The sheep are so cute and apparently you can go for a visit!

South Beach – Clashing waves and beautiful views. Another really popular beachfront tourists frequent!

Aquinnah Cliffs – The sunsets from here are breathtaking as well. Definitely beautiful for photo ops! There are also amazing shops here full of beautiful homemade items from the Wampanoag Tribal Nation.

Where to Shop:

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C’est la Vie – Black-owned and has just about every kind of souvenir you need! Books, hats, tees, Greek para, Martha’s Vineyard-specific Greek para, magnets, Everything! Everybody Black, famous, and otherwise comes to shop here. And the register area is adorned with the pictures to prove it! Hands down my favorite shop on the island.

Vineyard Vines – Amazing nautical and colorful clothing, perfect for the Vineyard landscape!

Katydid – Beautifully crafted beachfront clothing for the beach, dinner, and a night on the town.

Black Dog – This is just quintessential Martha’s Vineyard. Gotta get a memento here for sure!

Shirt Tales – I LOVE the shirts here! This is where I got my Vintage Vineyard sweatshirt. Obsessed!

And of course, there are so many local small business on the main strips—Circuit Ave in Oak Bluffs, Main Street in Vineyard Haven, and Dock Street in Edgartown. Support, support, support!

Where to Praise:

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Union Chapel – ICONIC. New preachers every Sunday, Black elite in the pews. Be sure to get there early so you can grab a seat, but I hear the message resounds just as well if you listen from the open windows.

Campground Tabernacle – Just as beautiful in its Sunday messages as it is for its historical significance. The outdoor Tabernacle is beyond stunning and provides a communal sense while receiving the Word.

So there you have it! My MVY recs! This idyllic island is so special and has been so good to me. It truly is a wonderful place and I am just so glad I was able to experience it for an extended period of time. Even as I write this, I am astounded at all I was able to do even during the off season. I will absolutely be back in the summer months to take advantage of the in-season items on this list. I hope y’all enjoy and love the Vineyard as much as I do. Let me know what you try! Love from MVY.

xx,

Photos by Tina Smith