The perfect combination of peaceful privacy and simple pleasures - Martha’s Vineyard is home to colorful cottages, lighthouses, white-sand beaches, and restaurants that feel like a friend’s house.
After living on this special New England Island for 12 years, I have a special place in my heart for all things Martha’s Vineyard. So much so I have designed an entire jewelry collection inspired by the island!
Read on for some of my favorite things to do on “The Rock.”
Martha’s Vineyard: history of this seaside paradise
Martha’s Vineyard is an island just south of Cape Cod in Massachusetts that covers about 100 square miles. It was originally inhabited by the Wampanoag Native People, and named Noepe, meaning “Amid the Waters” – a reference to the two distinct and often conflicting tidal currents at work around the Island. Explorer Gosnold later named the island “Martha’s Vineyard,” after his infant daughter, and because the Island was covered by wild grapes.
Martha’s Vineyard was home to one of the earliest deaf communities, where residents developed Martha's Vineyard Sign Language, a predecessor of the modern American Sign Language.
The Vineyard and specifically the town of Oak Bluffs has been a vacation spot for the African American elite and has a rich Black History. For more on that, read this article, and we also recommend this self-guided African American History Tour of Oak Bluffs.
(If you’re interested in reading more about Martha’s Vineyard history, we highly recommend this article from the local chamber of commerce.)
In recent years, Martha’s Vineyard has become a popular vacation spot and second home to well-known personalities including Oprah Winfrey, Larry David, Walter Cronkite, Ted Dansen, Amy Schumer, and Former President Barack Obama.
However, if you ask me, Martha’s Vineyard is less about who you see - and so much more about slowing down, enjoying the moment, and embracing the picturesque views.
How to get to Martha’s vineyard: ferries & flights
You’ve got options! Martha’s Vineyard is an island, so there’s no secret tunnel or road that’ll get you there (as cool as that would be!). But it’s accessible by ferries and planes. Some ferries will take your car as well if that’s important to you.
Generally, visitors from outside of the Northeast will fly to one of the following states: Rhode Island, Massachusetts, New York, or Connecticut. From there, you can drive, bus, or take a train to the ferry.
Check out Go Martha’s Vineyard for in-depth information on transportation options.
Martha’s Vineyard restaurants & foodie spots
Whether you’re craving lobster rolls, biscuits, or chowder - Martha’s Vineyard will have something for you and all your vacay cravings. Here are three of my favorites. PS, you won’t see a Starbucks or Mcdonald’s here - it’s a part of the small-town charm!
This is my absolute favorite restaurant on the island. It’s a bit of a hidden gem in Edgartown and you’ll need to duck into a side street to find it but you won’t be disappointed! Award-winning chef Kevin Crowell will prepare your fresh seafood, accented by locally grown ingredients and delectable desserts. Their expanded outdoor dining section is the perfect finale for your epic island day.
Island Native Juli Vanderhoop wanted to bake so she built a traditional stone oven in her Aquinnah driveway and the rest is history. Biscuits, croissants, muffins - oh my! Just writing this is making me crave a trip up island to this special bakery. In addition to a drool-worthy bakery selection, Orange Peel bakery also serves oven-roasted pizza made with their own artisan dough.
This locally-owned, family-friendly outdoor dining spot offers good food, lawn games, cold refreshments, live music house rum, a great place to enjoy the seasons on Martha's Vineyard. Don’t miss this one-of-a-kind spot!-- dogs welcome too!
Here’s your spot if you’re yearning for a special night out on the island. The Sweet Life has a patio dining situation under a tent that transports you into another world. Complete with mocktails, cocktails, and delectable award-winning menu selections, this place has it all. Plus the chef/owners are really sweet and live in my neighborhood.
My go-to spot for lunch in Edgartown. Always yummy.
Our favorite hotels & home rentals on Martha’s Vineyard
The Nobnocket Boutique Inn is an elegant b&b that's set in a renovated turn-of-the-century home. It's found on a leafy lane outside Vineyard Haven’s center, minutes from the ferry port – but aesthetically, it's a million miles away. Expect chic bedrooms and beautifully curated spaces to relax, indoors and out, and hosts that really know the island.
A haven of the Island, the Winnetu Oceanside Resort is known for its close proximity to the beach and stunning hotel grounds. It’s also a great spot to stay with children, as they have shuttles and kids programs.
Be sure to note that it’s a seasonal hotel, so it’s only open from May to October.
3. Beach House Rentals
For groups that need a lot of space, we recommend this gorgeous 5-bedroom home in Oak Bluffs. You can walk to the beach and town, rock on the breezy front porch with a beverage, or entertain in the back yard. For something cozier, we love this cozy 2-bedroom cottage.
More fun things to do on Martha’s Vineyard
Scope out the Lighthouses
There are 5 lighthouses on the island and the 4th graders at local schools spend a unit learning about and visiting them all! Learn more about all of the lighthouses here.
2. Visit the clay cliffs at Aquinnah
The Aquinnah Cliffs & Lighthouse is on the far western tip of the island. These red clay cliffs are a sight to behold! Definitely check out the lighthouse while you are there, which was recently moved inland a few feet to save it from tumbling off the cliff due to erosion.
3. Be a Pirate
4. Stroll through Edgartown Village
Be sure to scope out Historical Edgartown Whaling Village and travel back in time by strolling along the brick sidewalks of Edgartown Village. See the homes of former whaling captains, lush gardens, and dozens of notable sailboats and yachts dotting the harbor. (Be sure to stop into Island Outfitters on Main Street for a nice assortment of my jewelry. They sell really cute dresses and have a necklace to go with each one!)
5. Browse locally made art at the Vineyard Artisans Festival
6. Explore the Fishing Village Menemsha
Menemsha Fishing Village in Chilmark is a quaint working fishing village off the beaten path up island in Chilmark. We love to stroll along the docks and check out the day's catch. We always eat at the Galley-- save room for soft serve!
Don’t Miss: Oak Bluffs!
Oak Bluffs Restaurants & Things to Do
Also, don’t miss Gingerbread Cottages in Oak Bluffs! It’s a community of brightly colored campground cottages, right out of a storybook. Behind our shop and studio, this historical community first began as a circle of tents pitched in the summertime to worship. The Tabernacle, at the center of the community, is a large open performance and gathering space where we enjoy seeing live music during the summer as well as smaller, community-oriented events like a kid's art show and my daughter's string instrument performance.
For a healthy snack, stop into Juice by the Sea right by the harbor in Oak Bluffs. This little gem offers so much more than juice. You’ll find coffee, sweet treats, vegan dishes, great food and more. It is a place where you can find food that nourishes your body, and a staff that is passionate about healthy food.
2. Visit our Stefanie Wolf Designs Store in Oak Bluffs
Of course, please be sure to visit our new shop full of handmade, colorful, and island-inspired jewelry. We’d be so grateful to see your face and get to know you in person!
If you can’t visit our studio and shop in Oak Bluffs, don’t worry! You can see our full collection of Martha’s Vineyard-inspired jewelry online.