Insider’s Tips to Martha’s Vineyard

Are you visiting Marthas’ Vineyard for the first time? Below is a list of “Insider Tips” for things to see and do on island!


When I have a visitor from out of town, the first place they want to see is the Gingerbread Cottages in Oak Bluffs, but I also take them to The Gay Head Lighthouse – for a more local, authentic experience. Although the cottages are a fantastic experience, with colorful cottages scattered around the campgrounds, the Gay Head Lighthouse is a sight to be seen, specially during sunset.

When I want to escape the crowds/tourists, my favorite place to visit is anywhere “up-island”. The island is referred to as anywhere up or down island, with the down island towns to be the most populated. When you want to escape the crowds, head anywhere up island: Chilmark, Aquinnah, or West Tisbury for some amazing sightseeing without the massive crowds.

If this is a romantic trip, I recommend Menemsha Beach for kissing with a view. Menemsha is THE place to bring a romantic picnic to! Grab a beach blanket and settle in to watch the most gorgeous sunset on island. So gorgeous, everyone claps and boats honk once it sets.

The best place to walk the dog is a 70-acre ‘dog park’ on the island.  Dogs are allowed to run free on the Land Bank Tradewinds Airport in Oak Bluffs, perfect for Fido to get its energy out!

Museums are wonderful, but if you are traveling with kids, you’ll want to visit the Flying Horses Carousel in Oak Bluffs. They are the oldest operating platform carousel in America – and if you grab the brass ring, you get a free ride!

New England Food:

If you are looking for typical New England cuisine, I recommend a variety of places! Grace Church in Vineyard Haven has amazing lobster rolls, the Wharf Pub in Edgartown boasts the best stuffed quahogs on island, and if you’re looking for awesome clam chowder, make sure to visit Chowder Company in Oak Bluffs. Craving lobster macaroni & cheese, head to the Atlantic in Edgartown – it’s more lobster than pasta!

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The best place to go for coffee & a breakfast treat depends on which town you’re at! Head to Espresso Love or Behind the Bookstore for great espresso-based drinks, or to Mocha Motts in Oak Bluffs for tasty baked goods to pair with your coffee. Black Dog Bakery In Vineyard Haven has the best slice of chocolate cake on island, so make sure to treat yourself.

Looking for cheap food on island? Grab the Tomato Bisque & Three Cheese Grilled Cheese at The Atlantic in Edgartown, a great deal! The Square Rigger in town also has a deal for less than $20, you get a lobster roll and a cup of clam chowder. Head to La Choza Burritos for the tastiest burritos you’ll try and leave with a burrito and drink for under $10.

If you find yourself in Edgartown, Atria is the spot for late night dining. Check out the Port Hunter as well for live music, and if you’re in Oak Bluffs, The Ritz always has great music and inexpensive but quality food!

For a luxurious meal if you’re on an expense account, stop in to Detente and make sure to order their Peach & Taleggio Salad. Head up island and make reservations at the Outermost Inn Restaurant for dinner with a view.

Seeing a lot of lighthouses? Martha’s Vineyard is best known for its lighthouses, gorgeous beaches, and the fact that the movie Jaws was filmed here!

When you come to Martha’s Vineyard, get your picture taken at each lighthouse! It’s the perfect way to tour the island by the lighthouses.

The best vantage points are taken by walking to the top of Gay Head Cliffs.


Menemsha offers great views and is the best place to watch or experience the best sunset of your life.

On Martha’s Vineyard, outdoor lovers will want to rent a bike and cruise around the bike trails all over the island, seeing the towns by bike. Head to Arrowhead Farm for some horseback riding – they even host a ladies night of horseback!

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Looking for a little exercise? Walk along any of the many beaches on island.

After a day of adventure, Sea Spa Salon is the best place to go for a spa treatment. Their attentions are top notch and their services are the best in the industry, plus the staff is always helpful and friendly.

If you are a museum lover, Edgartown’s best museum is the Martha’s Vineyard Museum, where you’ll learn about the island’s history, as well as whaling industry facts.

Looking for exciting night life? Go dancing at The Ritz, Loft, The Lampost or The Port Hunter for live music.

The MV Times will keep you posted on what’s happening all over the island! Published weekly, it prints an calendar section with all the island activities and is the perfect guide to guide your vacation.

You can tell a lot about Martha’s Vineyard from visiting and watching The MV Agricultural Fair, the Grand Illumination Night, and the food & wine festival events.

In the spring you should attend the Martha’s Vineyard Wine Festival, where over 500 wineries meet to share their wines. Private chef dinners hosted in local island homes, cocktail parties, and so much more.

In the summer you should attend The Taste of the Vineyard, a food event where island restaurants showcase the best of the best and everyone dresses up for the night!

Did you know that Martha’s Vineyard is known for their fall harvest festivals Plan a visit to the Morning Glory Farm in the fall for their annual pumpkin festival. Buy pumpkins for the home, watch them being catapulted into a field, and eat everything pumpkin-flavored!

Come to Martha’s Vineyard for Christmas in Edgartown in the winter. The town puts on a weekend of holiday for visitors and locals alike, where shops open up with great deals, restaurants offer delicious treats, and joy is all around.

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Insider Tip: Check out the often over-looked local farms on island. Most offer farm tours! The FARM Institute offers summer camps for the kiddos, but it’s also a great place to purchase local meats. Morning Glory Farm has some excellent salad bars for lunch – created with local produce, it’s a deliciously healthy farm meal. I’ll bet you didn’t know we also have local honey and locally roasted coffee, some of the best souvenirs.

Back on the mainland, you can visit the town of Falmouth and have lunch at Red’s at the Sea Crest Beach Hotel!

These insider tips to Martha’s Vineyard were written by Marnely Murray who pens Cooking with Books.

3 thoughts on “Insider’s Tips to Martha’s Vineyard”

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