Martha’s Vineyard…A Classy Island with a Rich History!

Now that the snow has melted and things have heated up, it’s finally time to highlight one of our most favorite stateside getaways…Martha’s Vineyard! Martha’s Vineyard is a true island located approximately 7 miles just south of Cape Cod, in Massachusetts. It is only accessible via ferry or air, there are no tunnels or roadways connecting it to the mainland. It’s approximately 96 square miles, triangular in shape, 25 miles at its longest point east to west and 9 miles at the longest point north to south. While the island receives visitors year round, we were there during the month of August and the weather was mild to hot.


Getting there

There are direct flights available to Martha’s Vineyard from the Boston Logan Airport. However, we opted to fly into Boston, rented a small SUV (you can also take a train, bus, or car service), and made the one and a half hour drive down to Woods Hole/Cape Cod to ride the ferry. Year round ferry service via the Steamship Authority Ferry to Martha’s Vineyard provides transportation for both vehicles and passengers. However, if you have a vehicle, you will need call ahead to make a reservation. If you are just traveling as a passenger (without a vehicle), no advance reservation is necessary. If you are traveling between May and October, passenger service is also available via ferry from various points in Massachusetts (Hyannis, New Bedford, Falmouth, Nantucket), New York City, Highlands/New Jersey, and Quonset/Rhode Island.(

If you opt to fly directly into Martha’s Vineyard, rental vehicles are also available on the island, but be sure to make your reservation well in advance as inventory is limited.

Where to Stay

Martha’s Vineyard continues to maintain the simplicity of island living. There are no chain hotels or resorts lined along the water, however there are more than 80 lodging options (luxury hotels, bed and breakfasts, inns, Airbnbs, etc). We opted for a home via Airbnb, located a little over a mile from downtown Oak Bluffs/Circuit Ave.

Where to eat

As you can imagine, there are numerous good eateries on Martha’s Vineyard. While the island offers several options for breakfast, The Black Dog Tavern for us was a must visit given its history and back story about an Air Force pilot named Robert Douglas and his dog (visit their website to learn more: While this cozy restaurant sits directly on the water in Vineyard Haven, there are other eateries that fall under the Black Dog umbrella as well (Bakery Cafe, Heights Cafe, Water St. Bakery, and Dockside Cafe).

Looking for a great burger? If so, then Fat Ronnie’s is a must try! Not a beef eater? No problem…the lobster roll and turkey burger are just as good! Located in Oak Bluffs, Fat Ronnie’s is a small, efficient spot where you can pull up to one of their high top tables and shamelessly indulge!

It’s clear we’re in lobster country! So many of the restaurants on Martha’s Vineyard feature lobster cooked in various ways, and Lookout Tavern is yet another option for a great lobster roll (make sure to order it warm!). Don’t believe us? Well, they were voted best Lobster roll in Martha’s Vineyard 7 years in a row (2012-2018)!

Or, if by some miraculous reason you’re tired of lobster, you can pick any number of delights from their wide menu selection. Here you will find salads, sandwiches, tacos, burgers, and even sushi! Also located in Oak Bluffs, Lookout Tavern features both indoor and outdoor seating with unobstructed views of Nantucket Sound.

Italian anyone? Girodano’s is your place for a good slice of pizza or authentic Italian food! Founded in 1930, this island gem is known for it’s pizza, chicken parmesan, pasta and clam bar. There’s a reason they consistently win Best Pizza on Martha’s Vineyard..It’s a staple on the island and the good food keeps people coming back!

Looking for more of a fine dining experience? Atria (located in Edgartown, just a quick 15 minute drive from Oak Bluffs) is a great choice! Although the menu changes nightly, the food is both Mediterranean and Asian inspired and is grown locally on New England farms. The restaurant is a home that has been converted into an incredibly inviting restaurant and bar. The outside space is decorated with hanging lights, and has several seating areas. The wine list is impeccable and while parking is somewhat limited, you won’t be disappointed!

If it’s early evening and you happen to see a long line of people waiting patiently in what appears to be a parking lot, then chances are you’ve happened upon Back Door Donuts. Located in the rear of the Reliable Supermarket, identified only by its small sign and famous purple door, this quaint little shop is definitely on the list of “must try’s” on Martha’s Vineyard. Their donuts are made to order and as evidenced by the long lines, are a definite fan favorite!

Things to do:

The Flying Horses, the oldest continuously operating carousel in the nation, is located at the beginning of Circuit Avenue in Oak Bluffs. It was built in 1876 and the horses are hand carved with real horse hair tails and tiny lead animals embedded in their glass eyes. The Flying Horses was listed on the National Register of Historic Places in 1979 and designated as a National Historic Landmark in 1987.

Sunset at Menemsha (Chilmark)

Ever experience a magical sunset that literally transforms into the most vivid art canvas ever imagined?  The ultimate way to get grounded with nature, family, and friends is to trek over to Menemsha (in the town of Chilmark), for an unforgettable evening witnessing nature’s finest artist at work.  The best time to arrive is at least 2 hours before the forecasted sunset.  Pack a picnic basket, cooler of your favorite eats and drinks, small portable speaker, blanket/beach chair, and camera to enjoy this spectacular show.  While there are several food stands and fish markets on and near the beach to purchase fresh seafood fare, Homeport is the only in house dining restaurant overlooking the harbor.

NOTE…Parking is limited and only available for two hours.  We suggest utilizing the shuttle service (running every 10 minutes) from the off-site parking area on Tabor Road.  This shuttle is run and operated by the VTA city bus service and the lot holds only about 70 cars.  The drive from Oak Bluffs is 14 miles and takes about 30 minutes on windy, no shoulder roads.  The least expensive way to Menemsha is by bus, or should we say 3 buses…and takes 2 hours, in case you’re interested.  A third option is by ride share, estimating $40-$70 depending on car type and availability.

Martha’s Vineyard Museum

You definitely don’t want to miss out on a visit to the Martha’s Vineyard Museum as it brings together the island’s rich history, art and culture. The Museum does a great job of quickly but thoroughly educating it’s visitors as to the indigenous Wampanoag people, colonization by the English, origins of Martha’s Vineyard own sign language, and how the island quickly became known as a resort for the wealthy, former Presidents, and African American Elite.

African American Heritage Trail

Take some time to learn about the 30 different stops on the African American Heritage Trail. Each location celebrates the previously undocumented contributions, history and culture of African Americans. Stops along the trail include everything from gospel churches to the first African American owned guest house on Martha’s Vineyard featured in the original Green Book (as referenced in the Academy Award winning movie.) The tour options range from 1.5 to 4.5 hours at a cost of $35 to $75.

Visit for more details.


There are no shopping malls on the Vineyard. However, each town has its own strip of boutiques and galleries, providing their own unique finds. However, if you’re in Oak Bluffs or Edgartown, Circuit Avenue and Main Street respectively, are where you’ll want to be!

Beach/bridge jumping:

Interesting Fact….the movie Jaws was filmed on Martha’s Vineyard back in 1975. The American Legion Memorial bridge from the film is still an infamous landmark and also serves as the dividing line between Edgartown and Oak Bluffs. As you approach the bridge you’re bound to see groups of people waiting in line to jump into the water, completely ignoring the “No Jumping or Diving from Bridge” sign. Many visitors feel a trip to the Vineyard would not be complete without indulging and everyone knows this is a perfectly acceptable thing to do when on the Vineyard. So while we’re not here to judge, we would like to advise you to not go at low tide as the water is quite shallow. Also, you’ll want to be extra careful when scaling the surrounding rocks as many are often covered in seaweed, making them very slippery.

Finally, Martha’s Vineyard is and continues to be an enticing, unique, island destination. While you have all the creature comforts of home, it’s a perfect balance of the old and new. It’s simple, yet rich history, along with it’s affluent reputation, makes it an experience like no other!


  •  There are plenty of grocery and convenience stores, as well as lots of places for take-out, sandwiches, etc.
  • Many of the businesses on the island are only open during peak season (May to September)…be sure to check ahead before planning your trip!
  • Martha’s Vineyard hosts the Striped Bass and Bluefish Derby every year (one of the oldest, most prestigious fishing tournaments in the country)! The island often hosts over 2,000 people just for this even alone!
  • The African American Film Festival is held every August on Martha’s Vineyard. This festival is currently in its 17th year and showcases some of the greatest emerging Feature, Documentary and Short films produced by and starring African Americans all over the world.
  • The Grand Illumination is a tradition created as a way to welcome the Governor of Massachusetts to Martha’s Vineyard where lighted lanterns are lit and hung on the porch of the very famous gingerbread cottages. This is another annual event which occurs every third Wednesday in August.
  • Martha’s Vineyard attracts many affluent visitors each year. President Barack Obama, President Bill Clinton, David Letterman, Meg Ryan, Michael J Fox and Spike Lee have all been seen vacationing on the island.

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