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Insights: Martha's Vineyard in 36 Hours & 3 Towns...

Updated: Jul 22, 2020

During the 45-minute ferry ride...stress disappears with each marker across the 7 mile sound.

Intrigued and daunted by the prospect of leaving the mainland for a few days? Martha's Vineyard is a charming 10 mile by 25 mile island off Cape Cod with a "relaxed luxury" vibe. Established in the mid-1600s by Thomas Mayhew Jr., whaling was a primary industry and brought prosperity to the island that can still be seen in the historic Captain's homes along Water Street in Edgartown. Well-heeled politicians like the Kennedys, Clintons & Obamas, musicians like James Taylor and Carly Simon, and TV & film stars like David Letterman, Spike Lee & Meg Ryan may arrive on their Gulfstream or Cessna, but they often trade their Gucci loafers for flip flops and their Tessla's for old Jeeps. Martha's Vineyard is much about "labels on the inside" vs. "labels on the outside".

There is something special about making the extra effort to get to Martha's Vineyard. During the 45-minute Steamship Authority ferry ride from Woods Hole to Vineyard Haven or Oak Bluffs, stress disappears with each marker across the 7 mile sound. Before you hop aboard the ferry, grab coffee and breakfast treats in Woods Hole at Pie in the Sky bakery, or fresh fish tacos and a margarita to go from Quick's Hole Tavern & Taqueria.

Wooden Boats and Black Dogs

Arguably Vineyard Haven's most famous business is The Black Dog Tavern. Started in 1969 in a modest harbor front shingled building, The Black Dog Tavern is said to be the Vineyard's first year-round restaurant and created from the vision of Captain Bob Douglas and named after his trusted companion -- his black dog. The Black Dog Tavern's legendary t-shirts can be seen on loyalists and patrons from Australia to Iceland and Los Angeles to Bali. In addition to merchandise galore, you can still grab a solid breakfast at the tavern and look out at the sloops in the harbor.

Vineyard Haven is Martha's Vineyard's year round port and is a working harbor. Main Street is dotted with unique, independently owned shops, and boat building is still going strong here. Wooden sailboats like Catboats, Ketches, and Schooners are still passionately and expertly crafted in the harbor side boatyards like Gannon & Benjamin Marine Railway.

Grab your catch of the day and enjoy dinner on a picnic table watching the sunset. The Net Result is a upscale fish market/takeout seafood spot serving locally caught seafood. Bring your own bottle of wine, take out a steamed lobster and stuffed quahog (pronounced "Ko-Hog") and cherish that picnic table and sunset. And if you cannot devour enough fresh seafood during your visit, The Net Result will ship to your home in the US.

Gingerbread Houses and Flying Horses

Next stop...Oak Bluffs! Well described as more high-spirited than haute, Oak Bluffs is home to a lively harbor scene, many bars and shops on Circuit Ave (i.e., the town's Main Street), and a stunning grass park overlooking Nantucket Sound (come fly a kite here).

Officially known as Cottage City in the late 1800s, Oak Bluffs was historically designed as a town for tourism and was built around the country's first summer religious camp, the Martha's Vineyard Camp Meeting Association. Methodist summer dwellers initially pitched tents, which evolved to tents on platforms, which evolved to over 300 colorful "gingerbread" cottages in the "campground" around the central Tabernacle church. During non-Covid times, you can still enjoy Community Sing on most summer Wednesday nights. Most of these "gingerbread houses" are impeccably restored and have been declared National Historic Landmarks.

One of the Vineyard's best value is a $3.50 ride on the Flying Horses Carousel. Located in the red building smack in the middle of town, the Flying Horses is the nation's oldest platform carousel and dates from the late 1880s. Sitting on a stationary wooden horse with carved features, manes of real horse hair, and glass eyes, grab a steel ring after each pass by the carousel conductor and look for the final brass ring, which earns you a free ride.

Back Door Donuts...Not Just For Late Nights After the Bars

Back in the day, perhaps after a few beers, patrons would empty out of the Circuit Avenue bars with the munchies. Right around 11:00 at night, the nearby bakery would begin their overnight shift baking donuts and apple fritters for the morning rush. Walk down the alley, knock on the bakery's back door, and Dave the baker would sell you a hot donut to satisfy your munchies.

Decades later the tradition is alive and well at Back Door Donuts. Thankfully now, you do not have to wait until the middle of the night, Dave has since retired (Raffi is now the donut master), and the donuts and fritters are just as good as they were 30 years ago. Insider's tip: arrive early if you want to guarantee a bag of apple fritters. On a splendid summer night, demand is high and supply can run out. Don't miss out!

Jaw's Bridge..."You'll Never Go in the Water Again"

As you head along State Beach from Oak Bluffs to Edgartown, you will pass over Jaw's Bridge. In 1975 we watched a great white shark grab hold of a swimmer's leg, terrorizing anyone who ventured into the sea to swim that summer. Now you cannot miss Jaw's Bridge by the vast numbers of swimmers jumping (voluntarily!) off the bridge and into the water below, bringing hours of entertainment. Some will perfect their back flip, some will belly flop, some will shriek as they make the 10' plummet, some will hold hands, and most jumpers will mark this accomplishment as a cherished right of passage.

Some More of our Favorites in Oak Bluffs

There is just too much to recap in one blog post. Here are some more winners:

Offshore Ale Company serves Martha's Vineyard year round with their own brews like Menemsha Creek Pale Ale and Lazy Frog IPA and serves up delicious food and very generous portions. Make sure you order their house cut french fries...made the REAL way.

Nomans is the brain child of Nancy's Snack Bar owner and is THE place for outdoor casual dining. Fresh food, well priced, good drinks, and picnic tables to sit and recap your summer day.

Dos Mas serves up the island's best street tacos on homemade hand-pressed tortillas. Their margaritas are freshly juiced and their homemade salsas pack a punch.

Ben & Bill's Chocolate Emporium is our go-to for ice cream in Oak Bluffs. With some crazy flavors like Lobster (yes, with real lobster bits) and Grape Nut, even ice cream purists will be content with at least one of the nearly 50 flavors.

Vineyard Vines and Widows Walks

There may be a reason why the Kennedys and the Obamas have gravitated to Edgartown. Described by Vogue magazine as "like the Hamptons without the crowds", Edgartown is full of New England charm and pristine historic homes, along with a ton of great shopping and dining.

Turn left or right down any street off Main Street, and you will see perfectly manicured hydrangeas, shingled homes, cobble-stone driveways, and a glimpse into the days of Moby Dick and the prosperous whaling industry. Look to the roofs of many of the large Captain's homes for their Widow's Walk, where legend is that wives would pace the rooftop looking for their husband's return from sea; while some husbands never returned from their whaling trips.

In 2005 two brothers launched their tie business in Edgartown and called it Vineyard Vines. Visit their flagship store, sit in "the boat", sip a complimentary Poland Springs water, and purchase some merchandise that is only produced and branded for Edgartown.

Looking to stay longer? Our favorite full service hotel is the Harbor View Hotel. Sitting at the end of Water Street, overlooking the Edgartown Lighthouse, two beaches, and the Chappaquiddick Beach Club, this hotel is great for couples in the Main House and families in their Captain's Cottages. Ask your Elli Travel advisor about the extra perks our clients receive.

Walk a few blocks from the Harbor View back toward Main Street and you will pass Chesca's Restaurant. Known for thick and rich New England Clam Chowder (the "white" chowder) and freshly caught seafood, scoring a reservation here can be tricky if you do not plan ahead. At the very least make sure you grab a drink and sit on the porch's white rocking chairs and watch the world pass by.

More Favorites in Edgartown

The Scoop Shack on Dock Street is our favorite Edgartown ice cream shop, serving small batch homemade ice cream with only the best ingredients. As our daughters say, "Count your blessings, not your calories!".

The Right Fork Diner is located at the Katama Airfield and makes delicious breakfast and legendary Eggs Benedict.

Morning Glory Farm has been a working farm since 1975. Their farm stand sells island grown lettuces, carrots, squash, and home made pies, breads, & muffins.

Katama General Store makes fresh breakfast sandwiches and lunch sandwiches and is located on the way to South Beach. It is also a go-to for some of MVY's best iced-coffee.

With first hand insight and strong travel partners, contact your Elli Travel Advisor or email to book your next get away.

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