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On the Road Again: Martha’s Vineyard

Black Dog Tavern, Martha’s Vineyard. Photo Deborah Loeb Bohren.


Story & photos by Deborah Loeb Bohren

Vaccinated and ready to hit the road again — but where?  I found after being housebound with the rest of the world for more than a year, I was uncharacteristically and unexpectedly nervous about venturing out. So, where to go? I was okay with airplanes but not airports; a ten-day quarantine didn’t work for a two-week trip; and what were the local Covid protocols, vaccination rates and heaven-forbid access to health care should I need it when I got wherever it was I decided to go?  My mind was swirling but, as it turns out, I didn’t have to go far.


Oak Bluffs Fishing Pier. Photo Deborah Loeb Bohren.

The answer was a trip to Martha’s Vineyard. It had been on my radar for a long time, but pre-Covid, it felt too close, and not exotic enough when I could go to the likes of Paris or Namibia (my last pre-pandemic trip).  Now it ticked off my post-quarantine boxes and thus the perfect place to get back my travel groove.

The Vineyard is easily accessible via ferry, car ferry or plane depending on your starting point. Coming from Connecticut, I chose to drive to the Seastreak Fast Ferry out of New Bedford, Massachusetts. The ferry terminal is right off the highway with a large parking lot or valet service if you prefer — and queuing up under beautiful blue skies to board was much less stressful and more fun than airport security lines. I felt liberated, energized and unbound.


Summercamp Hotel, Oak Bluffs. Photo Deborah Loeb Bohren.

In a quick 50 minutes (less time than it takes me to take the train to New York City), I was off the ferry and walking down Lake Avenue in Oak Bluffs to Summercamp Hotel. The hotel has a fun, energized island vibe, and is intended to re-create that feeling we had in our youth during summer camp. There is a little red wagon in the lobby filled with toys to appeal to children of all ages, a larger than life-sized game of Connect Four on the wall, and decor throughout reminiscent of your favorite camp activities (think archery, canoeing, fishing off a dock). The hotel caters to all: singles, couples and families, and is dog friendly too (sorry Indy, I promise I will bring you next time!). The long, wide porch overlooking the harbor complete with rocking chairs was the prefect place to unwind each evening before or after dinner.

I learned that there are six towns on the island, each with its own personality.

Gingerbread Houses in Oak Bluffs. Photo Deborah Loeb Bohren.


Oak Bluffs, funky, casual and friendly. The town traces its’ roots to the Methodist camp meeting movement of the 19th century and the 34-acre Martha’s Vineyard Camp Meeting Association in the center of town is still a vibrant community of just over 300 of the 500 original brightly colored Victorian-style gingerbread cottages. The Flying Horses Carousel is the oldest platform carousel in America, another of the town’s claim to fame.


Classic Edgartown Architecture. Photo Deborah Loeb Bohren.

Edgartown, pristine, upscale and manicured. If Oak Bluffs is about gingerbread houses, Edgartown is about stately white Greek Revival homes, art galleries and the bridge made famous by Stephen Spielberg’s JAWS. There’s also the requisite lighthouse and it is the gateway to Chappaquiddick.


Nat Benjamin, Founder Gannon & Benjamin Marine Railway. Photo Deborah Loeb Bohren.


Vineyard Haven, year-round main ferry port, working harbor village. The town boasts a Cultural District, shipyards and The Martha’s Vineyard Museum. The island’s infamous Black Dog Tavern started here and is still a must for breakfast, lunch or dinner and iconic Black Dog merchandise. It is also home to Gannon & Benjamin Marine Railway, boat designers, builders and restorers of wooden boats extraordinaire.


Aquinnah Lighthouse. Photo Deborah Loeb Bohren.


Aquinnah, the western most town, red clay cliffs, pitch perfect sunsets. Less town than location, the red brick Aquinnah Lighthouse and adjacent National Historic Landmark red clay cliffs that dramatically drop down to the beautiful Moshup beach, make for an idyllic afternoon.


Best Lobster Roll Ever at Larsen’s Fish Market.Photo Deborah Loeb Bohren.


Chilmark, rolling hills, long stone walls, nature preserves, dramatic coastlines. The picture postcard fishing village of Menemsha is found here and the main activity is fishing and eating fresh just off-the-boat seafood. Larsen’s Fish Market, another island institution and a destination in itself, serves up the freshest of steamers and local oysters, amazing lobster rolls where the lobster and not the bread is star, and sublime clam chowder. It’s take out only and I’m convinced finding a spot on the adjacent beach, rocks or makeshift crates along the wharf to eat only adds to the already memorable meal.

West Tisbury, rural charm, home to the historic Grange Hall. The area is more a drive through as you explore the island, but the lovely drive and fan favorite general store shouldn’t be missed.


Moshup Beach and Clay Cliffs. Photo Deborah Loeb Bohren.

Oak Bluffs was my base because for a first-timer it offered everything I needed — lots of restaurants, local beaches and easy access to the rest of the island. From there you can bike or take the local #13 bus to check out Edgartown or Vineyard Haven. You do need a car to explore further afield. I rented one for a couple of days to check out Aquinnah, Menemsha, and the likes of Lobsterville Beach, Squibnocket Pond, and Lucy Vincent Beach (off season access only for visitors), along with just about every road on the island in between.


East Chop Lighthouse. Photo Deborah Loeb Bohren.

A visit to the island’s several lighthouses is mandatory and like the towns they guard, they each boast a different persona. Visit East Chop in Oak Bluffs for sunrise, Aquinnah for sunset and Edgartown Light anytime.


Taps at Bad Martha Brewery. Photo Deborah Loeb Bohren.


Perfect for an afternoon stop after a day at the beach, a rainy day activity, or let’s face it whenever you are thirsty, is Bad Martha Farmer’s Brewery & Tasting Room in Edgartown. Complete with a fish tale (or rather a mermaid’s tale) and using grape leaves harvested on the island to make their beer, they offer a rotating selection of up to 10 different beers daily. Our tasting included all manner of ales — summer, pale and IPAs — a Turkish Coffee Porter, Oyster Stout, a hard cranberry seltzer and, of course, a brew appropriately named Mischievous Mermaid. Cheese, charcuterie and pizzas with toppings like bacon soaked in beer, along with outdoor games and some cool Bad Martha swag, round out the experience.


Edgartown Homage to Jaws. Photo Deborah Loeb Bohren.

Ice cream seems to be an island essential at any time of the day or night, with what seemed like a disproportionate number of homemade options in Oak Bluffs.  I tried to be objective, trying the same flavor at each and, hands down the winner for me was Ben and Bill’s Chocolate Emporium.  They offer unique, intense, inventive flavors ranging from Cotton Candy and KGB (think Kaluha, Grand Marnier and Baileys all rolled into one scoop) to Lobster and Sea Salt Caramel, all of which were wonderfully smooth and creamy.

Local seafood prevails at restaurants, with lots of outdoor seating options along the island’s many wharfs. For those without, I appreciated that they made a point of telling you that their staff had been vaccinated in this new post-pandemic environment. If you are not in the mood for seafood, not to worry, it was easy to find delicious alternatives from pizza by the slice to upscale farm to table options all across the island and for every taste and budget.


Back Door Donuts. Photo Deborah Loeb Bohren.

If you crave dessert or a late night snack, literally follow your nose to the literal back door of Back Door Donuts, aka Donuts After Dark, for mouth-watering apple fritters or double chocolate, maple bacon or Boston cream donuts, to name a few. It feels a little illicit as you line up with your fellow travelers and residents in an off-the-beaten path parking lot as the sun sets while they fry up your order, but that’s all part of the fun. All that was missing was a secret knock.


Photographer Alison Shaw in her gallery. Photo Deborah Loeb Bohren.

Like any good island destination, there is a plethora of shopping, from the requisite kitschy vacation t-shirts and salt water taffy to exquisite hand blown glass by the artisans at The Martha’s Vineyard Glassworks.  For a true memento of your time on island, head to the Alison Shaw Gallery in Oak Bluffs Art District. Alison’s photographs capture the heart and soul of Martha’s Vineyard from sunrise to sunset, up island and down, as only she can.


Edgartown Lighthouse. Photo Deborah Loeb Bohren.

Martha’s Vineyard may be best known for beautiful beaches, fishing, great seafood and a laid back vibe. And it has all that and then some. But what struck me from the moment I arrived and what made this a truly special trip was how friendly everyone was. I’m not just talking about waiters providing perfunctory smiles and good service. I mean everyone, everywhere, all the time: walking down the street strangers would make eye contact and say hello; hotel and restaurant staff didn’t simply take your order or check you in — they would ask what you were thinking of doing, give you tips, ask where you were from and before you know it you are sharing your love of dogs and dog stories with the barista making your latte (I have a Havanese, she has a Boston Terrier).


Sunset from the porch at Summercamp. Photo Deborah Loeb Bohren.

Sitting on the porch at Summercamp guests, from as close as Boston and as far away as Sweden, shared stories, recommendations and even their wine with one another striking up friendships. The conversations were organic, natural and real. I’m not sure if it’s the air on the Vineyard or a small silver lining of finally being around people after more than a year in quarantine. Regardless, it’s what took the Vineyard from a fun place to hang out for a week to a must go — and must go back again — place for me.


Deborah Loeb Bohren is a fine art and travel photographer. Photography has been Deb’s passion since her father put a camera in her hand when she was only five years old. Today she combines that passion with her love of travel, using her camera to capture the intersection and interplay of light, line and color to create visual stories from the flea markets of Paris to the dunes of Morocco and from Machu Picchu to Havana and beyond. She lives in New York.

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