A Presidential Retreat – Martha’s Vineyard

In the 19th century Martha’s Vineyard was an epicenter of the American whaling industry, sending thousands of whalers off on their ships from the port in Edgartown (for more on the subject, see Whaling on Martha’s Vineyard by Thomas Dresser). In prior years Presidents like Ulysses S. Grant and Grover Cleveland had made trips to the island for relaxation (Boston Magazine), and then in the sixties the Kennedys brought renewed interest to Martha’s Vineyard as one of their main vacation spots (Jackie Kennedy owned a home there). Since then, the Clintons and the Obamas have vacationed and purchased homes there as well. Vacation homes sell for millions of dollars and celebrities joined in, making the island a hub for the wealthy and well-connected (Business Insider). I however, am not a U.S. President or a celebrity. As I embarked on my first visit to Martha’s Vineyard I had to ask myself, would I get a taste of what it was that drove them to Martha Vineyard’s shores?

One thing that seemed an evident lure was seclusion. It is an island about 93 square miles (map), consists mostly of forested conservation land rimmed by beaches and can only be accessed by ferry boat. There is plenty of space to spread out and hide at the same time. The atmosphere is laid back and privacy is respected. What may have changed over the years is the number of people who visit the island. According to the Martha Vineyard Chamber of Commerce, the population of about 17,000 all-year residents swells to nearly 200,000 in the summer months. Fortunately for the Presidents’ need for privacy, the crowd seems to gather mostly around the coastal towns of Oak Bluffs and Edgartown. Since we didn’t have an island mansion to hide in, how would we manage the crowds?

We had one trick up our sleeves – we planned our vacation for September, weeks after the school year had begun. The weather was still around 70 degrees Fahrenheit, and the summer crowds for the most part were gone. It did get a tad bit cooler in the mornings and evenings, but nothing a cute hoodie from Soft as a Grape [14 Circuit Avenue, (508) 696-6800] couldn’t take care of. There were no lines for bike rentals, and no reservations needed for anywhere we wanted to eat. We even got a room at the famous Wesley Hotel at a discounted rate.

On our first day the ferry from the Steamship Authority dropped us off at Oak Bluffs in the early afternoon and we headed for the nearby Wesley Hotel, now renamed the Summer Camp Hotel. The hotel was built by A.G. Wesley in 1879. The hotel suffered a fire in 1894 that Wesley himself started and went to jail for. In 1986 it was remodeled and is a pleasant place to stay with cozy rooms furnished to make you feel like you are staying in an old country inn, complete with wooden floors that squeak under the carpet in the hall, and rocking chairs on a large front porch.

Our first order of business was to take the Martha’s Vineyard bus tour to get a sense of the island. 

Martha’s Vineyard Tour Bus

As we drove by the waving green grasses that tickled the ocean’s horizon, it made it hard to stay on the bus and listen to the driver’s historical tidbits when I wanted to be outside exploring. I was told that the island was named after the daughter – Martha – of the British explorer Bartholomew Gosnold, who visited the island in 1602. In any case, that is what is commonly believed.

A pier in Oak Bluffs


The island was much bigger than I thought. The tour to Edgartown and back took the entire afternoon, which included a stop in Edgartown where we could get off the bus and roam around. We shopped at the Black Dog general store [11 Main Street, (508) 627-6412] and got chocolate fudge to go at Murdick’s Fudge [21 North Water Street, (508) 627-8047] before getting back on the bus to return to Oak Bluffs. We changed at the hotel and had an amazing dinner at the Offshore Ale Co. [30 Kennebec Avenue, (508) 693-2626). Voted the best Bar/Pub by Martha’s Vineyard Magazine in 2020, it has a wood paneled, somewhat nautical pub-like feel and was crowded with local residents enjoying a Friday night when we were there. A place to go in jeans and a sweater and dine on excellent seafood. We had big pints of dark amber beer, oysters on the half shell, and Portuguese fish stew with slices of crusty bread for dunking.

            The next day after breakfast at the hotel we took walks along the beach.  It had cooled off and clouded up a bit, and it was windy.  The grasses swayed and the surf raged. 

Surf at Oak Bluffs

There was no one on the beach, and I sat huddled in my sweatshirt. “Come on, let’s get a nice big hot breakfast” my friend said. The best place to do that was at nearby Biscuit [26 Lake Avenue, (508) 693-2033]. We got a table by the window and ordered plates of, yes, biscuits, with cream sausage gravy and scrambled eggs. There were maybe three or four other tables that were seated, otherwise it was quiet. We asked the waitress if it was always this quiet in the morning, and she said “Please! In the summer there is a line out the door every day! You came at a good time.” We felt pleased with ourselves, but that feeling was soon overcome by guilt at having consumed about 2,000 calories at breakfast. We needed to work it off, so we went on a walk through the Gingerbread houses.

Gingerbread Houses

The story of the Gingerbread Houses began when the first Methodists camped in tents in this area where services were being held. They returned to the same spot year after year, and eventually the tents became more permanent wooden homes, with varying “gingerbread” architecture to distinguish the different families. They are restored and lovingly maintained by their current owners, and the charming neighborhood makes for a nice place to saunter.

Gingerbread Houses

With more energy to burn, we decided to rent bikes and ride along the coast to the bridge between Edgartown and Oak Bluffs, one of the locations where they filmed the classic movie Jaws. It didn’t seem like too long of a distance, but what I didn’t calculate with is how difficult it is to steer a bike in the strong wind that had started. As I peddled slowly along I struggled to keep the handlebars straight as the wind beat upon my front wheel….I didn’t get very far before I called out to my friend that I’d had enough! So, we never made it to the bridge, but hopefully more successful bike rides on the island are in my future. There are many biking and walking trails all over the island of various lengths (bike trail maps).

Dinner that night was memorable at the Lookout Tavern [8 Seaview Avenue Extension, (508) 696-9844]. We sat on the side where the windows look out over Nantucket Sound just as the sun was setting while we sipped our wine. Once it got dark, there wasn’t that much of a view, so we moved to a table inside and feasted on their lobster pot, which included the typical sides of sausage, corn and potatoes and a good value.

East Chop Lighthouse

On our last day we started off with a quaint breakfast at Linda Jean’s [25 Circuit Avenue, (508) 693-4093], a diner full of local atmosphere, where the waitresses seemed to know everyone by name. Then we wanted to tuck in a little more sightseeing before catching our ferry at 2pm, so we headed out to the nearby East Chop Lighthouse, one of several on the island, and took a few more pictures despite it being a cloudy day.

East Chop Lighthouse

There was still some shopping to do down Circuit Avenue, like at Vineyard Vines [56 Narragansett Avenue, (508) 687-9841] where I got a cute pink baseball cap. A must-do stop to share a cup of ice cream is Mad Martha’s [12 Circuit Avenue, (508) 693-9151) where the Obamas are known to get their ice cream fix. Before we knew it, it was time to rush and get some lunch at Nancy’s [29 Lake Avenue on the harbor, (508) 693-0006] before we caught our ferry.

Sitting on the dock, looking out over the deep blue waters of the sound as I enjoyed my fish and chips, I mused over our trip and asked myself – did I feel at all a bit Presidential? I think sitting there, I did. President Obama had in fact eaten lunch at Nancy’s, there were pictures of it all over the walls. Perhaps he had sat in the very seat where I now was, so why not feel that way? As we walked towards the dock after lunch, I was overcome with a feeling of not wanting to leave. I mused about maybe buying a place out here one day. For a moment, is seemed entirely possible. Perhaps some of the Presidential powers had rubbed off on me after all….anything seemed possible.

Top Ten Places of Interest

  1. Oak Bluffs
  2. Edgartown
  3. Gingerbread Houses
  4. Summer Camp Hotel
  5. Bus tours
  6. Biking and walking trails
  7. Chappaquiddick
  8. Public beaches
  9. Lighthouses
  10. Fishing Charters

Date trip taken: September 2015

Published by Irena Springer

I am a travel blogger who loves to make the most out of each and every trip.

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