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Six Marvelous Towns, and the Man that Knows All of Its History

Posted on June 23, 2023
A historic, black and white photo depicting a large hotel. A large "W" sit atop the hotel.
The historic Wesley House Hotel. It is now known as the Summercamp Hotel, in Oak Bluffs, MA.  Source | Martha's Vineyard Museum


Thomas Dresser, long time Martha’s Vineyard resident, wears many hats.  Historian, author and tour guide are just three of the many. Built Story is lucky to have worked with him the past couple of years! Below, we chat with him about Martha’s Vineyard, the stunning island – for its beauty, its history, and the people that call it home – that lies just off the coast of Massachusetts.

A Q&A with Thomas Dresser

Built Story ToursHi Tom! Tell us a little bit about yourself. When did you first discover Martha’s Vineyard?

A man, wearing a blue shirt stands.  Behind him is a street.
Dresser stands, with Seaview Avenue in Oak Bluffs, behind him. Photography | Thomas Dresser

Thomas Dresser: In 1995 I attended my 30th high school reunion in central Massachusetts.  A classmate who had moved down to Martha’s Vineyard after college, walked into the reunion hall the same time I did.  “Tommy, it’s the 90s,” Joyce said.  “A woman can buy a man a beer.” 

That was all it took.

She invited me down to the Vineyard for a weekend, and I’ve been here ever since.  We celebrate our 25th wedding anniversary next week.

Who knew that one event would change my life!

 BST: You are a very prolific writer.  More than 15 books on Martha’s Vineyard history alone. What has been your favorite book to write?

A picture of a book. Title is: "Mystery on the Vineyard", by Thomas Dresser
Mystery on the Vineyard, by Thomas Dresser

TD: It may sound like a cliche, but the first book I wrote for the History Press was my favorite.  It was a challenge to organize my thoughts into chapters and present the story in a readable format.  It was an unusual topic: an unsolved murder from decades ago. 

Mystery on the Vineyard has two intersecting themes: I describe the actual murder that occurred in June 1940, and why it went unsolved.  And I weave in my research and interviews to determine who the killer was and how the case was resolved.   

Mystery on the Vineyard was published in 2008, and still sells well after all these years.


BST:  With all of this extensive knowledge, you also offer Martha’s Vineyard tours. Some in-person, some self-guided. What is your favorite in-person tour that you take people on?

A busy harbor scene.  A boat is docked, people are walking about, shops in the background.
Oak Bluffs Marina. Photography | Jonathan Sherman

TD: Twice a week I offer walking tours of downtown Oak Bluffs to patrons of the Pequot Hotel.  And once a month I offer walking tours of the Oak Bluffs cemetery.  Both tours are a treat because I have a chance to share fun bits of info and answer questions from tourists.  It’s always a treat to present the Vineyard experience to newcomers. 

BST: Edgartown tours offer people a lively walk through historic brick buildings, beautiful vistas of the water, and streets humming with people and pretty shops. Your Ghosts of Edgartown Tour, though, also examines strange happenings that townspeople have observed over the centuries.  Which account of a spirit do you find the most odd?

A white two-story building, with an attic, stands.  Black shutters.  White picket fence in front.
A jail, located in Edgartown, MA. Photography | Thomas Dresser

TD: The Ghosts of Edgartown Tour includes an unusual experience at The Christopher hotel, a spirit in the hallway of Atria restaurant, but the strangest sounds are at the jail, from a mysterious typing to a faucet turned on and off is downright creepy.  Then we learn a presence was sighted on the security camera, although all the inmates were asleep in their cells, is other-worldly.  The ghosts are all around you!

BST: Oak Bluffs tours reveal a bustling beauty of Martha’s Vineyard. From shop- and restaurant-lined Circuit Avenue, to the iconic Ocean Park, to the wonderfully unique Gingerbread cottages. What can be expected from your (very newest!) Historic Oak Bluffs Self-Guided Walking Tour?

A black and white photo, historic.  A crowd of people, some with bicycles, stand in front of a one-story building with the sign "Flying Horses" on it.
Flying Horses Carousel, which still operates today, in Oak Bluffs, MA. Source | Martha's Vineyard Museum

TD: A century ago, Oak Bluffs hosted an amusement park atmosphere with a massive roller-skating rink, two bowling alleys and a couple of dance halls. Today remnants of the past stand among stalwart businesses and engaging activities of the present.  The Oak Bluffs tour is a blend of the past and present, in an engaging environment that welcomes everyone to the Island.

BST: Of all the things to do in Oak Bluffs, what would you most recommend to a new visitor?

Two quaint, two-story cottages stand. One is white, the other brown. American flags decorate the front yards.
Wesleyan Grove. Oak Bluffs, MA. Photography | Benjamin Rascoe

TD: If you’ve never meandered through Wesleyan Grove, I would make that a mandatory experience.  Although Methodist campgrounds were popular in the 19th century, Oak Bluffs is unique in offering easy access to check out the gingerbread cottages.  The charm of a walking tour is that the highlights can be pointed out on a short stroll.  Wesleyan Grove is a delightful experience of a unique little community.  It’s a treat to explore.

BST: Your Martha’s Vineyard Black History Tour features many famous black Americans in our history.  Is there a particular person or story that stands out the most?

A woman sits outside her home. She has a blue desk in front of her.
Dorothy West. Photography | Judith Sedwick

TD: We begin the African American history tour at the house of Senator Edward W. Brooke, the first Black elected to the Senate since Reconstruction.  The tour includes local heroes in the Black community, but the most prominent, besides the Senator, is the house of author Dorothy West in the Highlands.  As a young woman Miss West was in the Harlem Renaissance; she was the Oak Bluffs columnist for decades and wrote dozens of short stories.  Her final tome, The Wedding, edited by Jacqueline Kennedy, stands as a testament of her enduring legacy.

BST: Your Vineyard Haven Walking Tour is self-guided, and is also a new offering this summer.  Of all the things to do in Vineyard Haven, is there one spot, off the beaten path or not, that visitors should take in?

A large, stately mansion sits.  Lush green grass in front of it, blue sky.
The Martha's Vineyard Museum. Photography | MV Vacation

TD: I suggest a walk down Lagoon Pond Road.  It’s just off the beaten path of Five Corners, and leads down to the Lagoon, for an inland water view.  At the same time, look to the hill on your right.  The Martha’s Vineyard Museum is a majestic building housing myriad Vineyard archives.  Two sights at once capture the charm of nature and the mystery of history in one vista.

Unique things to do in Martha’s Vineyard

Before you head out to the Vineyard for sun and recreation, check out Dresser’s many books on its history, here. And then check out his seven self-guided tours…that extensively cover the whole island. His World War II history tour leads people out through Chilmark, and into Aquinnah. His Railroad history tour, down to South Beach. Preview all of Dresser’s self-guided tours here. Happy exploring!☀️

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