Vineyard visits

Tom Dresser’s latest book takes a look at tourism on the Island.


After writing 12 books about the history of Martha’s Vineyard, Tom Dresser is nothing short of an expert. His latest addition, “The Rise of Tourism on Martha’s Vineyard,” is a testament to Dresser’s niche expertise, as he skillfully maps out the Island’s history, connecting relics of the past to staples of the present. 

For Dresser, this book was in part born from personal experience. For 12 years, he was a tour bus driver, showcasing the Island’s treasures and explaining its history to eager visitors. He developed a keen understanding — not only of the Vineyard, but also of those who would depart from Woods Hole in search of the Island’s serene beauty and anticipated adventures. His personal experience, combined with diligent research, gives Dresser’s voice a unique sense of clarity and nostalgia, a precision met with romanticism for the Island he loves. 

Dresser started working on the book in September 2018, and said the pieces of it came together with ease. When explaining the writing process, Dresser recalled a quote from Bob Dylan about his album “Rough and Rowdy Ways.” “Dylan said some of the lyrics are just up there,” Dresser said, pointing to the sky. “And they come down into his songs. When that happens, it’s so perfect because you don’t have to argue with it — it’s all right there.” The ease with which Dresser wrote this book is reflected in its natural flow, with no fact or facet feeling out of place. 

Dresser organizes his book both chronologically and by focus, allowing readers to see the overlapping factors that changed the physical and cultural landscape of the Island. Dresser begins with an acknowledgement of the Wampanoag tribe, the people of the first light. According to archeological artifacts, including carbon-dated settlements, bones, stone tools, and trade artifacts, the Wampanoag settled on the land that is now Martha’s Vineyard 10,000 years ago, before it was cut off from the mainland and became an island. “Everyone who followed could be labeled a tourist, visitor, wash-ashore, or off-Islander. The only natives are the Native Americans,” Dresser writes. 

From there, Dresser explores the early origins of tourism on Martha’s Vineyard in the 19th century by weaving together the story of two groups — the Methodists of Wesleyan Grove and the land developers of the Oak Bluffs Land & Wharf Co. In these beginning chapters, Dresser’s strength as a historian, as well as a writer, help bring the intertwining stories together.

The Methodist pilgrimage to Wesleyan Grove began in 1835, with nine tents pitched on the Campground. As Dresser writes, the retreat quickly surged in popularity; by 1858, only 23 years later, the event hosted more than 12,000 people. Families who participated in the pilgrimage started returning to the Island days before the retreat in order to savor the Vineyard’s natural beauty, Dresser writes, thus transforming Wesleyan Grove from an exclusively holy haven to a summer resort. Cottages gradually replaced tents, and by the turn of the century, more than 500 of the gingerbread-style cabins we recognize today in Oak Bluffs were constructed. 

At the same time, the Oak Bluffs Land & Wharf Co., led by land developer Erastus Carpenter, was developing the land adjacent to the grove for a summer resort community. Despite Methodist apprehension — and even the construction of a wall dividing the two communities — they melded together, blending their religious services and secular relaxation to create Cottage City, the heart of Martha’s Vineyard early tourism industry.

Throughout the book, Dresser often fascinates us with details that connect the Vineyard’s historical past with the Island we know and love today. One anecdote in Chapter 3 was especially attention-catching. As Dresser writes, Azorean crew members on New England Whaling ships occasionally disembarked from their lengthy voyages to make a new home for themselves on Martha’s Vineyard. One Azorean immigrant fisherman would walk the streets of Oak Bluffs, calling out “alleybut” to let others know he was selling fresh-cut halibut. “Alleybut” was then shortened to “Alley,” a surname proudly carried on by the late John Alley of West Tisbury and Kerry Alley of Oak Bluffs. When John Alley’s father assumed ownership of a general store in West Tisbury, he renamed it Alley’s General Store, the same store on State Road that has been treasured by both locals and tourists for decades.

In Chapter 6, Dresser describes the many joys tourists were able to enjoy at the turn of the 19th century. He recalls the era with nostalgia, writing of hazy summer days spent on beaches lined with bathhouses, or trips to the ice cream parlors or candy shops. Dresser writes that young couples would often go “bluffing” — the act of strolling along the lengthy plank boardwalks that stretched from the Highland Wharf to the shore of the Inkwell, hand in hand, as band music played from the shores. Croquet, bicycle riding, whaleboat racing, the Flying Horses Carousel, horse racing, roller skating — all became staples of the “amusement park atmosphere” that dominated Oak Bluffs. The town even constructed an early iteration of a roller coaster — an 850-foot-long toboggan slide.

The final chapters of Dresser’s book map out the revival of the tourism industry on Martha’s Vineyard after the World Wars. From his many years as a bus tour guide, Dresser understood what attractions drew so many new visitors to the Island. Surprisingly, the most popular attractions on the Vineyard were two bridges. “The first thing they wanted to see was the bridge in Chappaquiddick. Kennedy drove off that bridge,” Dresser said. “And, you know, they want to hear about ‘Jaws,’ and see the ‘Jaws’ bridge, and ask if I was in ‘Jaws.’” Recurring visits from two sitting presidents, Bill Clinton and Barack Obama, also garnered national attention for the Island, and drastically increased the tourism landscape.

Despite his extensive knowledge of Martha’s Vineyard, Dresser’s book does end on a note of uncertainty. COVID-19 has drastically injured the travel and tourism industries, with apprehension from both travelers and local populations. Understanding the pandemic’s full impact on the Island community will require the power of retrospect, and as Dresser writes, “the new normal may be very different from years past.” 

“The Rise of Tourism on Martha’s Vineyard,” by Thomas Dresser. The History Press, Charleston, S.C. Available at local bookstores and retail outlets, including Bunch of Grapes, Edgartown Books, and Phillips Hardware, or online at Please check out the same link for information on upcoming virtual book talks with the author.