Historic Tales of Oak Bluffs, by Skip Finley, The History Press 2019, 176 pages, softcover, $21.99

From 2012 to 2017, Skip Finley wrote more than 250 columns for the Vineyard Gazette, centering on the history and unique character of Oak Bluffs. Those columns made for consistently fascinating reading, sketching in aphoristic detail the lives and historical legacies that have combined to make the nature of this place all Vineyard people love; many readers clipped these short chronicles and saved them. Now those readers and a broader audience get to hold a book in their hands. The History Press has collected a generous selection of those columns as part of its American Chronicles. These are columns that richly deserve a longer life.

The arrangement moves from the personal to the panoramic with smooth, eloquent confidence. The author starts with his own story, with his parents and his friends’ parents being some of the 20th century African Americans who found a welcome in Oak Bluffs that they could find at virtually no other seaside community in the country — and certainly scarcely anywhere else in New England. The kids of that earlier time were granted a degree of autonomy that’s all but vanished in the 21st century, allowed to walk unaccompanied into town at night. “Freedom to roam Circuit avenue at night,” Finley writes, “taught us how to interact with adults, handle money and develop self-respect without fear.”

From such personal focus the scope broadens to the Island’s deep history in the Pleistocene, when Martha’s Vineyard slowly separated from the mainland and retreating glaciers left behind a wide variety of kettle ponds. For centuries, the area now known as Oak Bluffs was occupied in a rough ecological balance by the Nunnepog tribe of the Wampanoag Nation that covered the whole Island at the time. It was the Nunnepog who bore the brunt of the first European settlers. For years, as the whaling industry boomed, the Vineyard, along with Nantucket, New Bedford, and other key towns, became, as Finley puts it, “an integral part of what was the time’s Middle East — but for a different type of oil.”

In short order, in 1641, Thomas Mayhew purchased the Vineyard, and Ogkeshkuppe, then Great Harbor Township, became Edgartown — from which would in 1880 be calved Oak Bluffs, which was originally known as Cottage City and sported some of the tiny, gorgeous wooden cottages for which Oak Bluffs is famous even today.

The author tells the stories of those little cottages and the other architectural features of the area — and all the fascinating people connected with them. People like house designer Samuel Freeman Pratt (1824-1920) or ambitious land developer Tarleton Cadwallader Luce, who was born in Edgartown in 1822 and eventually decamped to California when his extensive speculations went awry. There were high-profile celebrity guests — President Grant visited in 1874, for instance, and Dorothy West first came to Oak Bluffs in 1908.

All these stories are told in brief but insightful detail, and the wonder of Finley’s account is that the scenarios glow with human interest in all cases; the author is a scrupulous chronicler, but he’s also a fine dramatist of personalities. “We honor their memory by knowing their story,” is the simple philosophy on display.

“We’re Wampanoag, European immigrants, born free and descended from slaves of color, Portuguese, Azorean, Cape Verdean and Brazilian year-round and who knows how many other nationalities and colors during the tourist season,” he writes when reflecting on the vigorously diverse nature that has always characterized Oak Bluffs. Today the town houses a high school, two movie theatres, a ferry terminal, a lighthouse, an elementary school, a library, a golf course, a famous carousel, a state park, a private airport . . . and of course a hospital. “Thanks to our being the home of the hospital,” the author points out, “almost everyone not born at home or in an ambulance is born in Oak Bluffs.”

There are 429 homes in the Cottage City Historic District, 452 pretty streets, 55 named parks, 17 ponds and seven beautiful beaches.

Thousands of visitors every year see all of that and delight in it, but hardly any of them know the long and intensely interesting history behind it. Thanks to Historic Tales of Oak Bluffs, that history is now brought to life in the stories of all the people who made Oak Bluffs what it is. And those longtime Skip Finley fans can finally dispense with their yellowed clippings — they’ve got a neat and well-illustrated book at last.