At the second of two northern tips of the mostly triangular island of Martha’s Vineyard perches the town of Oak Bluffs. It is one of the smallest communities in the Commonwealth of Massachusetts, but it packs a powerful personality. The name alone conjures up images of summer days and ice cream and windswept, tree-bordered beaches. Much of Martha’s Vineyard as a whole caters to the transient seasonal community, and Oak Bluffs is no different... but then again, maybe it is.
An Overview of The Vineyard
Martha's Vineyard has been a destination for adventurous voyagers for 10,000 years, when it was still seventy-five miles from the beach. Summer hunters first visited then, but didn’t stay because of the inhospitable weather. Two thousand years later, after the deer, elk and smaller mammals replaced the mastodons and mammoths, they moved here permanently. A few thousand years after that, they became the original Islanders when the ice age glaciers began to melt, the ocean level rose and the low-lying land that connected it to the mainland was flooded. Native Americans welcomed the first white visitors in the early 1600s, 20 years before the Mayflower arrived in Plymouth. The Vineyard has for 150 years been a resort community, first attracting Methodists to summer religious revival meetings under the oaks of Edgartown (now Oak Bluffs.) Today, it is the home of about 15,000 year round residents, a number that swells to roughly 100,000 in summer, when those who either own or rent real estate return to enjoy the Vineyard's beaches, six towns, beautiful water and inland vistas, and to find entertainment that is quintessentially "island," according to an historic overview provided by Edgartown-based Sandpiper Realty.
Diversity of People
Dennis DaRosa, vice president and co-owner of DaRosa’s, a printing and retail shop on Circuit Avenue in Oak Bluffs, considers himself “an island person.” He says each small community on the island has something to offer and it all “enriches my life.” All the same, he grew up in Oak Bluffs, and along with his day job, he also serves as the volunteer president of the Oak Bluffs Association. The Martha’s Vineyard Chamber of Commerce describes the association as “a voluntary membership group of over 140 businesses and community members established in 1991. They are dedicated to promoting the natural beauty and historical charm of the Oak Bluffs area, while fostering economic health though a strong and vibrant business community.” The enthusiastic DaRosaclearly takes his role seriously. After almost an hour on the phone with him, it would be impossible not to want to visit the town at the next available opportunity.
“We say we’re the most diversified town on the island,” says DaRosa, “and not just ethnically.” He does, however, point out that ethnic diversity is a part of Oak Bluffs’ distinctiveness. He says that even before any Civil Rights Act, Oak Bluffs was ethnically diverse, and that even as long ago as the Civil War, African American freedmen would come to the island to vacation. They found, according to DaRosa, that the residents of Oak Bluffs are a friendly and open-minded people, and the black and white communities have grown together and influenced each other for the good. A significant Portuguese population also moved into the community, impacting the town particularly through an annual Portuguese Feast in July. An international crowd has been converging on Oak Bluffs since the early 1800s.
Getting to Oak Bluffs, as to any island community no matter the time period, requires a bit of a twist on the traditional road trip, but it is still relatively simple. Nowadays people with private planes or boats have the advantage of the private Trade Winds Airport or the Oak Bluffs Marina, respectively. But there are also a number of ferry options available, leaving from Hyannis, Falmouth, and Nantucket, Massachusetts, and QuonsetPoint, Rhode Island. Within the island there is public transportation, including within Oak Bluffs itself, in spite of its reputation as a self-sufficiently pedestrian-friendly location.