Aquinnah • Chilmark • Edgartown • Oak Bluffs • Tisbury (Vineyard Haven) • West Tisbury

Photo Ops:

There is perhaps nothing more iconic to Martha’s Vineyard than the famous gingerbread cottages. These whimsical homes were once part of a Methodist campground and now add color and flair to the streets of Oak Bluffs. If you’re looking for something more off the beaten path (literally), head to the Aquinnah Cliffs and take a bus or bike tour to explore the sprawling beach and astounding clay cliffs.

Favorite Spots:

The Vineyard Playhouse operates year round, presenting both contemporary and classic plays and always working toward their goal of entertaining and enriching island visitors and locals alike. For a fun place to go after a show, check out Bad Martha Brewery, open in Edgartown for the summer season and Christmas, and try a 508 IPA or one of their other specialty craft beers.

Mom & Pops:

The cutest independent bookstore on the island, Edgartown Books is the place to go for some relaxation time. Head to the quaint reading area or out back to the quiet courtyard garden to enjoy your favorite title. If you need a cup of coffee to go with your book, Behind the Bookstore offers delicious breakfast sandwiches and reviving cups of joe.

Don’t Miss!

Held each March, the Martha’s Vineyard Film Festival screens independent films from around the world. In October, enjoy four days and three nights of local culinary delights at the annual Martha’s Vineyard Food & Wine Festival.

A day in the life of: Bridget Tobin, terminal manager for the Steamship Authority

By Julie Craven Wagner

Passengers on the Steamship Authority ferry to Martha’s Vineyard encounter a variety of emotions as they make their way across Vineyard Sound. For some, it is anticipation of another summer at their favorite place, and for others it’s the relaxed exhalation of returning home. All will find themselves in the capable graces of Terminal Manager Bridget Tobin.

Tobin, who is in her 45th year working for the Steamship Authority, says that she has “seen it all.” Back in January 1974, Tobin took what she thought would be a part-time job working in the vehicle reservation bureau and has never left. Back then reservations were entered and catalogued on index cards, and as a result, Tobin actually knew every person on the island by name. Technology has streamlined the process today, but Tobin says that they still call every reservation personally on the phone when the schedule changes due to weather. “The customers provide an email address when they make a reservation, and we send out a mass communication, but I think it is still important to call each person to make sure they understand the changes, particularly since they made the reservation so far in advance,” Tobin says.

Passengers who have an urgent need to secure passage on a boat for their vehicle are often encouraged to have a conversation with “God,” the insider nickname Tobin has earned within the organization. But Tobin says she prefers the moniker an islander bestowed upon her, the “Tobin Bridge,” and has been referred to as a “Ferry Godmother” by a particularly grateful customer.

Tobin spends her days in Vineyard Haven during the off-season, and during the summer months she runs the Oak Bluffs terminal, a visually stunning port vulnerable to certain wind and weather conditions. She says weather is always a factor in her days and a constant point of evaluation in determining service. “Today it is much easier to predict the weather, but 30 years ago, we pretty much relied on the reports from the captains as they made the crossings.”

Tobin recalls her greatest challenge over the years when a storm hit the Vineyard just as the busy Labor Day weekend started. “I got to work at 3 a.m. on that Saturday and it looked like an evacuation from World War II, cars lined up as far as you could see. We were successful in getting every last car off the island that needed to by 2 a.m. the following morning; it was a miracle really.” Subsequently, both ports on Martha’s Vineyard were closed for two days, reopening Tuesday.

Growing up in Falmouth, Tobin says she used to drive along the coastline and look over at the island and wonder, “What do those people do all year over there?”—never dreaming she would marry an islander and live her life on the Vineyard. Tobin is an active member of many island-based community organizations including the Martha’s Vineyard Chamber of Commerce, where she has been a board member for a number of years and served on the development committee to build a new hospital on the island. In her precious free time, Tobin says that she makes a point to enjoy everything the island has to offer. “Even just driving up-island is special, as I get to experience the unique views,” she says. “And the summer is always fun. For me, the increased cultural offerings of music and films make it difficult to choose what to do.”

Tobin sums up her 45 years at Steamship by saying, “There have been so many rewarding things about working at the Steamship Authority over the years, but it is usually about the people of this island. It has felt very rewarding to help the island people and be part of the changes the island has seen over the years. Unless you are lucky enough to live here, you don’t fully understand the unique nature of this island.”

Julie Craven Wagner is the editor of Cape Cod HOME.