Billie Jean Sullivan’s connection to Martha’s Vineyard began in a way that feels almost predestined. At age 19, while still a student at an arts school in New Haven, Conn., she visited the Island and instantly felt a deep connection to Oak Bluffs. She started her journey as a chambermaid at the Ship’s Inn (now the Madison Inn) on Kennebec avenue. But it wasn’t until 2010, equipped with an administrative arts certificate and experience working in arts administration in Fairfield, Conn., that she decided to make Oak Bluffs home. Today, she is the executive director of the Oak Bluffs Association (OBA), a nonprofit organization dedicated to promoting the town’s businesses, activities and attractions. Her cheerful dedication is the signature of her leadership style.

Q. How do you describe Oak Bluffs to someone who’s never been here before?

A. It’s more funky and bohemian, with a diverse history unlike any other town on the Island. And live music year-round is definitely a thing for O.B.

Q. When did you decide to get involved and make an administrative commitment to the town?

A. I’ve owned four businesses, including Tivoli Paint in Vineyard Haven, and I had experience in town planning in Connecticut. So I can work with people and numbers. When I was working at Craftworks on Circuit avenue, artist Renee Balter, who started the OBA with Dennis daRosa, told me to apply for the position of executive director, and I succeeded Christine Todd in 2022.

Q. What is your role in the politics of Oak Bluffs and in select board decisions?

A. If I see something coming up for a business – like the restaurant Pawnee House asking to add outdoor tables – I go right to the business, we talk about it and I try to back them at town meeting. Business is what makes this town thrive, and I hope we carry some clout when the decisions are made.

Promoting shoulder-season events is a goal for Billie Jean. Ray Ewing

Q. As a resident of Oak Bluffs, I’ve seen and appreciated the many improvements, from the refurbishment of Circuit avenue to the new North Bluff roundabout this season. What’s the next project to get much-needed attention?

A. The Oak Bluffs information booth, for which residents at town meeting voted to approve a one-time $15,000 renovation fee. Up to 50,000 people go to that booth in the summer where our longtime Oak Bluffs “ambassador” Leo Gagnon keeps track with a clicker. And now with the spruced up welcome kiosk and the rebuilt variety store next to the colorful Flying Horses, that little triangle is our historic front door to Oak Bluffs.

Q. Right behind that front door is the back door – the Island Theatre. Can you share any progress with that blighted property?

A. We all carry heavy hearts when we look at the building. Something has to be done. As far as I know there are some interested parties, but the obstacle to advancing any plans there, or at some other properties in town, is the issue of wastewater.

Q. At the kiosk, Leo will provide visitors with the new Historic Walking Tours of Oak Bluffs brochure, which you’ve just launched this season. This free map is a keeper!

A. It’s the first redesign and update in 20 years, thanks to OBA member and graphic designer Linda Bryant and local historian Tom Dresser. It’s a color-coded map of individual historic walking tours laid out so you can walk each of the four different Oak Bluffs districts – The Highlands, The Gold Coast, The Camp Ground and The Copeland – either one at a time or consecutively.

Q. I know you love “all your children equally,” but did you discover a nugget about Oak Bluffs that you didn’t know before this project?

A. Of course people often come to Oak Bluffs to tour the gingerbread cottages in the Camp Ground – but there’s so much more here. People don’t know too much about the Copeland District, more of a Victorian residential area behind Union Chapel designed by landscape architect Robert Morris Copeland, or the Highlands, over past Our Market and above the old Ocean View. I think it was Oak Bluffs author Skip Finley who named Seaview avenue with the big, glorious houses the Gold Coast.

We also highlighted the African American Heritage Trail sites which are so important to the history and culture of Oak Bluffs. There’s just so much historical information in the map, and with the way it all comes together, I think people will hold onto it, because it highlights a trip, a tour and a memory all in one.

The third annual LGBTQIA+ Pride Weekend happens June 7 - 9. Ray Ewing

Q. How do you finance these tourism projects like the map and your many events – especially in June with Pride Weekend, HarborFest, and Juneteenth?

A. A few grants come through to help us with our events, and Pride Weekend gets support from all over the Island since it has an Island-wide reach, not just Oak Bluffs.

Q. Who brought the original 
energy to the Pride effort?

A. This is our third annual event, and it was Sofie Green, vice president of the OBA board and owner of Island Outfitters, who really saw a need that was not being addressed in our community and Island-wide. Now the event is always the second Saturday in June, and it has grown from a funky little parade down Circuit avenue to being supported by the Martha’s Vineyard Hospital and so many individuals, and it’s recognized by the state with funding through the Massachusetts Cultural Council. It’s good for business, it’s good for the town and most of all it’s good for the people of the LGBTQIA+ community. It’s just a really joyful, free, fun day.

Q. You barely get a breath, and the next Saturday, June 15, is the 32nd annual HarborFest!

A. Very busy, yes, but all of our OBA events are driven by the shoulder season. There’s enough going on in July and August. We want to see more commerce in the shoulder season. HarborFest this year will have 60 vendors and music. Tivoli Day in September is also shaping up to be great!

Q. How do you approach the week in August when Illumination Night, the fireworks and the Fair stack up?

A. Our Oak Bluffs businesses are working at full capacity. They’re trying to stay open as long as they can to serve the tourists that pour through here in August. I wish those events could be spread out. That’s something to think about! Imagine the fireworks in July. July could use a little boost. That third week in August, everyone is overburdened – especially in Oak Bluffs. I wish the town would think about it.

Q. What’s your favorite Island experience in the summer season to take you away from all these responsibilities?

A. I try to make Vineyard Haven’s First Fridays, and I make a point of exploring Edgartown’s restaurants and shops. I like to go to Menemsha for seafood and walk about, and I love Lambert’s Cove Beach and the other hidden beaches throughout the Island. The natural beauty here still amazes this washashore.


Sissy Biggers is a frequent contributor to Martha’s Vineyard Magazine and a regular contributor to the Vine.