Dennis daRosa

– Jeremy Driesen

Oak Bluffs has no mayor, but friends always joked that if there was ever an election, Dennis daRosa would have won by a landslide. The longtime vice president and co-owner of daRosa’s Martha’s Vineyard Printing Co. was a fixture at the upper end of Circuit Avenue his whole life, since he first began learning the printing trade from his father, Antonio, until last week, when Dennis passed away at the age of 71, following a yearlong battle with cancer.

Born and raised in Oak Bluffs, Dennis excelled at baseball, football, academics, and printing. The former were his loves. The latter became a passion he learned at the side of his father, his mother Cecilia, his older brother Tony, and his sister Cindy. In the back of 46 Circuit Ave. he learned to set type, fix machinery, and run a potential finger-crushing machine called “the Kluge.” Purchased by his dad in 1950, a year after Dennis’ birth, it was the first printing machine on the Island with an automatic paper feeder. It sped up the printing process markedly, but if you didn’t hit the hand brake at the right moment, it might flatten your fingers. Perhaps that’s how Dennis became a flame-throwing Little League pitcher and a sleight-of-hand high school quarterback.

When it came time to choose a college, the printer’s son naturally accepted the best printed offer. His UMass acceptance in engineering came as a computer-generated letter. Babson College’s acceptance came on an engraved card. He chose Babson.

His interest in business and possibly a career in economics changed radically in 1969, when early in his junior year in college, his father unexpectedly passed away. The family business was in safe hands with his brother and mother in charge, so he returned to Babson, but with an eye toward returning to the Island after graduation.

His plan was to marry his high school sweetheart, Candy Cullen, whom he’d met in his junior year at Martha’s Vineyard High School, and help his family’s business grow. He succeeded famously at both, marrying in 1971 and formulating a plan to expand the business to include supplying copiers, computers, payroll systems, and printing services Island-wide.

The business grew to the point where his brother served as company president and ran the printing operation, while Dennis headed up the office supply and sales division. His family expanded just as rapidly, with the birth of his daughter Stephanie in 1975, and son Philip in 1978. Both ultimately chose to make the Vineyard their home as well.

As the years passed, Dennis became the pied piper of office supplies, spending much of his time selling, servicing, and delivering equipment, supplies, and good cheer around the Island. It was a job he enjoyed because he loved people. His jocular manner could win over even the most harried local businessperson, and his endless well of patience allowed him to smile at even the most irksomely demanding customer.

His sense of civic duty and loyalty to Oak Bluffs were well known. Along with Renee Balter, he helped to grow the nonprofit Oak Bluffs Business Association into a unique and effective organization. Under their leadership, in 1991 the OBA launched Harbor Fest, and created the information booth at the bottom of Circuit Avenue. The OBA also took over and grew the end-of-season Tivoli Day celebration, which had originally been created by Bill and Margaret Stafursky as a sanctioned bike race in the late ’70s. Dennis was president of the OBA for decades, and got so much joy and excitement out of organizing the booths and working with all the shopkeepers, restaurateurs, vendors, and musicians to make Tivoli Day the huge success it became.

Dennis served on the board of the Vineyard’s Chamber of Commerce, the board of the Vineyard Open Land Foundation, and recently joined with like-minded friends and colleagues who share concerns for the Island’s future to form Vineyard FutureWorks.
As much as he was a lover of travel, boating, football, music, reading, and learning, what he loved most was his time with family and friends, the ability to address the needs of his customers, and the chance to make a difference in his community. He cherished his home in Chilmark, created with his wife Candy, and absolutely loved hosting parties, never failing to warmly welcome anyone and everyone who found their way to his door. No one loved a party more than Dennis. Those who called him “friend,” which was nearly everyone he met, long ago concluded that well before longtime Patriots’ tight end Rob Gronkowski said of himself, “Yo soy fiesta,’’ Dennis owned the label.

Dennis was a devoted family man, businessman, and Island man. He is survived by his wife of 49 years, Candace Cullen daRosa, his son Philip E. daRosa and partner Ann Quigley, his daughter Stephanie R. daRosa and partner James Bohan, his granddaughter Iyla Grace Bohan, his brother Tony daRosa and wife Melanie, his sister Lucinda daRosa Barrett, his sister-in-law R. Blue Cullen and partner Kurt Freund, and six beloved nieces and their husbands and partners.

Services will be private, but one humdinger of a party will be held to celebrate his life when the pandemic allows.

In lieu of flowers, it was Dennis’s wish that contributions be made to the Island nonprofit he helped create, Vineyard FutureWorks: Vineyard FutureWorks, P.O. Box 1554, Vineyard Haven, MA 02568.


  1. We met Dennis years ago when our two offspring spent a few years on the vineyard working in food service. He was indeed a true ambassador, a thoughtful host and a cheerful man. I remember well the times we spent with him, Candy and Stephanie during our trips to MV. Rest well and God speed, Dennis.
    Gene Forsythe
    Canby, OR

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