Father. Son. Brother. Grandfather. Friend. Cousin. Uncle. Fisherman. Coast Guardsman. Harbormaster. Boat Builder. Home Builder. Collector. 

Dennis was born on February 24, 1949, and passed away peacefully at his home on September 10, 2025, after a long health struggle. He was a lifelong Islander—a fisherman, brother, uncle, friend, Coast Guard serviceman, boat builder, harbormaster, model-maker—and above all, a devoted father and grandfather.

He grew up in Dartmouth, MA, the son of Leonard and Hilda Jason. His father had fished out of Menemsha for many years before relocating the family permanently to a quiet piece of land on Chilmark’s North Road, where they built their own homestead. That home remained Dennis’s anchor until his final days.

A graduate of Martha’s Vineyard Regional High School, Class of 1966, Dennis went on to serve his country in the United States Coast Guard—a path shared by many Islanders who felt both the pull of the sea and the call to protect it. Working alongside his brother, he helped build many homes on the Island, but at heart, he was always a fisherman. He was best known for his beloved fishing vessel, the Little Lady. After decades at sea, he passed the Little Lady on to his son, Denny, and later served as the Menemsha Harbormaster for ten years before retiring a few years ago.

Family was the center of Dennis’s life. He leaves behind his cherished grandchildren, Vivienne, Owen, and Quint. Though their time together was too short, they will grow up knowing their grandfather’s quiet strength, his words of wisdom, and his boundless love. He is also survived by his son, Denny—his pride and joy—who inherited his father’s steadfast character and deep love for fishing and this Island community; his daughter, Samantha, who he never missed a chance to tell how proud he was of her; his daughter-in-law, Jesse; and his son-in-law, David.

Dennis is also survived by his brother and best friend, Leonard Jason Jr.—his lifelong protector and fiercest advocate—who can now, at long last, rest from watching over him. He leaves behind his nieces, Andria and Alexia Jason; and his stepson, Bruce Gray, who lovingly stepped in as caregiver and advocate during Dennis’s final months, for which his family will be forever grateful.

Dennis’s first love was always the Little Lady. The family, together with the Vineyard Fishermen’s Preservation Trust and the Martha’s Vineyard Museum, is currently working to restore her so she may return to her Island port as a floating museum. In lieu of flowers, gifts in Dennis’s memory may be made to support the Little Lady’s rebuilding. His love and concern for her never wavered—she remained in his thoughts every day until the end. 

Graveside Service @ Abels Hill Cemetary, Chilmark
Early October. Information to follow.

Online Tribute: https://www.online-tribute.com/DennisJason