Dennis Jason

I must go down to the seas again, to the lonely sea and the sky, And all I ask is a tall ship and a star to steer her by.

Obituary

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 Cemetery, Chilmark
Saturday, October 4th @ 1030am
Reception to follow @ Chilmark Community Church, Fellowship Hall
Questions: Samantha.Jason@gmail.com

My comfort will come from the sea.
The stillness of calm waves will gently drift by
I will be as one with the sea.

When the sun sets on the ocean blue, remember me
as I will always remember you.

As the sun rises…go live life as full as can be
Apart…you and me…but be at peace for I am free.
~Capt. Chad Theesfeld

Gallery

Memory wall

October 6, 2025

I was stationed at CG Sta Menemsha from 20 Nov 78 until 10 Aug 82. I became friends with your grandfather Louie and your dad Denny. I spent many hours on the Little Lady helping Denny & shooting the breeze, I had the honor one day to get uw & fish for scrod with Denny. One day I said to Capt Donald Pool, Cap she’s a foggy one today and he replied “ she ain’t foggy until you can cut her and stack her on deck” that reply stuck with me. On 11 July 1980 you could cut & stack it on deck. The stationed rcvd a call for help from the RV Albatross, she was south of Nomans with a crewman onboard with a collapsed lung and needed immediate Medivac. I was the duty coxn that day. As we passed the Little Lady Denny yelled out hey Tone where you going? I told him and he said “ you need a radar operator” I replied let’s go. Denny stuck his head in the radar & called off course changes, we cut buoy #29 that day and ran at a rather fast pace. We rendezvoused with the RV transferred the crewman by stokes litter and raced back to Menemsha with Dennis calling out course changes. When we arrived at the dock Chief Andersen was waiting for us and he didn’t look happy, you see we failed to travel at a safe speed in the pea soup fog. I told the Chief I had Denny on the radar and the Chief let me slide. I found out later that we saved that crewman’s life because we got him to the awaiting ambulance so quickly, I never could have done it without Dennys help. When I got ready to transfer Denny gave me his bosn pipe and I wore & used it for my 21 years. After I retired I mailed it back to him and asked if he’d pass it along to another young coastie. 2 years ago we had a reunion of friends at Menemsha, myself, Joe uva, Chuck Fiore & Albie Clements. We stopped by to visit Denny and see how he was doing. He was hanging in there. He gave me that Bosun Pipe back and said I want you to have it you earned it. I’ll never forget my time I spent with your Dad and how he friended a young kid from Worcester. Fair Winds & Following Seas Shipmate.

Anthony W. Fiore Jr.

September 14, 2025

My sincere condolences, Sam, Dave, Vivi & Owen!

With much love,
Rene

Rene Sancinito

September 13, 2025

Dennis was the first friend that I ever had on island...We met when my dad brought me along with his sea explorer troop to menemsha ..we swam together off the Coast Guard dock ..I was probably 8 years old...Salt of the Earth !

Rick O'Gorman

September 12, 2025

We send our condolences, to you, the entire Jason family, on the sadness of losing Dennis. We shared many a conversation with him across the shared stone wall between our properties and Bob always enjoyed talking and visiting with him when he was the Harbormaster. Thinking of you....
Connie and Bob Taylor

Connie and Bob Taylor

September 12, 2025

Sorry for your loss and prayers to all the family!

Chester L Cook

September 11, 2025

My condolences to Dennis' family. He was my classmate at the high school, class of '66.

Bill Wilcox

September 11, 2025

Denis was an incredible man. I cant thank him enough for the happiness that he brought to my family.....countless times, he unloaded my kids from the boat, and made sure they had safe, and happy weekends in Menemsha. Dennis was the complete man, who had everything, except more time with us. I am saddened that I didnt, and wont get to see him again.

John Patete

September 11, 2025

Dennis and I fished for oysters on Chilmark pond one winter. It froze over and he asked me to come with him one day. We cut holes 🕳️ with chainsaws and dragged bull rakes along the bottom. We got good weights and made our payments.. years later we laughed about it! “ Remember that time! “ rest in peace Capt!

Jon R. Mayhew

Service

Donate