Robert Milton Congdon, died peacefully in his home overlooking the sea, harbor and boats of Fort Lauderdale, Fla. on May 15, attended by his loving wife Dianne.

Known as Bob, or Captain Bob, he was a longtime former Chilmark resident. Born in 1936 in Rockland, Me., to Stafford and Virginia Leach Congdon, Bob formed his love of the sea in his early years from his bedroom window overlooking the West Penobscot Bay in a house known as Roxmont, which later became the home of DownEast magazine.

His grandfather and namesake, Robert Milton Leach, a descendant of the early colonial American Hubbard family, taught him the fundamentals of boating on Webster Lake in Franklin, N.H. He later sailed as crew during his high school years in Hingham.

After graduating university and a stint in the Navy, Bob married Patricia Wilson Congdon. They raised two sons, Bill and John, in St. Louis, Mo. He spent 31 years at A.W. Chesterton as a salesman, trainer and mentor to many who still today credit him with helping them to jump start their careers.

Bob fell in love with Martha’s Vineyard and in 1965 built a home in Chilmark overlooking Menemsha harbor and the sunsets of Vineyard Sound. In 1978, he married his second wife Dianne Jurenka Congdon, and along with stepdaughter Abby Thompson, established a home in St. Louis while continuing to summer on the Vineyard.

In 43 years of Vineyard life, there were countless friendships formed, boats acquired, cleaned and docked, fish caught, lobsters pulled, rafts anchored in Menemsha Pond, days on Lucy Vincent, sunsets watched in search of the green flash, and nights spent at the potlucks of Squid Row.

Upon retiring, Captain Bob and first mate Dianne spent 10 years living aboard the vessel Escapade, traveling up and down the Eastern seaboard on the Intracoastal Waterway from Key West to Maine. In later years, they established a home in Fort Lauderdale on the New River, where they spent many hours exploring river life.

Bob was a humble, generous person, with a passion for the outdoors, marine life, good food and spending time with family and friends. He will live on in the hearts of many.

In addition to his wife, he is survived by his sons Bill, John and his wife Sheila; daughter Abby and her husband Eric; brother Malcolm and his wife Mary; and sisters Cyncy and her husband Mike, and Diana and Bevy.

A private celebration of life will be held later this year in Rockland, Me.

For online tributes and donation information, visit the funeral home of