Leland Hamilton Jr., 57

Leland at 5 months 

Leon and Leland

Leland and Leon

Leland and Karen

 CHEBEAGUE ISLAND - Captain Leland Hamilton Jr., 57, a life-long resident of Chebeague Island, passed away in his sleep Sunday, May 15, 2005 in Sandwich, Massachusetts of a heart attack.

Leland was born in Portland, February 5, 1948, a twin son of Leland M. and Elsie M. Ross Hamilton. He grew up on Chebeague Island surrounded by his five siblings and a large extended family that encompassed much of the island. Leland was proud of his island roots dating back before the American Revolution.

Leland grew up at the end of an era, the last generation of Chebeaguers to experience relatively isolated island living. He went to the Chebeague School through Junior High, and shared his last name with both of his teachers. He graduated from Greely High School in Cumberland. He was an active participant in boy scouts and church activities and formed a life-long bond with his multi-graded classmates. He was known as the architect of many an intricate brush hut, snow fort, and ski jump. Leland played inter-island ball on the Chebeague team and also played baseball at Greely. After practice, he and Leon frequently hitchhiked from Greely to Cousins Island and rowed home in a punt, because there was no regular boat service from Cousins Island.

He was a preschooler when he started going lobstering with his father on the Marjorie E., the family's lobster boat. As he grew older his responsibilities increased, for that was the way fathers taught their sons. Leland was always a worker and he, and his twin brother, Leon, carved and painted lobster buoy curtain pulls and sold them all over the island while still in elementary school. While attending Greely High School in Cumberland, he dug clams and sold them to the teachers to earn spending money.

Leland joined the Navy shortly after graduating Greely High School. He later became a member of the Portland Fire Department. Eventually, the sea called him back, and he joined the Coast Guard and retired after 20 years with the rank of Senior Chief Petty Officer. After retiring he returned to his roots and was a lobsterman until his death. He enjoyed taking family and friends to the lobster boat races in his boat, My Girls. Leland was a licensed sea captain.

Always willing to lend a neighbor a hand, Leland served as a director of the Chebeague Island Community Center and was a volunteer at the Chebeague Island School where he recently talked to the children about lobstering. He was a long-time member of the Masons.

Leland was an avid outdoorsman. He loved being in the woods, far removed from civilization. His passion was hunting. As a boy he and his brother hunted for ducks along the shores of Chebeague using tollers hand carved by their grandfather, nationally known decoy maker, Willie Ross. They shot rabbits in the woods of Chebeague and traversed many of the Casco Bay islands looking for deer. His passion never waned and as an adult he shared his love of the hunt with his brothers Sherman and Leon, brother-in-law, Shant and many friends. He bonded with this band of brothers, and they hunted throughout the United States and Canada.

He was a wonderful father, loving husband, devoted son and loyal brother. He and his twin brother shared a special bond and were truly kindred spirits. Since early childhood that bond has amazed and inspired everyone who knew them. He will be sadly missed by his family, close friends and the entire Chebeague community

Leland leaves behind his wife, Karen; children; Anna, and Trisha, Lindsey and Loretta, Jamie and Danielle, and Danny and Rebecca; grandchildren: Jenna, Ramy, David, Nathaniel, Shawn and Julian; his mother, Elsie Hamilton of Portland; two brothers, Leon of Chebeague and Sherman of North Yarmouth; and three sisters Loretta Parker of Portland, Lois Cafmeyer of Nokomis, Florida, and Holly Jordan of Old Orchard and many nieces, nephews, and cousins.


In lieu of flowers, contributions may be made to:

Chebeague Island Methodist Church
PO Box 1
Chebeague Island, Maine 04017

Service will be 1 pm, Friday, May 20th at the Chebeague Island

This photo taken with Anna and Tricia was sent to Leland's wife Karen while she was serving Kuwait

Leland with Loretta and Lindsey

Leon and Leland

Sherman, Leland and Leon

Leland with his mother Elsie

Leon and Leland with father Leland


Leland with Lindsey, Anna and Loretta
Leland and Lindsey

Lois, Leland, Holly, Elsie, Sherman, Loretta, and Leon

Chebeague Island School c.1961 - Leland is back row 3rd from left beside his twin brother Leon.
Back row: Michael Hamilton, Leon Hamilton, Leland Hamilton, Med Bowen, Cappy Dyer and Charlie Kuntz
Front row: Polly Smith, Holly Hamilton, Donna Damon and Sharon Burgess

Top row: David Burgess, Steven Slowik, Med Bowen, and Steven Ross
1st Row: Leland Hamilton, Leon Hamilton, and Raymond Ross