See: http://trees.ancestry.com/tree/7446586/person/-1091754476

Word has it that Caleb left home (Nova Scotia) at the age of 13 and became a crew member on a ship. He then continued to sail around the world 10-12 times, including voyages that rounded Cape Horn. Once giving up the sea life he built a coal, wood and ice business in Chelsea MA, that burned to the ground once, was rebuilt and then lost a lot on a relative who was keeping the books for him.

additional Info on Caleb
alinrenoadded this on 29 Apr 2010
The 1892 and 1893 City Directories show that Caleb was in business with his older brother, William Stuart. They had a Wood & Coal business, DALRYMPLE BROS., at 100 Winnisimmet and he was living with his parents at 149 Spruce. Both addresses are in Chelsea, Suffolk County, MA The 1871 and 1881(Census) shows that Caleb was living with his parents in Maitland, Hants County, Nova Scotia. It is possible that he did leave home and became a crew member, but I have found no records etc to show this.

1910 United States Federal Census
Name: Caleb C Dalrymple
Age in 1910: 46
Birth Year: 1864
Birthplace: Canada [Canada English]
Home in 1910: Somerville Ward 2, Middlesex, MA
Race: White
Gender: Male
Immigration Year: 1890 [1880]
Relation to Head of House: Head
Marital Status: Married
Spouse's Name: Mary A Dalrymple
Father's Birthplace: Canada [Canada English]
Mother's Birthplace: Canada [Canada English]
Household Members: Name - Age
Caleb C Dalrymple: 46
Mary A Dalrymple: 35
John Dalrymple: 17
Linnie Dalrymple: 12
Charles A Dalrymple: 10
Mary C Dalrymple: 7
Alex D Dalrymple: 4
Franklin Dalrymple: 3

1920 United States Federal Census
Name: Kellem C Dalrimple [Caleb Dalrymple] [Hellen C Dabrimple] [Kellem C Dalrimple]
Age: 53
Birth Year: abt 1867
Birthplace: Canada
Home in 1920: Cambridge Ward 11, Middlesex, MA
Race: White
Gender: Male
Immigration Year: 1890
Relation to Head of House: Head
Marital Status: Married
Spouse's Name: Mary A Dalrimple
Father's Birthplace: Canada
Mother's Birthplace: Canada
Home Owned: Rent
Able to Read: Yes
Able to Write: Yes
Household Members: Name - Age
Kellem C Dalrimple: 53
Mary A Dalrimple: 43
John E Dalrimple: 26 [20]
Lena Dalrimple: 22
Charles A Dalrimple: 19
Mary C Dalrimple: 17
Alexander Dalrimple: 14
Franklin Dalrimple: 12 [62]
Robert Dalrimple: 9
Sumner Dalrimple: 7

1930 United States Federal Census about Cleb Dalrymple
Name: Cleb Dalrymple
Gender: Male
Birth Year: abt 1865
Birthplace: Canada
Race: White
Home in 1930: Cambridge, Middlesex, MA
Marital Status: Married
Immigration Year: 1890
Relation to Head of House: Head
Spouse's Name: Mary Dalrymple
Father's Birthplace: Canada
Mother's Birthplace: Canada
Occupation:
Military Service:
Age at first marriage:
Household Members: Name - Age
Cleb Dalrymple: 65
Mary Dalrymple: 55
John E Dalrymple: 37
Charles Dalrymple: 33
Mary Dalrymple: 26
Alex Dalrymple: 24
Frank Dalrymple: 22
Robert Dalrymple: 19
Summer Dalrymple: 17