Hello Heidi, I have some info that may help you in your search. This is what currently have:
Came from Londonderry, Ireland to Londonderry, New Hampshire November 1725 where he bought a farm of 30 acres from James Rogers.
This is the original Calderwood immigrant who came from Londonderry, Ireland to Londonderry, New Hampshire.
James Calderwood b Scotland went to Londonderry Ireland with wife abt 1724. He is known to have arrived in America in 1725 with wife Margaret and their two older children. Settled in English Range, North Beaver Pond, Londonderry, New Hampshire.
1a Jane b.Londonderry, Ireland M John Cushing a dau
2a John b. 15 feb 1725 Londonderry, Ireland
Source: Albert Hunt
Settled in Londonderry, New Hampshire, on what is called English Range, north of Beaver Pond, first buying 30 acres of land from James Rogers. also 16 acres of land granted from the town in 1726. also 45 acres of land granted from the town Jan. 4, 1729.
Source: History of Londonderry, New Hampshire (Copy made from history museum, Vinalhaven, Maine,( June 1993)
From the lands of Calderwood in the parish of Kilbride, Lanarkshire. The family were seated at Calderwood at a remote period. The last of the family were three brothers and a sister; and the former having quarreled with the priest of the parish fled to the Earl of Cassilis for protection, who gave them the farms of Peacockbank, and Moss-side, in the parish of Stewarton, and the Forty acre lands in Kyle. These three brothers were the ancestors of the present families of Calderwood. The sister remained in Kilbride, married a Maxwell, and became possessed of her father's estate.
Source: The Origin and Signification of Scottish Surnames by Clifford Stanley Sims
The Calderwoods are said to be of Scottish origin but emigrated to Ireland where John was born Feb 15, 1725, and the very same year his parents emigrated to Londonderry, New Hampshire.
Signers of the Petition, March 1785 to have the Commonwealth of Massachusetts relinquish claims of property to the inhabitants of the Fox Islands (Vinalhaven, Maine)
Signed, John Calderwood, Attourney for the inhabitants.
There were two petitions, the second one was known as the Calderwood petition and was the one acted upon. See Vinalhaven History
Among the signers of the petition were John Calderwood, James Calderwood, Samuel Calderwood, and William Calderwood.
Source: Kenneth Calderwood (my uncle)
Name: James CALDERWOOD
Given Name: James
Birth: in ,Londonderry,Antrim,Ireland
Death: 1750 in Londonderry,Rockingham,New Hampshire
Reference Number: 692
!BOOK:Town of Warren, Knox, Maine 974.153 H2e
Wish I had more for you but at least it's a help.
Sincerely, Mike Daigle