After relocating to Boston in Massachusetts Bay Colony a year later, he painted miniatures on ivory, which was a very popular portrait style at the time.

Ramage joined "the Loyal Irish Volunteers", in December 1775, a military unit defending Boston on behalf of The Crown.

While in Halifax, he left Ball behind in Boston, to marry a woman whose real identity was never revealed, only known as "Mrs Taylor".

While in New York, he was promoted as a second lieutenant for the City Militia and joined St. John's Masonic Lodge.

[2][3] After serving as second lieutenant, he decided to work on miniatures in the artistic, but small community of New York.

The sitting took place 3 October 1789, possibly at Washington's official residency at the Samuel Osgood House in New York City.

For ivory, he used delicately shaded cross-hatching overlapped with fine and smooth linear strokes to model his subject's faces.

His original plan was to go to Quebec to find encouragement from Lieutenant-Colonel George Beckwith, and an acquaintance from Boston, Thomas Aston Coffin.

He was discharged from jail after a month, due to the grand jury favoring his loyalism during the American Revolution.

Want of money has been the only thing that has Prevented me from flying to your Arms, as I have never been three weeks at a time in health Since I came to this Place, by my fretting and anxiety of mind for you and my Poor dear Children."