The Tiffanys were wanderers. For six generations leading up to Gideon, each generation had been born in a different place. Gideon's father, also Gideon, was born in Attleborough, Massachusetts but moved to New Hampshire before the Revolutionary War. Gideon, the son, was born in Keene, New Hampshire in 1774 but moved with the family to Hanover, New Hampshire when he was about 12. When he finished school, he became a printer, probably with his eldest brother, Sylvester, in Troy, New York.

In 1794, he learned from his brother-in-law, Davenport Phelps, that the position of King's Printer for Upper Canada was available in Newark (Niagara-on-the-Lake). In November, he was appointed and in December published his first edition of the Upper Canada Gazette. He also started job printing, publishing in 1795 a pamphlet by Richard Cockerel, the first non-government publication in Upper Canada. The following year, he was joined by Sylvester as his assistant. Unfortunately, because they had been born in the US, the government began to regard them as pro-American. As a result, Gideon and Sylvester resigned in 1797 and were succeeded by Titus Simons. Simons knew nothing about printing and the government had no press, so the Tiffanys continued to print the Gazette from their print shop. This situation continued until the Gazette was transferred to York (Toronto) in 1798.

The following year saw the Tiffanys begin publication of Upper Canada's first independent newspaper, the Canada Constellation. By 1800, Gideon was publishing the Constellation alone, but not for long, because by the next year he had given up printing for good.

He used the money he had made from printing and, with another brother-in-law Moses Brigham, bought land in Delaware Township from Ebenezer Allan. In November 1806, possibly as a solution to a legal problem, Tiffany, Brigham and Allan had the whole property conveyed to Gideon's older brother, Dr. Oliver Tiffany, who was living in Ancaster. Gideon and Brigham continued to live in Delaware and operate the two sawmills on the property for Oliver. Gideon himself bought additional land in the surrounding area. He continued to live quietly except for a period in 1837 when he briefly got involved in a reformist movement, was prosecuted, acquitted, and freed. His neighbours found him full of old stories, and liked and respected him. He died in 1854, and is buried in the Tiffany cemetery in the village of Delaware.