His career consisted of being a farmer and thoroughbred dealer in Toronto Township.
He was chosen as a Liberal candidate in Peel County to contest the general election for the House of Commons in 1891 against the sitting Conservative member William Armstrong McCulla.
Featherston won that election with a 54 majority, in what has been described as a "keen and exciting contest."
That election was declared void; a by-election which was held on February 11, 1892, gave Featherston a majority of 133.
The next election Featherston participated in was against A. F. Campbell, publisher of the Brampton Conservator.