[1] His mother died when he was very young, and his father removed with him to Troy, New York when Winchester was 10 years of age.

After receiving a preparatory education at the Clinton Liberal Institute, in Clinton, Oneida County, New York, and the Troy Conference Academy, in Poultney, Vermont, Britton went to Union College, from which he graduated with honors.

He dropped his legal studies in 1848, embarked for Aspinwall, Colon, crossed the Isthmus of Panama, and arrived in San Francisco, California aboard the steamer Crescent City.

He was very successful in mining and other business enterprises in San Francisco, but after accumulating a small fortune he lost nearly every dollar of it by fire.

He was elected Kings County District Attorney in 1871, but was removed in 1874 by Governor John Adams Dix for alleged malfeasance in office.