Bosley's family moved to Winchendon, Massachusetts, in 1883, when his father purchased a foundry there. Bosley's interest in art developed during high school. Upon graduation, and over his father's objection, he entered the Museum of Fine Arts School in Boston where from 1900 to 1906 he studied under Edmund Tarbell, Philip Hale and Frank Benson. The Paige Travelling Scholarship awarded him by the school enabled him to continue his studies in the European museums.
Upon his return in 1908, he married a fellow art student, Emily Linzee Sohier, and the following year the couple settled in Lincoln, Massachusetts; they relocated to nearby-Concord in 1922. Bosley taught at the Abbott Academy in Andover, and initiated and directed the art department of the Groton School in Groton, Massachusetts. In 1913, upon Tarbell's retirement, he was appointed director of the department of painting and drawing at the Boston Museum School. He taught there until 1931 when he resigned over the school's change of focus when it added foreign, modernist artists to its faculty.
Bosley kept a studio in Boston until 1924 when he built a studio at his home in Concord. In 1926, after spending a summer at the artist's colony at Peterborough, New Hampshire, he purchased land in nearby-Piermont, and established his summer painting base there.
Exhibitions of his work were held at the Guild of Boston Artists in 1918, 1924, and 1926; at Boston's Coply Gallery, 1929, and at Doll and Richard's Gallery.
Bosley's portraits, landscapes, still lifes, and interiors--often settings for figure studies of upper class women at leisure--were characteristic of the realistist tradition associated with Edmund Tarbell, associates and other students of the Boston Museum School.
