In 1880, Benson began to study at the School of the Museum of Fine Arts, Boston under both Otto Grundmann and Frederic Crowninshield.

To encourage educational activity, Benson's parents gave their children a weekly allowance to foster independent study and hobbies, such as Salem's Hamilton Hall dance classes, Lyceum lectures[6] or equipment for photography.

[5]: 16–17  To his good friend Dan Henderson, he wrote of their childhood adventures: "We used to spend our Saturdays chasing coot and old squaws in Salem Harbor.

Then, after working hard all day to get one bird, in we would assemble at Sam Shrum’s or mine and chew the rag until we were so sleepy we could not hold up our heads.

Both sons may have been influenced by their mother, Elisabeth Poole Benson, who Frank once remarked, had "a little room" on the top floor of their house where she would go to paint and "forget about the rest of the world".

[5]: 8  He began his studies at the School of the Museum of Fine Arts, Boston in 1880,[5]: 263  and there befriended Joseph Lindon Smith,[5]: 20  Robert Reid and Edmund Charles Tarbell.

He capitalized on Monet's color palette and brush strokes and keenly depicted "reflected light", yet maintained some detail in the composition.

[5]: 263 [8] The spring of 1889 he began teaching antique drawing at the School of the Museum of Fine Arts, Boston and in 1890 became head of the Painting department.

Students were assessed on the basis of their skill and placed at the appropriate level (from low to high): Hale had a class for beginners, Benson concentrated on how to depict figures while Tarbell covered still lifes.

They are images alive with reflections of youth and optimism, projecting a way of life at once innocent and idealized and yet resonant with a sense of certain, selective realities of contemporary times.

[14] He gained favorable attention in his first showing at the Society of American Artists in New York, with a piece that suggested the influence of academic Realism.

[15] At the suggestion of his friend Joseph Lindon Smith, Benson spent several summers in Dublin from 1889 to 1893,[5]: 26  where he painted with and was influenced by Abbott Thayer.

[15] It was only after joining the "Ten American Painters" in 1898 that Benson shifted from the decorative painting of murals (for the Library of Congress) and allegories, to a genuine interest in plein-air Impressionism.

The family spent summers in New Castle, New Hampshire from 1893 to 1900,[5]: 263  where Benson made some of his first Impressionist paintings, such as Children in the Woods and The Sisters.

[10][15] After New Castle, the Bensons spent their summers on North Haven Island in Penobscot Bay in Maine at Wooster Farm.

Near the house was an old orchard, large fields provided plenty of space for the children to play and for a garden, and the property stood beside a wooded area.

"[10] A critic said of Benson's work: "It is impossible to believe that mere paint, however clearly laid on, can glow and shimmer and sparkle as does that golden light on his canvas.

[14] In 1898 Benson and nine other artists including William Merritt Chase, Thomas Dewing, Childe Hassam, and J. Alden Weir formed "Ten American Painters".

[25] To date the highest price brought at auction for an oil painting by Benson is $4.1 million, realized at Sotheby's in 1995.

The original Benson was eventually obtained by a collector named Donald Purdy, and later by the New Britain Museum of American Art.

The fake Benson painting remaining with the Detroit Club was finally sold for $38,500 to an attorney and his wife, at an auction held by Christie's in 1986.

A lawsuit was filed against Christie's, alleging negligence and/or fraud;[29] but a Delaware Court ruled in favor of the defendants,[30] opining that the auctioneer's fiduciary responsibility was with the seller rather than with the purchaser.