He later enrolled at the Académie Julian in Paris where artists such as Bouguereau, Lefebvre, Constant, Doucet and Boulanger taught students from all over Europe and America where he spent 2 years of schooling in Paris.

Upon returning to America, Benson opened a studio and began painting portraits of family and friends. An oil painting of Ellen Perry Peirson, dressed in her wedding gown is representative of this period.

It demonstrates not only the academic techniques he had come to possess but also his own growing emphasis on the effects of light. The painting exudes the warmth that existed between model and artist. More than a likeness, it is a study in serenity.

Perhaps it was of a work such as this that Benson was thinking when he said, "The more a painter knows about his subject, the more he studies and understands it, the more the true nature of it is perceived by whoever looks at it, even though it is extremely subtle and not easy to see or understand. A painter must search deeply into the aspects of a subject, must know and understand it thoroughly before he can represent it well."

Benson was appointed as instructor of antique drawing at the Museum School in Boston in the spring of l889. Benson cherished his role as teacher and was held in high esteem by his students, many of whom called him "Cher Maitre." Reminiscing about his long career with the school Benson once said, "I may have taught many students, but it was I who learned the most."

In 1890, Benson won the Hallgarten Prize at the National Academy in New York. It was the first of a long series of awards, that earning for him the sobriquet "America's Most Medalled Painter." In the early years of his career, Benson's studio works were mostly portraits or paintings of figures set in richly appointed interiors. His first daughter, Eleanor, poses with her cat. He had a steady influx of portrait commissions, yet it was in his outdoor works that gave Benson his greatest pleasure.

Beginning in 1889, Benson and his family spent his summers in Dublin, New Hampshire, a little summer colony at the foot of Mount Monadnock. Working under the influence of the Dublin artist Abbot Henderson Thayer, Benson's numerous works included, Summer, a painting posed for by his wife and the murals that he did for the Library of Congress. These ethereal works stand in marked contrast to Benson's later plein-air paintings of his daughters which were praised by contemporary reviewers for being the embodiment of the "fresh, appealing American girl." For the most part, Benson's outdoor paintings of the 1890s tended towards landscapes and marines. Only occasionally did he venture into figural work.

In the latter half of the 1890s, Benson summered in Newcastle, on New Hampshire's short stretch of seacoast. It was here, in 1899, that Benson made his first foray into impressionism with Children in the Woods and The Sisters, the latter a sun-dappled study of his two youngest daughters, Sylvia and Elisabeth.

This painting was one of the first works that Benson hung at an exhibition with nine friends. The resignation of these ten illustrious artists rocked the American art establishment but, the catalogue for their first exhibition was titled, simply, "Ten American Painters." When, in 1898, the three Bostonians and seven New Yorkers began to exhibit their best work in exquisitely arranged small shows, the group (dubbed by newspapers, "The Ten" ) quickly became known as the American Impressionists, a bow to the style of their French predecessors. Held annually in New York City, the group's yearly exhibitions usually traveled to Boston and were occasionally seen in other cities.

Benson's association with other members of the group such as Childe Hassam, Thomas Dewing, William Merrit Chase and J. Alden Weir, only reinforced his growing emphasis on the tenets of Impressionism.

As he later said to his daughter Eleanor, "I follow the light, where it comes from, where it goes."