After graduation from the Massachusetts Institute of Technology (with degree in Mechanical Engineering), in 1886 Woodbury had great success painting up the New England coast and in the towns and beaches of Nova Scotia and exhibiting the results.

[citation needed] From January to June 1891 he was a pupil of the Académie Julian in Paris,[1] after which he went to Holland, where he studied the techniques of the modern Dutch painters.

Nevertheless, Woodbury maintained a close friendship with John Singer Sargent and a pleasant acquaintance with many of his contemporaries including J. Alden Weir and Childe Hassam.

[citation needed] He was president of the Boston Watercolor Society, and became associate of the National Academy of Design, New York in 1906 and a full member in 1907.

He maintained a strong and consistent vision in his more than fifty years of professional life and became a master of compositions of the coast and sea.

In the words of his son David, Woodbury "...painted what he saw, satisfied that what he saw was really there, all in proper relationship, checked and rechecked by endless reference to the real world".

Woodbury engaged in over 100 solo exhibitions throughout his career, and was included in all of the major invitational and juried shows throughout the country.