It was during this period that Wood began having his most famous works published, working with companies who printed inexpensive color reproductions of works by both contemporary artists and the Old Masters. It was Wood's paintings of the changing seasons around Woodstock that sem to have captivated the public, and his reproductions were immediately popular. The most successful of Robert Woods' Catskill scenes, "October Morn," sold more than one million copies in less than two years for the Donald Art Company. Across America, homes, offices and motel rooms were decorated with his reproductions. These inexpensive paper prints made Robert Wood the most famous American landscape painter of his era.

Wood's rustic studio in Woodstock was located out in the forest, surrounded by maples and elms and a quiet brook. He immortalized this rustic setting in hundreds of paintings, especially ones that depicted the bold colors of autumn. In his artistic oeuvre there are also many depictions of the Catskill Mountains' landscape enveloped in snow, as well as spring compositions with lilacs and blooming apple trees.

From Woodstock, Wood went on sketching trips to New Hampshire, Vermont and along the Maine coast. These subjects are also represented among his Eastern scenes, but are much rarer than the hundreds of paintings done of the Catskill Mountains.

Wood seems to have left Woodstock due to difficulties with his romantic relationship with Rose Wood and her mother, who were determined that the artist should share their religious convictions. So, according to Larry Kronquist, Wood left the two women in the cottage in the woods and returned to the art colony of Laguna Beach.