After a brief stint at the Boston Museum of Fine Arts School (Sept. to Dec. 1910), which proved to be too much for RSW and high school
friend Joseph Cowell to manage, Woodward left Boston for Buckland (MA). There he would join the household of his Aunt Attella and Uncle
Bert whose Pine Brook Farm housed 14 others, including RSw's grandparents and cousin Florence. He would co-op an old diary shed in front
of the farm and with the help of family convert it into a studio he called "Redgate".
The plan was for RSW to apply his drawing skills towards becoming a commercial artist. It was the "golden age of print" leading to high demands
for illustrators and calligraphers. Also, one of the country's premiere engravers, John Edwell, resided near by and RSw hoped to take advantage
of the proximity. However, while RSW had a number of high-profile clients, in the end, the selling his services business-model would prove to be
unsustainable to suit his needs and high cost of care (amounting to about $3,900 in today's dollars).
In 1916, after seeing his first grey hair, he pursued his long-time dream of being a professional landscape artist. He started painting in oil on
canvas and after a couple years and some encouragement from local artist Symons Gardner, RSW entered his first professional exhibition at
the Boston Art Club in 1918 receiving high praise from critics.