The artists Aldro Hibbard, Antonio Cirino, Paul Strisik, Anthony Thieme, W. Lester Stevens and Harry Aiken Vincent were contemporaries closely tied to its early days.
In 1921, a group of artists that were attracted to the seaside village of Rockport decided to form the association.
RAA was originally established as an artist cooperative for art lovers and creators.
In the year of 1929, the Rockport Art Association had been placed in its permanent location of an Old Tavern building on Main Street.
The RAA is also known to hold several special events, exhibitions, and educational series Such as artist painting demonstrations and plein air workshops, a National Art Exhibition feature diverse works from across the country.