In 2000 and 2001, the International Pirates joined up with the Chamber of Commerce of Westport, Washington at the annual Crab Races to entertain all visitors with their musical skills, humor, and pirate costumes. In 2002, Karen and Mac McLellan of Pic-A-Roon Pelican at the Westport Marina created the beginnings of a pirate festival. The Lady Washington became a "character" ship in a new pirate film by Disney and an era was born. With lots of energetic volunteers each year, they grew the event for the next five years until a pattern emerged and the whole town gladly became "Pirates" once a year.

Lou Burrell of Granny Hazel's Candy and Gifts suggested the name Rusty Scupper for the event ID. Larry Smith created the face and logo of Rusty, designed the shirts, and led the Rusty Scupper (Westport) Pirates Band and for seven years Arlene Smith wrote a chapter a year on Rusty's life. A core group has made this possible year after year via the Rusty Scupper's Pirate Daze Board of Directors and the committees they have established.

Every year, a person who unselfishly supports all of Westport is given the honorary title of Grand Marshall and leads the parade. 2015 brings us to the 13th year of RSPD and onto our third captain and hundreds of volunteers who have altogether brought us this far. Vendors, entertainers, dozens of pirate groups, big ships and little boats, and the people who attend have made this one of the largest pirate festivals on the western coasts. We welcome those in costumes and those in their daily apparel and look forward to seeing many more each successive year as participants and volunteers.