The Timberwind was built in 1931 on Union Wharf in Portland, Maine. She was built to the highest standards to insure the comfort and safety of the men who sailed her. The schooner was built in Maine for Maine duty, and since her launching in 1931, she has never left Maine waters. Built to carry pilots to and from ships entering or leaving Portland harbor, she was constructed ruggedly using sturdy white oak frames and planks for seaworthiness through years of storms and icy Maine winters. As launched, she was bald-headed, had no bowsprit,and had her main cabin located aft with a large hold amidships.

Timberwind's original name was the Portland Pilot and she served as the pilot boat for the harbor of Portland from 1931-1969. Portland Pilot and her crews faced countless vicious winter northeasters when green waters as well as spray coming aboard froze to the rigging and had to be chipped off in order to maintain stability. She always met the challenge although in one particular bitter storm, on February 16, 1958 she suffered her only casualty and was thought lost herself.

For thirty-eight years, twenty-four hours a day and in all weather conditions, Portland Pilot was on call. When she wasn't on station fifteen miles offshore, she was in at the dock taking on stores and readying for her next shift. She was finally replaced with a steel power boat in 1969, but to this day she is fondly remembered by the men who worked on her out of Portland.

They enjoy coming to Rockport to see her, and although they may chuckle at her fancier paint job and taller rig, they see that she is the same vessel underneath and are pleased to see how well she's cared for.