David Stimson grew up on Cape Cod, where he began working in boatyards in 1969 at the age of 15. A neighbor, Merton Long, taught him many tricks of the trade and showed him how to design and build boats in the traditional manner from a carved half model. 

Stimson worked in various boatyards on the Cape until 1977, when his brother and he started their own business, Stimson Brothers Boatworks. He brought the business with him when he moved to Boothbay in 1981, and began building and repairing boats in his parent's barn on River Road. 

Between 1981 and 1997 he built about 30 boats on the property and repaired and restored many more. In 1997, with no work in sight, Stimson accepted an offer to lead the construction of a 60-foot schooner at Gannon and Benjamin on Martha's Vineyard.

Stimson and his family returned to their property on River Road in 2002, and resumed boatbuilding and repair. Projects at River Road from 2002 to present include: 2003 restoration of 12-foot beetle cat sailboat; 2003-2004, designing and building of a 21-foot catboat; 2005 restoration of Old Town lake boat; 2006, designing and building of an 8-foot pram; 2008, designing and building of a traditional cedar skiff; 2010-2011 restoration of a 56-foot Alden schooner Bagheera; 2011 restored 33-foot Stadel cutter Constance; and present work – design and construction of 50-foot steel schooner. Stimson said some of the projects occurred concurrently with his employment as general manager of Boothbay Harbor Shipyard from 2005-2009.