Dickerson sailboats for sale

Buying a used Dickerson: one yard's whole history, not a scattered brand

Every used Dickerson came out of the same Chesapeake Bay yard - Church Creek, then Trappe, Maryland - across three ownership eras and a wood-to-fiberglass transition, rather than from a brand name spread across builders with inconsistent standards. That consistency cuts a specific way for a buyer: the question isn't which factory built a given hull, it's which era of the one factory built it, since the yard's construction methods, keel design, and even its cabinetry assembly changed markedly between Bill Dickerson's hand-built wooden ketches and the fiberglass cruisers designed under later owners. Matching a hull's construction era to what a buyer actually wants - a traditional full-keel wood boat versus a later fin-keeled fiberglass cruiser, for instance - matters more here than chasing a specific model.

Which era to target

The earliest boats, including the Simplissima-class 26s and 32s and the original 35-foot hard-chine ketch, were wood, built with enough shop-floor variation between individual hulls that two examples of the same model were rarely identical. Tom Lucke kept building wood 35s and the 40 through the late 1960s before concluding fiberglass had proven itself; 1974 is the hinge point, when the wooden 40 was retired for a new fiberglass 41 and the 36 moved into fiberglass the same year. Boats from the Ted Reed and George Hazen era that followed mark a further design break: the 1981 cruising 37 replaced the marque's long-standing full keel with a fin keel and skeg-hung rudder, and the 50, added in the early 1980s, extended the lineup's top end. A separate, unrelated 37-foot racing sloop designed by Bruce Farr also dates to the early 1980s - a different boat entirely from the cruising 37 despite sharing a length and an era, so it's worth confirming which 37 is actually on offer before assuming either one's characteristics apply.

Navigating the lineup

The clearest split for a buyer is wood versus fiberglass: anything from before the mid-1970s transition is a wood boat with the maintenance profile that implies, while the 36, 41, 37, and 50 represent the yard's fiberglass-era work. Within the fiberglass boats, the 37 and 50 came out of the same high-performance push that followed Ted Reed's 1978 purchase of the company, while the Farr-designed racing sloop sits apart as a boat built for racing rather than cruising. The full model directory on this page breaks out the specific years and lengths across the range.