The bugeye is a distinct type of Chesapeake Bay sailing vessel developed for dredging oysters in the years before skipjacks appeared.

In 1820 the state of Maryland banned the practice of dredging for oysters, but in1865, the law was relaxed. The use of powered vessels remained banned, however, and remained entirely prohibited until 1967, when powered dredging was allowed two days of the week. Opening the Chesapeake to oyster dredging after the Civil War created a need for larger, more powerful boats to haul dredges across the oyster beds.

The first vessels used were the existing sloops, pungies and schooners on the Bay, but none of these types was ideally suited to the purpose; pungies and schooners were too deep in their draft to work the shallower waters of the Bay, the schooners and sloops had bulwarks too high to facilitate handling the dredges, the relatively complex rigs of all three types required uneconomically large crews of skilled sailors, and the vessels themselves were relatively expensive to build and maintain.

The log canoes had none of these disadvantages, but were too small to successfully haul dredges. The result was the development of bugeyes, enlarged and fully-decked log canoes with a permanently stayed rig. Bugeyes were typically 45 to 55 feet in length on deck, shallow-draft and equipped with a centerboard. Early examples were double-ended, though a few later bugeyes had round or transom sterns. The rig was typically that of a two-masted ketch with jib-headed (triangular) sails, though the masts were raked and named fore and main in schooner fashion.

Log construction was a hallmark of Chesapeake boatbuilders. Builders would flatten the sides of the logs and join seven, nine, or even eleven logs side-by-side and hew them to shape with axe and adze. The hulls of bugeyes were fashioned from solid chunks of wood in this manner. The largest and longest log was used for the center, and the hulls were sharp at both ends—like an oversize canoe. Simple locust treenails or iron drifts fastened one log to the next.

Edna E. Lockwood is typical of this classic regional method of boat construction.

Over the next twenty years, the bugeye became the dominant type of vessel employed in oystering, but in 1893 construction of new bugeyes began to decline and by 1896, the skipjack began to appear in numbers. Skipjacks were less expensive to build, operate and maintain and were suited to dredging for oysters. No working bugeyes appear to have been built after 1918, but bugeyes continued to be employed in oystering and freighting until the middle of the 20th Century, albeit in ever-decreasing numbers. The origin of the name bugeye is obscure.