I'm having trouble with the terminology here. Chesapeake Bay is the domain of several distinctive boat types - the skipjack, the bugeye, the log canoe, the pungee, and the deadrise come to mind. Most of them were/are used for harvesting oysters and/or crabs. I've seen plenty of trawlers coming into and out of Norfolk, Hampton, and Newport News (where I used to live), but so far as I can recall there's nothing about them that's noticeably different from trawlers operating out of other ports. I think most of them do their fishing well offshore, in the Atlantic. The boat types that are generally associated with the Bay operate in shallow water. (Most of the Virginia oystering nowadays is done by 1- or 2-man deadrise power boats. The waterman stands on the rail with a pair of "oyster tongs" and literally scoops the oysters off the bottom.)
The Model Shipways skipjack Willie L. Bennett is a nice kit - great for anybody who wants to get into serious scale ship modeling for the first time. I've also seen a line of wood kits by another firm, whose name escapes my halfzeimer's-afflicted brain at the moment. This firm (whatever it was) made a skipjack, a bugeye, and a deadrise - and maybe some others. They looked to me like pretty good kits, but I haven't seen them for a while. I fear they may be out of business.
The only plastic kit for a Bay boat, to my knowledge, is an old, old skipjack by Pyro. It may still be around (maybe in a Lindberg box). As I remember it wasn't too bad, if you got past the injection-molded furled sails.
I'm afraid I haven't helped much. If you could be more specific some more relevant light bulb might light up in my head. Good luck.
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