I travel a lot on business, mostly in the United States but occasionally Canada or the Caribbean. Most of us, those that have traveled to these places, if dropped in Irish Bayou (LA), Theodore (AL), Asheville (NC), Bayonne, or Charleston--without even looking around but allowed to overhear a few moments of conversation, would offer a fair guess. We'd do best if it was a dinner or pub--down town it's too common to meet nothing but transplants. "I's just playin' wit you" or "Hows you doin'" and we'd relax and answer in kind, according to our ability with the local idiom.
I think I could be dropped anywhere in the Chesapeake Bay, look at a few boats, glance at a marina, maybe talk to a sailor or two, and I could place myself within 20 or 30 miles, without navigational aids or asking geographical questions. Things are just different.
(Yup, I'm going to generalize. I'm allowed.)
The Northern Bay (Elk River to Rock Hall). Powerboat country. Lots of express cruisers, though they fly away the week after Labor Day. Poker runs start up here, where the water's smooth...ish. The parade of express cruisers and their sharp wakes can make life anywhere near the main channel north of the Sassafras down right unwelcoming.
Crab boats on the open Bay are a bit smaller than further south with less expensive roofs for carrying traps; the water being smaller I doubt they have to carry so many so far. The creeks are worked by any sort of skiff, mostly trot lines rather than pots. Crabbing is less anyway, as the water is basically fresh north of the Sassafras. They don't work oysters; they're all long gone this far north, even though Rock Hall was probably named for the mountains that used to come in for packing. Oysters were often called "rock" they hauled a lot of them in what became an unsustainable fishery. Sailboats are often smaller and generally not headed far, unless they're just passing through. Most local sailors think a 25 mile day is something. The waters feel more like a large river or reservoir than something that is connected to salt water. It isn't really salt, hardly at all.
There's is some cruising, but it's smaller and different. The western shore is dominated by the Aberdeen Proving Grounds (often on weekdays the Aberdeen safety patrol will chase you from their boundary waters, marked on the charts as a restricted area) and Baltimore (way too urban for may tastes, but perhaps that's a reflection of the time I've spent working in the dirty industrial waterfront that dominates the approach to the city. The Inner Harbor is nice; like staying in a nice downtown hotel.
Cruising is an overnight. Further south, we do that after work.
Ego Alley (the Annapolis city dock) is in a league by itself. Like the Inner Harbor; smaller, more sailor-oriented, but just as down town. The local name explains.
The waterman's boats are getting bigger as you move south, as is the water. Some dredge for clams, but most work crab pots. Pound nets become commonplace, an occasional hazard to navigation and certainly a hindrance to recreational fishing (they catch all the damn fish, scooping everything that comes by, day and night). Even shallow draft boats stay in 20 feet of water; the crab pots near shore are thick.
In the summer at least, it has an urban or at least horse country feel to it. Crowded and sometimes show-offish. In the winter, 70% of the boats haul out and the rest stay tied up. It feels like you're little bit further south; at least the crowds are gone. In the summer, you're always racing somebody, or at least heading the same direction. Would-be racers and the folks that watch them think nothing of crossing within a boat length. A sharp watch in the genoa blind spot is obligatory, but it's amazing how many people don't feel so obligated; watch yourself on a nice weekend, just like city traffic. Folks run the red lights.
Weekend cruising. Sometimes 2 nights, if they're retired.
Southern Bay. Deale to Cape Charles. Cruisers go farther down here, partly because they must and partly because they can. It's more adventurous country. It's common to meet to a cruiser that hasn't been to a marina in a week. If you've been out for 2 weeks, your in good company. Others still hop, to be true, on the western side. I guess that's why like eastern side better.
The sailors are better cruisers. They get more practice. They seem more self-reliant; they have to be. I'm not saying that they're better sailors-- racing is an Annapolis thing-- but there's a lot more to cruising than just sailing. The channels aren't marked so well down here, the shoals move around, and the guidebooks miss a lot. I like it better that way.
Boats are more apt to have gear hanging off of the rail: if they're cruisers, bicycles, jerry cans, and tarps; if they're fishermen, piles of crab pots, oyster dredges, or even yawl boats for pushing a Skipjack. The menhaden boats are a givaway; in the haze, I often smell them before I see them.
Oysters aren't called "rock"; "they's arsters, that's what we druge in this wata." Not "hearabouts"; that would be farther south and farther inland. Fishermen, particularly in the small towns, get harder and harder to understand. It isn't a southern dialect, it's a Bay dialect. I like it. Just slow down and listen. They don't respect fast so much; they respect steady.
It's rural. You may not see but one or two cruisers on a summer day, and you won't see any in the winter.
Sherlock Holmes bragged he could identify the origins of any Londoner within a few blocks by minor quirks of their speech. They think I can identify a Chesapeake cruiser, or at least the collection of boats, within 30 miles, no problem. A quick glance of any marina is a giveaway to the trained eye.