We anchored in Ames Cove(20' of water below our yawl here), last season to visit Dark Harbor. After the civil war, the first rusticators showed up on the coast of Maine. In this area, before 1900, an opulent summer colony with a "social preeminence" beyond even that of Bar Harbor set down roots in Dark Harbor.
I've not read why this area had such a draw for the few people with the means to create their own summer utopia but I suspect Gilkey Harbor was the reason. A large protected body of water for sailing races and a shoreline with near infinite spots for builiding the "cottages" of the day. Ames Cove was the perfect place to build the club, the meeting place for meals and socializing. These Turnabouts are moored off the Tarrantine Yacht Club. We tied our dinghy up at their docks, and went ashore there(it's private, but I don't mind). A better place is Pendleton Yacht Yard if there's enough water for your dinghy(it's tidal).
I'm a history buff, especially poking around coastal Maine on our boat. Even more fun though, is to compare then and now in places like Dark Harbor. Dark Harbor on this late July day, was like walking onto a movie set. That's not unusual, most of the coast to varying degrees, goes through this summer set change. Small home type summer businesses had hand lettered signs out front. A magic markered sign in front of a home bakery said, "Sold Out" In this little shop, you could try on a summer dress and enjoy a cappuccino inside.
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Dark Harbor proper, is just a cleft in Islesboro and exposed in any wind. It's visible here beyond the tidal pool in the little village center.
The busiest place was the Dark Harbor Shop that was selling ice cream. Kids in tennis whites, nannies with small charges in tow, all were coming out with cones.
Different today for sure. But maybe more in the category of the more things change,... The big hotels are gone, the Dark Harbor Hotel survives as a casual(if expensive) B&B. There were 10 "stores" in those Gatsbyesque days to keep the guest happy, today, you'd have to drive from here to get any provisions. Some of the old cottages still line Ames Cove and up Bracketts Channel, but they quiet these days in comparison. That's the biggest change. The old Maine here was a more raucous place in summer than it is today.
These days, things are still in comparison. I imagine places like Dark Harbor in mid winter. You won't hear the word "winter" used out there in February, as anything but the noun.