Since there is a bit of interest right now about the war of 1812, I thought I would tell this peculiar story, which involves an ancestor on my mom's side, one Benjamin Darling.  

If your family has certain stories that go back a century or more, have you ever tried to ascertain whether they are historically factual?  I don't want to shock you completely, but it turns out the Darling clan has tended to embroider and exaggerate certain aspects of this one.  Nonetheless, I found quite a few different sources, in print and online, which collectively tell the tale inasmuch as it is understood.  

The Darlings were pre-Loyalist settlers in the area of Saint John, New Brunswick, having been merchant traders from Massachusetts who did business with the MicMac and others at their trading post up the Saint John River.  They settled there permanently in the 1760's.  After the major Loyalist migration to Saint John in 1783, they were somewhat reduced in social status it seems, since they were suddenly one of many reasonably well-to-do families rather than the big-fish-in-small-pond they had seemed before.  Darling's Island, a substantial holding in the Kennebecasis just south of Hampton, is named for them, but Darlings only officially held title to about 200 acres of it after the government surveyed and divided the island among the settlers.

A generation after the Loyalist settlement, Capt Benjamin Darling saw the war of 1812 as a chance to do some profitable business.  Consider the geography  and history of New Brunswick and coastal Maine; they were neighbours and relatives, and had all been British colonists until recently.  So it was an odd situation that these neighbours were suddenly, legally, at war with each other, when in every way they still had much in common.  

Here's where our family story diverges from the historical truth:  the story is that Benjamin mortgaged the Darlings Island farm to outfit his sloop as a privateer.  Privateers, of course, are legalized pirates, licenced by their own governments to harass and steal from vessels of a hostile government.  There were a lot of privateers licenced with letters of marque from New Brunswick and Nova Scotia, but in fact after a year or so New Brunswick stopped doing so.  Because there was too much fraud and chicanery going on.  What happened rather frequently was that a New Brunswick or Maine vessel would plan a "capture" with their friends from across the border.  The New Brunswick vessel would allow itself to be taken and its cargo seized.  Having acquired this booty, the Americans would generally auction off both vessel and cargo, for a quick cash sale.  Of course, a liquidation sale tends to be a bargain-hunter's paradise, the more so when it is held on short notice in a remote location.  So the American accomplices would purchase the vessel and cargo, then secretly split the profits with their Canadian cousins who had fought them so valiantly, then surrendered gracefully.  No one got hurt in these phony pirate raids, and the participants did very well.  The insurance companies, or sometimes the ship owners who were not in on the scheme, were the ones who paid the price.    

Benjamin Darling had his 78' sloop, the  Mary, built in Kingston, NB, an old village just west of Hampton, in 1813.  By the time she was completed, because of the numerous phony captures, New Brunswick had stopped issuing letters of marque, while Nova Scotia continued to do so for the rest of the war.  The Nova Scotia records are still online, and Benjamin Darling's sloop is not listed there, so I am sure she was never licenced as a privateer.  But she didn't need a letter of marque to continue the family business of carrying cargo down the Maine coast, she just needed a customer in a friendly destination.  And in fact there was one:  Castine.  

The town of Castine, located on Penobscot Bay about halfway down the Maine coast, was occupied by the British for most of the war.  That must have been awkward.  Castine is well into upper Penobscot Bay, a good thirty miles from the open Atlantic, so any vessels approaching or leaving would have to pass close by American settlements and there are a lot of coves and islands where an ambusher could hide in wait for them.  So it was a tricky business running supplies to the British garrison there, and they were in constant need.  In short, it could be a profitable but risky voyage getting in and out of Castine.  You needed a captain with nerves of steel, superb navigation skills and local knowledge to thread the sloop through this tricky, hostile waterway.  Instead, though, Benjamin and his business partner Gabriel Fowler hired Capt David McWatters.  

On its first (and last) voyage into Maine,  the Mary made it down the coast and into Penobscot Bay alright.  Coming from the Atlantic, they should have  entered Isle au Haut Bay, passed to the east of Vinalhaven and then Islesboro Island as they sailed north up East Penobscot Bay, and then passed to the north of Nautilus Island and made due east into Castine Harbour.  But Captain McWatters, whether by accident or design, evidently overran Vinalhaven Island.  Instead, he took the Mary into the West Penobscot Bay, never got anywhere near Castine, and in the fog off of Camden--which one reaches by sailing west, not east--encountered a rowing gig with six men aboard.  What happened next was the subject of litigation for several years thereafter.  

 Some witnesses claimed McWatters invited the men on the gig to pull up and board the Mary, either because he thought they were friends who would show them the way into Castine, or because he was betraying the Mary to the Yankees.  Others maintained they didn't wait for an invitation.  What is clear is that the six men were American revenue officers, and they boarded the Mary, imprisoned the startled and demoralized crew, and took their prize into nearby Camden Harbor.  

Now they didn't have radar or GPS, but they had friggin compasses. Sailing along the coast and being wrong about what town you're passing is one thing, but Camden and Castine are far apart and the compass bearings, not to mention distances and landmarks involved in reaching them are so different that it's hard to conceive the kind of incompetence that could make this an honest mistake.  Sure enough, the Mary and her cargo were sold at auction in short order, and Messrs Darling and Fowler were left to argue things out back in Saint John with their insurance company and the hapless captain, who like the rest of the crew was home safe shortly after their misadventure.    

 After a couple of years, in fact, the courts decided that McWatters had not been in collusion with the Americans and ordered the insurance company to pay out the claim which Darling and Fowler had made for the loss of the Mary and her cargo.  A contemporary newspaper article in the Saint John Recorder with the slightly exasperated title "Sloop MARY--Again" (see image below) tells a tale of McWatters' treachery according to Mr Fowler; however the story was evidently discounted by the courts, and its details seem to conflict with other sources.  But the unnamed insurance company agent quoted offers the sage advice to all and sundry "I think you will do well to keep clear of Castine risks." 

 But according to our family legend, the whole episode had been particularly disastrous for Benjamin Darling because he had mortgaged his Darlings Island farm to build and outfit the Mary, and ended up losing not only his brand-new sloop on her first voyage, but the farm as well.  I guess that's why we're not rich.  The Darlings, as a whole, became modestly successful, respectable farmers and merchants in the Saint John area, while the Fowlers are one of the most famous New Brunswick families.   

I found another interesting footnote to the story, concerning the bad luck of the American revenue officer who led the Mary's captors.  He was badly injured in another skirmish with a British vessel six months later, lost a hand as a result, and was pensioned off to a life of poverty. Amazingly enough, his name appears with that of the Mary in the proceedings of the US House of Representatives some twenty-five years later; he was still trying to obtain a share of the proceeds from the sale of the captured booty!   

The port of Castine, of course, was returned to American control at the end of the War of 1812.       

 That war wasn't the last episode of military hostilities between the US and Canada, although the Fenian raids of the post-Civil-War era were not official US government ventures.  But hey, mostly we've gotten along pretty well.