Halloween is on the horizon so let’s kickoff the season by retelling two of my favorite Wiscasset ghost stories. You’ve probably heard Washington Irving’s “The Legend of Sleepy Hollow;” the story of Ichabod Crane and the Headless Horseman. What you might not know is Wiscasset has its "Legend of the Haunted Gully" featuring a headless Indian warrior.  

Our story begins with a bloody skirmish between the early English settlers and the Natives that took place in the late 1770s. The hostilities were the result of the Indians becoming increasingly wary of the land-hungry English who were encroaching on their hunting grounds. One crisp autumn morning a group of them decided to take matters into their own hands by launching a surprise attack on the whites at Wiscasset, which was then a part of Pownalborourgh. A painted war party paddled their long canoes from Jeremy Squam, known now as Westport Island, and landed in a secluded cove on the Wiscasset shore; their target being Williamson’s Garrison, a timber fort overlooking the river. Armed with tomahawks, knives, bows and muskets the warriors crept quietly through a wooded ravine surprising two men setting pigeon snares. Seeing the Indians, the pair dropped everything and ran for their lives. Only one reached the safety of the stockade, his comrade dying at the hands of the warriors. In the battle that followed the Natives charged the stockade and were met with the blast of a cannon at point-blank range that sent the warriors retreating to the woods. After the smoke had cleared the settlers made a ghastly discovery outside the fort; the bloodied, headless body of one of the fearsome warriors, his head having been blown off by the cannon blast. 

The ravine where the headless warrior was found has been known ever since as the Haunted Gully because as the legend goes, it’s here, on moonless nights that the restless Indian’s spirit, tomahawk in hand, can be found roaming the gully searching for a head to replace his own. The story of the Haunted Gully first appeared in print in 1859 when Rufus King Sewall of Wiscasset included it within his book “Ancient Dominions of Maine."

An attorney by trade, Squire Sewall collected a good deal of history concerning Maine’s earliest days. His research included an unusual theory of the so-called Native American meaning of the name Wiscasset. Sewall’s research led him to theorize the name Wiscasset had something to do with the supernatural; that is to say, the place where departed souls gathered and appeared at a certain time of year.

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It was a treat recently to hear Sean Rafter retell the strange, some might say supernatural story of Moses Carlton, one of his early Wiscasset ancestors. Sean shared the story during the summer gathering of the Wiscasset Fire Society. I can’t tell the story of Moses Carlton as well as Sean, but it goes something like this: As the 18th century gave way to the 19th, Moses Carlton could say without boasting he was the richest man in Wiscasset. Squire Carlton owned more sailing ships than any of his competitors. By the time he’d reached middle age he’d earned a fortune shipping lumber, salted cod and other goods to the “Sugar Islands” of the West Indies. It was here that these goods were exchanged for molasses, and rum to be sold at a huge profit on the return voyage. 

When one of Moses Carlton’s ships returned home, the gold and silver coins earned from the voyage were nailed in kegs and rolled from the waterfront to the Carlton mansion, the beautiful home with the rising sun over the door on High Street. There under Carlton’s watchful eye, the kegs would be lugged to the cellar, and emptied into his strong box. Moses Carlton once had a Spanish gold doubloon fashioned into 10 brooches, one for each of his seven daughters, and the other three for the wives of his three sons.  

You could say life was pretty good for Moses Carlton and Abigail his wife. They enjoyed the most luxurious furnishings, their dinner table offering the finest food and spirits. Moses Carlton had every reason to believe his refined living would continue the remainder of his days. This indeed might have happened if his vanity and pride hadn’t caused him to foolishly tempt fate.  

One day as Moses Carlton stood on the wharf admiring his many ships, he removed a handsome gold ring from his finger and carelessly flung it into the harbor. “There is as much chance of me dying a poor man as there is of ever seeing that ring again,” he boasted aloud. Well, a few days later when Pendy the maid was serving dinner at the Carlton table, to everyone’s astonishment the same gold ring was found inside the belly of the baked fish! 

The ring’s mystifying return to its owner proved to be a very bad omen for Moses Carlton. Soon after this extraordinary occurrence Congress passed the Embargo Act of 1807 prohibiting sailing merchants like Moses Carlton from exporting their goods. Things went from bad to worse a few years later during the War of 1812 which brought merchant shipping to a standstill. As for Moses Carlton, it’s said he stood weeping bitterly on the same wharf where he once foolishly tossed his ring into the water.  

Although he lost much of his material wealth Moses Carlton learned a powerful lesson. For the remainder of his long life he remained steadfast and true to Abigail and his family. He died in 1857 at the ripe old age of 90; his mortal remains rest at peace in the Ancient Cemetery on Federal Street.   

Phil Di Vece earned a B.A. in journalism studies from Colorado State University and an M.A. in journalism at the University of South Florida. He is the author of three Wiscasset books and is a frequent news contributor to the Boothbay Register/Wiscasset Newspaper. He resides in Wiscasset. Contact him at pdivece@roadrunner.com