Dark Hollow and other Spooky Tales

October 30, 2020

This is the season when the air grows crisp, the leaves fall, and the shadows grow long throughout the town. Night comes soon and stays longer. On the edges of town frightening things move freely, hastening the approach of travelers and skeptics. This week I’ll tell the tale of the witches’ Dark Hollow and the early usage of “jack o’ lanterns” in the Elm City.

On the border of East Haven and Fair Haven Heights exists a spot that was once known as the “Dark Hollow.” The spot is located on the old travelers’ road that in the 1660s would have been very isolated and surrounded by wilderness. In the mid-17th century anxiety was high throughout the Connecticut and New Haven Colonies concerning the matter of witches. During this time New England’s first witch trials took place in Hartford, and the New Haven Colony officially forbid witchcraft by law in 1655. Puritan life in the colonies was bleak and strict, and in the very small communities of East Haven and New Haven, residents were suspicious and fearful of outsiders. Behaviors that did not fit within the harsh structural norms of their daily lives were met with disdain.

At the time of the trials news spread and the edgy colonists worried about the existence of witches and liberated spectral beings in their communities. As the tale goes, on a moonlit night on the way from the village of East Haven to the banks of the Quinnipiac River, a traveler rode past the Dark Hollow where to his surprise he was accosted by the floating images of two women that carried on a private and intimate conversation while moving at the same pace of his horses. When he called for them to reveal themselves they disappeared. He stopped and looked for them only finding an empty riding hood resting in the middle of the path where they were last seen. Days later he claimed to see and hear the laughing women again moving quickly at night through his personal orchard, shaking and disrupting the trees. Once again they vanished suddenly into thin air.  No one fitting his descriptions was ever found, accused or put on trial.


Nearly 250 years later, in the early 1900s, the streets of New Haven were illuminated every night by gas lamps. New Haven was particularly advanced in the usage of gas lighting however as one traveled further away from downtown the gas lamps were less frequent and the streets became darker.

In 1908, with a degree of devilish glee it was reported that the early evenings were increasingly being filled with ghouls and goblins carried by young children throughout the Irish neighborhoods. Following an old world tradition of carving faces from old potatoes or turnips to both honor and scare away a legendary undead being known as “Stingy Jack”, young kids fought back the darkness of autumn by harvesting and carving pumpkins. In imitation of Stingy Jack’s own ill-fated lantern (that he was to carry for eternity for tricking the Devil) they carved faces, lit candles and placed them inside. However in contrast to today, they would actually use the “jack o’ lanterns,” carrying them around as personal lights to guide their paths through the cold and shadowy Elm City streets.

In the 1910s, the Irish and Scottish immigrant traditions of going door to door and asking for food on last day of October began to combine with the “jack o’ lantern” rituals and America’s growing commercialization of both pagan and religious holidays. By the 1920s “trick or treating” for mass produced candies and sweets, and the assorted costumes and decorations now commonly associated with Halloween began to take hold in New Haven and across the country.

Jason Bischoff-Wurstle
Director of Photo Archives, New Haven Museum

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