For most of the year, the tunnel that runs beneath Old New-Gate Prison & Copper Mine is a cold, wet, unlit hole in the ground — 52 degrees, dripping, and dark enough that the guides wear jackets even in summer. For a few weekends each October, it becomes something else entirely: a 100-yard loop of carved pumpkins, glowing underground.
The event is called "Light into the Dungeon," and its name is not decoration. In the late 18th century, the people confined at New-Gate were held in the abandoned copper mine itself, in total darkness, and the pumpkins are a deliberate inversion of that history. Visitors descend roughly 75 feet and walk the old workings past hundreds of professionally carved jack-o'-lanterns — listings for past seasons have put the count at 300, 350, and 400 — arranged along the passages where prisoners once sat in blackness.
The site's story starts long before the prison. The future prison began as a copper mine in 1705, while the land was still a British colony. The mine was chartered in 1707, the date the site still cites as its founding as America's first chartered copper mine. The ore played out; by 1773 deposits were harder to find and mining profits had disappeared.
That same year, the Connecticut General Assembly looked at the mine's labyrinth of caves and shafts and saw a prison. Colonial punishment was changing — whipping, ear-cropping, and branding were giving way to the idea of isolating offenders from society and reforming them — and a disused mine offered ready-made cells. The first prisoner arrived in 1773, a convicted burglar who lasted 18 days before escaping with help from a former flame. He was the first of many. New-Gate produced more escapees than copper ore; inmates slipped out of well shafts or past the meager guard force, sometimes with no explanation of how.
The prison held more than 100 people in its caverns at a time. During the American Revolution it became a political jail as well, holding British loyalists and prisoners of war, who were forced to climb down a narrow shaft into chambers one contemporary account described as reeking, filthy, and infested. The state kept adding fortifications, patrols, and exterior walls, and the reputation for an open-door policy faded, but the site never became what its planners hoped. It closed in 1827 and is now a National Historic Landmark operated as a history museum, with a visitor center, an outdoor prison yard, ruins above ground, and guided mine tours.
That is the setting for the pumpkin walk. The event runs on timed-entry blocks — in past seasons, Friday afternoons and evenings and 11 a.m. to 6 p.m. on Saturdays and Sundays through October — and tickets are limited and sell out early. Advance tickets have been required, with adult admission in the low $20s including fees and reduced pricing for children.
A few practical notes, drawn from the site's own guidance: the mine is consistently 52 degrees and wet, so dress warmer than the weather above ground suggests. The bats that hibernate in the mine from November through March are the reason the site closes for winter, and occasionally one wanders in during September or October to scout a hibernation spot. And yes, the site is often asked about ghosts. Its answer is that it chooses not to engage with the paranormal as part of regular interpretation, but visitors are welcome to make their own determination.
It is a strange thing to build a family outing around: a place designed to be as dark and miserable as colonial Connecticut could make it, now lit by several hundred grinning pumpkins and filled with children. But that is the appeal. New England has no shortage of pumpkin displays in October. It has exactly one inside a former copper mine that doubled as America's first state prison.