Glebe House Museum to Debut Haunted Hollow Tours in Woodbury on October 24

As autumn settles across New England, golden leaves give way to bare branches, early sunsets cast long shadows over centuries-old stone walls, and crisp evening air brings an added sense of mystery to every walk outdoors. It is no surprise that historic cemetery tours grow especially popular around Halloween. Beyond seasonal scares, these experiences offer a compelling connection to local history, architecture, folklore, and the people whose lives helped shape their communities.

This year, the Glebe House Museum & Garden in Woodbury will introduce its new Haunted Hollow Tours on Saturday, Oct. 24, with a rain date of Oct. 25. Sponsored by Newtown Savings Bank, the event reimagines the museum’s classic cemetery tour with encounters involving the history, architecture, and memorable residents of Woodbury’s Hollow.

Participants will travel through another era while walking Hollow Road, Doolittle Hill, and Main Street. Along the way, they will meet the ghosts of former residents and enter Old South Cemetery to greet the spirits said to rest there. Six daylight tours will focus on the Hollow’s architecture, local history, and historic cemetery.

Six evening tours will offer a more unsettling experience, with spirits potentially appearing from the shadows of the ancient burial ground — listed among Connecticut’s most haunted sites.

With a spirit guide leading the way, attendees will visit the homes and final resting places of some of Woodbury’s most notable and notorious residents. The tours explore burial grounds more than 350 years old, where stories of those buried beneath visitors’ feet are brought to life for the occasion.

On the Glebe House grounds, guests can meet the Leatherman, the well-known wanderer who traveled throughout western Connecticut during the late 1800s and made numerous stops in Woodbury. Visitors may also encounter Dr. Samuel Orton, a physician who practiced medicine in the area more than 250 years ago and may be eager to diagnose modern ailments — and suggest a few leeches.

Tours depart from the museum grounds every 15 minutes, beginning at 4 p.m. Daylight tours run from 4 to 5:45 p.m., while evening tours run from 6 to 7:15 p.m. Evening tour tickets are available only to guests ages 13 and older, and organizers do not recommend the evening experience for children 12 and under.

The experience includes approximately 45 minutes of walking on sidewalks, uneven ground, and hills. Organizers recommend weather-appropriate attire, comfortable shoes, and a flashlight.

Guests may also sign up for tarot readings with Ana M. in the Glebe House Cottage. Ana M., who has more than 40 years of experience, will offer readings for tips, with 50 percent of proceeds benefiting the Glebe House Museum. Readings are valued at $30, and cash is preferred. Ticket holders will receive a reservation link, and advance sign-up is recommended.

Tickets are $15 for adults ages 13 and older, $10 for children ages 6–12, and free for children age 5 and under. Space is limited, and advance ticket purchases are encouraged. Last year’s event sold out.

For tickets and additional information, visit the Glebe House Museum & Garden website or contact the museum office at 203-263-2855 or office@glebehousemuseum.org.