easy
1.5–2 hours
Participants should be comfortable walking for up to two hours at a leisurely pace on city sidewalks.
Experience the haunted history of Denton, Maryland on a private ghost walk filled with eerie tales and historic secrets. Join Chesapeake Ghost Walks for a night you won’t forget!
Starting at $20 | 1 Hour and 45 min | All Ages | Most Haunted Jail
1 Hours and 45 Min
Caroline County - 30 minutes from the Bay Bridge
Denton, the heart of Caroline County has many famous ghosts and one of the most actively haunted sites on the Eastern Shore – the Denton Jail, believed to be haunted by Wish Sheppard. They say Wish – an African American man of 19 – assaulted a white woman. He was condemned to hang. When he left his jail cell, he left a handprint on the wall. A print that would never go away, even after the Sheriff painted over it, plastered over it and even spread concrete over it. Wish wanted his presence known. So he’s been haunting the jail since the early 1900s. All of the staff, some of the inmates and even the Warden call the spirit that haunts the jail - "Shep."
There is continuous paranormal activity at the jail. And the Courthouse Green has been the site of two brutal lynchings (what lynching isn't brutal?"). Around the Courthouse green are five haunted properties in addition to the jail and the square.... making Denton the most actively haunted town on the Mid-Shore. In addition to walking the square, you'll walk through TWO graveyards - one so haunted that some locals won't walk on that side of the street at night. And you'll see the house of Dr. Knott and hear the stories of a ghost that haunts an old bank building.
PLEASE NOTE: WE DO NOT GO INSIDE THE PROPERTIES. This is a ghost walk where stories of hauntings and unexplained events are shared while standing outside the property.
MEETING PLACE: Meet on the corner of Market Street and Second Street on the Courthouse Green near the kiosk.
TIME & WEATHER: Ghost Walk begins on time. We walk in all kinds of weather except that which threatens public safety. Be sure to list your CELL PHONE number in the registration so we can contact you in the unlikely event the tour is cancelled.
TIPS / GRATUITIES: Cost of ticket does not include gratuity. Please give your guide a tip if you think she or he has done well and offered an informative and entertaining experience.
DRESS for the weather and be aware that each ghost walk takes at least an hour and covers between 1 and 1.5 miles.
CANCELLATIONS AND REFUNDS: Full refund will be given if cancellation is made 48 hours prior to the tour’s start. If cancellation is NOT made within 48 hours of the tour, no refunds will be given. However, all registrations are transferable, so feel free to allow a friend or family member to attend in your place. Just give them your order voucher.
The tour involves walking on uneven sidewalks and paths, so sturdy shoes are recommended.
A small flashlight can help illuminate dark spots along the walk and add to the spooky atmosphere.
Even nights in warmer seasons can get chilly, so layers are advisable to stay comfortable.
Arriving 10-15 minutes early ensures a smooth start and time to meet your guide and group.
Denton’s history dates back to the 18th century with tales of colonial-era hauntings and ghost sightings tied to its historic downtown buildings.
The town promotes preserving its historic sites and encourages respectful tourism to maintain the area's cultural and environmental integrity.
Supportive shoes are necessary for navigating city sidewalks and uneven surfaces during the walk.
Helpful for illuminating dim areas and enhancing the ghost-hunting experience after dark.
As temperatures drop in the evening, layering keeps you warm and comfortable.
fall specific
Protects against mosquitoes and other insects during warm summer evening tours.
summer specific