Join the Princess Anne Ghost Walk for a chilling evening of haunted tales and paranormal exploration in Maryland’s historic town. Dare to explore sites like the old jail and Teackle Mansion after dark.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; involves moderate walking on uneven pavement and grassy areas.
Wildlife
History
Princess Anne was established in the late 18th century and holds deep colonial and Civil War history, making it prime ground for ghost stories.
Conservation
Local preservation efforts protect historic buildings and natural sites, ensuring minimal impact from walking tours on the community and environment.
Chesapeake Ghost Walks
Join the Princess Anne Ghost Walk for a chilling evening of haunted tales and paranormal exploration in Maryland’s historic town. Dare to explore sites like the old jail and Teackle Mansion after dark.
Chesapeake Ghost Walks is a Pocomoke City, Maryland–based operator offering guided ghost tours and a themed sunset cruise across the Eastern Shore. The company presents a range of experiences that explore local hauntings, maritime lore, and historic sites in Ocean City, Princess Anne, Cambridge, and Easton.
Highlights include the Ghosts of the Golden Hour Sunset Cruise in Ocean City, a Coastal Bays cruise with sunset views that pairs tales of pirates and shipwrecks with evening scenery. The Princess Anne Ghost Walk leads guests through nighttime sites such as the old jail and Teackle Mansion, concluding in a graveyard with a visit to a healing tree. Cambridge Ghost Walk follows Haunted High Street with 12 stops at historic homes and eerie local sites tied to soldiers and long‑time residents. The Easton Ghost Walk is a family‑friendly haunted walking tour featuring Foxley Hall, the Avalon Theater, and the old jail. In addition, Chesapeake Ghost Walks hosts a GUIDE MEETING for tour guides and staff to connect, exchange insights, and deepen knowledge of the region’s haunting history.
All offerings operate on a guided‑tour format and emphasize historical context alongside supernatural storytelling. Booking and schedule details vary by trip and location; visitors should review specific tour pages for dates, start locations, and age recommendations. Chesapeake Ghost Walks is featured on The Adventure Collective, where the itineraries and trip summaries are listed for travelers seeking haunted experiences on Maryland’s Eastern Shore. Schedules, pricing, and booking policies are available on each tour listing to help guests plan.
Based In
Pocomoke City, MD
Eastern Shore home base
Tours Offered
5
Guided walks and a sunset cruise
Seasonal Times
Sunset & Night
Evening-focused ghost experiences
Featured On
The Adventure Collective
Included in curated adventure lists
Book walking tours or the Ocean City Golden Hour sunset cruise today — check schedules and availability for each location.
Bring a flashlight
Carry a flashlight to navigate dimly lit areas safely during the nighttime tour.
Wear comfortable shoes
The walk covers uneven terrain and historic sites, so sturdy shoes will keep you comfortable.
Respect the sites
These historic locations are sensitive; avoid touching vandalism-prone areas or disturbing grounds.
Stay warm
Nights can get chilly, especially in spring and fall, so dress in layers to stay warm.
Flashlight or headlamp
Helps illuminate dark areas during the nighttime walk for safety.
Comfortable walking shoes
Necessary for traversing uneven historic grounds comfortably.
Camera or smartphone
Capture potential paranormal activity or atmospheric shots on the tour.
Layers or warm jacket
Keeps you comfortable during cool autumn and chilly spring or winter nights.
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