Step into the shadows of St. Michaels, Maryland with a guided ghost walk that reveals spooky stories and historic secrets. Perfect for curious travelers seeking a unique nighttime adventure.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1.5–2 hours
Fitness Level
Minimal physical effort is required; suitable for most fitness levels including beginners and families.
Wildlife
History
St. Michaels played a significant role during the War of 1812 and has a rich maritime history contributing to many ghost legends.
Conservation
Efforts to preserve St. Michaels’ historic structures help maintain the town’s character and protect its cultural heritage for future generations.
Chesapeake Ghost Walks
Step into the shadows of St. Michaels, Maryland with a guided ghost walk that reveals spooky stories and historic secrets. Perfect for curious travelers seeking a unique nighttime adventure.
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.
Wear Comfortable Shoes
The ghost walk involves walking on historic cobblestones and uneven sidewalks, so sturdy footwear is recommended.
Bring a Flashlight
Although the route is guided, a personal flashlight helps navigate darker areas and enhances the spooky atmosphere.
Dress for the Weather
Evenings can get chilly or damp near the bay area, so layering with a light jacket is advised.
Stay Aware of Your Surroundings
The walk includes narrow streets and uneven terrain; watch your step to avoid tripping or slipping.
Comfortable Walking Shoes
Provides stability and comfort on uneven cobbled streets.
Flashlight or Headlamp
Helps navigate darker areas and enhances safety during evening walks.
Light Jacket or Sweater
Keeps you warm during cool autumn evenings.
fall
Insect Repellent
Protects against mosquitoes and other bugs near the water.
summer