Holidays

Creepy Road Trips

by Colleen Clark

St. Augustine to Key West, Florida

Dearly departed: The Sunshine State has a shadowy past lurking along its freeways. In St. Augustine, one of the country's oldest (and most haunted) cities, otherworldy screams and the sound of cannon fire torment tourists at the old Castillo de San Marcos. The spirit of a woman is said to swing lanterns at the Casablanca Inn, just as she did to warn off bootleggers whenever law enforcement stopped by during Prohibition. And if you leave before sunrise, you might spot Elizabeth, a teenage victim of the 1821 yellow fever epidemic, dancing alongside the city gates.

Spooky stops: Be on guard as you drive two hours south on I-95 to Orlando. Locals have seen a mysterious woman walking in her nightgown near Daytona's Orange Avenue Bridge. Even creepier is a stretch of I-4 at the St. John's River, which is thought to be built over a 19th-century graveyard. More than 2,000 accidents have occurred here since 1963, and phantom trucks, ghostly hitchhikers, and floating orbs have been sighted in the area. If you make it through the gantlet, laugh off your fears with the friendly ghouls in Disney's Haunted Mansion.

Final resting place: Continue south seven hours down US 1 to Key West, the bawdy haunt of long-dead buccaneers and rumrunners. Drink to their spirits at Captain Tony's Saloon, a former morgue and site of pirate lynchings. At the island's art museum, you can meet Robert. This possessed doll from the early 1900s would wake its young owner by throwing furniture. No surprise it inspired the movie Child's Play. Lay your head (if you dare) at the Artist House Bed & Breakfast, located in the same house Robert once terrorized.

See a map of this road trip itinerary

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Information may have changed since date of publication. Please confirm details with individual establishments before planning your trip.

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