Ghostly Getaways: Halloween Road Trips on the East Coast

From Massachusetts to Florida, the Eastern Seaboard is stacked with spooky spots.

Greg Fitzgerald | 

Oct 11, 2024 | 4 min read

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Many of the oldest cities in the United States lie along the East Coast. Centuries of life — and death — have made for many eerie stories and purported hauntings. It's an excellent place, therefore, to celebrate Halloween.

From Salem, Massachusetts, where Halloween is the hometown industry, to 450-year-old Saint Augustine, Florida, the Eastern Seaboard is loaded with spooky sites.

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Eastern Massachusetts Has Lots of Spooky Spots

Eastern Massachusetts is home to many Colonial-era settlements, and with that long history comes many haunted places. A visit to Salem, which bills itself as hosting the largest celebration of Halloween in the world, can make for an iconic spooky-season trip.

The basis of Salem's macabre appeal are the Salem Witch Trials. Beginning in 1692, allegations of witchcraft rocked the town, and 20 people were put to death. Today, the city trades on this heritage with a monthlong celebration of Halloween known as Haunted Happenings. Haunted houses, séances, and ghost tours are all on the schedule, and many participants come in elaborate costumes.

From Salem, head two hours south to Plymouth, where the Mayflower landed in 1620 and the European settlement of Massachusetts began. With a history spanning four centuries, it's not surprising some hauntings have been reported. Burial Hill dates to the 17th century, and many Mayflower passengers rest there.

You can cap off your Massachusetts tour in Fall River, where in 1892, Lizzie Borden supposedly murdered her father and stepmother with a hatchet. As Borden was cleared at trial, the crime is officially unsolved.

The Borden house is now a bed and breakfast and museum, and adventurous travelers can stay the night in the room where Lizzie's stepmother died or go on a late-night ghost hunt.

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Savannah and St. Augustine Have Their Share of Scares

The history of Savannah, Georgia, is rife with war, disease, fire, and murder, and it was also a port of entry for the Atlantic slave trade. All of that dreadful history has allegedly made it one of the most haunted cities in the country.

Many operators offer ghost tours, which provide a sense of the city's haunted houses, hotels, and restaurants. Savannah also has beautiful Southern Gothic cemeteries, though haunted tours are banned.

The Jekyll Island Club, in the Golden Isles on Georgia's southern coastline, is about an hour and half south of Savannah. It was built as a luxurious hunting club for the wealthy elite. Today, it's rumored to be haunted by several former members.

To finish your trip south, hit St. Augustine, Florida, the oldest city in the United States. Settled by the Spanish in 1585, this city's long history leaves many haunting opportunities.

The Old Jail was the site of hangings and mysterious deaths under horrible conditions, making it an epicenter of paranormal activity. The St. Augustine Lighthouse is also a reported hot spot, said to be occupied by the daughters of the construction manager, who died in a tragic accident in 1873.

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Sleepy Hollow Leans Into Its Famous Fictional Tale

Washington Irving's "The Legend of Sleepy Hollow" is a short story about a German mercenary decapitated in the Revolutionary War who haunts the New York town of Sleepy Hollow.

Today, Sleepy Hollow is a suburb of New York City, but in the spirit of the Headless Horseman, it goes all-out in October. While the ghost tours and haunted mansions are all a fun way to get into the Halloween spirit, make sure to also visit Sunnyside, Irving's home in Tarrytown, New York, where you can get a sense of how he became the first internationally famous U.S. writer.

The end of October is also a lovely time to tour the Hudson Valley, as fall foliage erupts in color.

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Visit Edgar Allan Poe's Mid-Atlantic Haunts

Edgar Allan Poe was a famously macabre writer who wrote spine-chilling poems and stories. He spent his relatively short life — he died mysteriously at 40 — bouncing up and down the East Coast, from his birthplace in Boston to military service in South Carolina.

Richmond, Virginia, is a great place to begin a Halloween road trip. Poe grew up there, and the Poe Museum holds the world's largest collection of Poe materials. Those looking to learn about his life and work will be hard pressed to find a better starting point.

From Richmond, you can head north to Baltimore, where Poe died and is buried. The Edgar Allan Poe House and Museum preserves his home from 1833 to 1835, and his grave is at Westminster Burying Ground.

You can wrap up this Halloween road trip with a visit to Philadelphia, where the Edgar Allan Poe National Historic Site tells the story of the six years he spent there, during which he wrote "The Tell-Tale Heart."

Greg Fitzgerald

Greg Fitzgerald is a New Jersey-based writer, photographer, adventurer, historian, and Land Rover enthusiast. When he's not writing about travel or cars, he's probably getting away from it all in the wilderness.