Ghosts & Gravestones of Key West
Take your seat on the Trolley of the Doomed and discover Key West’s darkest side—the side you can only see at night. We’ll travel along the dark, narrow streets of Old Town, where centuries old wooden buildings are said to be the home of raging occupants, souls who’ve never moved on. Be brave as we enter into an old Civil War barracks where soldiers died of yellow fever and where an eerie doll named Robert believed to be possessed, hopes to play with you. Learn the gruesome details of some of the island’s most tragic deaths, ghastly residents and more as your Ghost Host takes you on a tour of Key West you’ll not soon forget. The Travel Channel deemed Key West as one of America’s most haunted places; see for yourself during the Key West Halloween celebration. Tour departs from 501 Front Street—Conch Train depot, corner of Front and Duval Streets.
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Key West Fantasy Fest
Key West’s world famous Fantasy Fest takes place towards the end of October.
It’s an annual tradition that began in 1979 and has grown into a 10-day, raucous raising, party going, costume-wearing, body-painting extravaganza. With street parties, parades, food, drink and drag queen contests, the crowning of the Conch King and Queen and fundraisers to assist those with AIDS and HIV, Fantasy Fest rivals New Orleans’ Mardi Gras. Throw on a toga, a costume or just come as you are and join the nearly 100,000 people of all ages that flock to the island for their fill of laid-back, free-spirited, Halloween fun, Key West style! Enjoy the festivities that take place all throughout the island, including events and parties for the full 10 days.
Key West Halloween Half Marathon Series
Imagine hundreds of ghosts and goblins and maybe even a Spiderman or two running around Key West. Come check out a Halloween-themed running event where people dress in their favorite costumes. The annual half marathon and 5k are scheduled for the third weekend in October. There will also be parties held at local restaurants and bars in honor of this event. Visit halloweenhalfmarathon.com to register.