Have the Best Halloween Ever in Key West!

As October unfolds, Key West comes alive with a spirited energy that’s both thrilling and eerie. From Zombie Bike rides to haunted legends and trolley tours through historic graveyards, Key West offers a Halloween celebration unlike any other!

Key West has it all if you’re seeking spine-tingling tales, unique traditions, or simply a fun and memorable Halloween escape. So, prepare for a ghoulishly good time as we dive into the enchanting world of Halloween events and festivals in Key West.

Just moments away from your Key West house rental, you won’t want to miss these fun and spooky Halloween events in Key West!

Key West in October

October is a magical time to visit Key West. The island’s vibrant streets are filled with Halloween decorations, and locals and visitors often wear creative costumes. The Key West weather in October features balmy temperatures and a lively atmosphere, making it the perfect backdrop for Halloween festivities.

Pirates, witches, and zombies can be seen strolling along Duval Street or enjoying delicious drinks at Key West’s bars and cafes. The island’s laid-back vibe makes it easy to unwind on beautiful beaches or explore the historic district. Key West offers a unique blend of spooky and sunny experiences, making it an ideal destination for Halloween thrills and a relaxing island escape.

Pedal Til You Die – Zombie Bike

The annual “Pedal Til You Die” Zombie Bike Ride is a popular Halloween event in Key West, taking place on the Sunday preceding Fantasy Fest in late October. Participants, dressed in macabre and imaginative zombie attire, gather for a spine-chilling cycling journey through the streets of Key West. 

The ride starts just before sunset at the historic East Martello Tower, now the Key West Art & Historical Society. Riders of all ages and levels of cycling expertise are welcome, and the leisurely pace allows them to take in the captivating scenery and intricate details of fellow zombies’ costumes. Giving Key West locals and visitors the chance to showcase their creativity! 

creepy piano
Photo from Shutterstock

Haunted Key West

With its historic homes, forts, and cemeteries, it’s no wonder that Key West is often considered one of the most haunted cities in the United States. If you’re a fan of the supernatural or simply enjoy spine-tingling stories, visiting some of Key West’s haunted sites is a must.

Visit Robert the Doll at The East Martello Museum

The East Martello Museum in Key West houses the enigmatic and mysterious Robert the Doll. The 40-inch tall, dark-eyed, and peculiar doll was given to a young boy named Robert Eugene Otto, known as Gene. 

As Gene grew older, the doll’s influence became more unsettling, and some believed Robert was responsible. Despite his tumultuous life, Gene never parted with the doll, inherited the Otto family home, now known as the Artist House, and kept Robert locked away in the attic.

Visitors can view Robert in his glass case, donning a sailor suit, with his beady eyes and painted-on scowl. Legend has it that those who don’t seek Robert’s permission will face a curse of bad luck and misfortune. Over the years, countless letters have been sent to Robert, expressing the fear and respect he commands.

Plan Your Visit

Find the perfect place to call home for your Halloween adventure with Historic Hideaways! With our portfolio of carefully curated, historic homes, you’ll not only find a comfortable place to stay but also a piece of Key West’s rich history. View all of our rentals and start planning your stay today!

Captains Tony’s Saloon

Captain Tony’s Saloon, located on Greene Street, is a historic watering hole that has a rich history dating back to the time of Ernest Hemingway’s Sloppy Joe’s Bar. The dimly lit, weathered interior is a portal to another era, with the walls echoing past patrons’ laughter and conversations. 

The building, once the city’s morgue, is said to have a tree in the center where many souls met their end at the gallows. Those who believe in the supernatural claim that the souls of the hanged men still linger, casting an otherworldly presence over the establishment. One of the most famous spirits is a lady in blue, believed to be the spirit of a woman who tragically lost her life in a fire that consumed the building. 

Another eerie story involves Joe, a patron who died at the bar, whose ashes were scattered on the floor, and his spirit remains there to this day.

Key West cemetery

Key West Cemetery

Key West’s iconic cemetery in the Old Town district is a fascinating historical site with ornate gravestones, quirky epitaphs, and a rich history dating back to the mid-1800s. The cemetery offers more than a final resting place for the departed; it reflects the island’s eccentric charm.

Visitors can explore the cemetery’s winding pathways and lush greenery, encountering various tombstones that tell intriguing stories about the people who lived and died in Key West. One of the most famous graves is that of Elena Milagro Hoyos, a young woman whose tragic story has become the stuff of legend. 

Her restored mausoleum is now a popular stop for curious visitors. Key West Cemetery is also known for its sense of humor, with many gravestones featuring witty epitaphs and humorous messages reflecting the island’s laid-back spirit. The cemetery serves as a reminder of the diverse history and cultural influences that have shaped Key West over the centuries.

Blue Heaven Rooster Cemetery

The Blue Heaven Rooster Cemetery in Bahama Village is a charming and offbeat Key West experience. The cemetery pays tribute to the island’s colorful roosters and hens, who roam freely and serve as unofficial mascots. 

The cemetery features tiny headstones with amusing inscriptions dedicated to the departed roosters and hens, capturing the spirit of Key West. Blue Heaven, the famous restaurant adjacent to the cemetery, has embraced the quirkiness of the cemetery, often hosting live music in its outdoor seating area. 

Key West Ghost and Gravestone Trolley Tour

The Key West Ghost and Gravestone Trolley Tour is a thrilling adventure that takes visitors through the island’s haunted past. The tour begins with a dark trolley guided by knowledgeable guides dressed in period-appropriate attire. 

The tour takes passengers through Old Town Key West, where they hear ghostly tales of restless spirits, haunted mansions, and unsolved mysteries. The tour also includes visiting the infamous Key West Cemetery, where visitors can explore the island’s eclectic history. 

The tour is perfect for those who believe in the supernatural or enjoy an intriguing evening. However, its eerie nature may not be suitable for young children or those who are easily frightened.

Book Your Key West Vacation Rental with Historic Hideaways

Booking your Halloween in Key West with Historic Hideaways is the key to unlocking an authentic, historic, and unforgettable Key West experience! Whether you’re seeking a charming cottage, a luxurious beachfront villa, or a cozy Conch-style house, Historic Hideaways has the perfect home to match your vacation dreams.

Don’t wait until October to book one of these beautiful rentals in Key West. Make your reservation early for the best dates and rentals! Key West’s vibrant culture, stunning sunsets, and endless adventures await, book your stay today!