facebook pixel Skip to main content

Travel Worry Free! Select Trip Protection When Reserving Your Stay

Black Friday in May - 30% Flash Sale

  • 00 days
  • -
  • 00 hours
  • -
  • 00 minutes
  • -
  • 00 seconds


Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

How to Celebrate Halloween in Key West 2021

How to Celebrate Halloween in Key West 2021

October 15th, 2021 | Key West Events & Festivals

If you find yourself in Key West around Halloween time, you’ll see that it’s a rather busy time of year. Whether you’re stopping by via cruise ship or visiting the island especially for Fantasy Fest, we've got you covered on all things Halloween in Key West for 2021.

Although we strive to provide the most current information, events mentioned may be canceled without notice. We recommend checking the official individual websites for updates before visiting.

Do the Time Warp at the Rocky Horror Show

The 1975 Halloween classic cult musical The Rocky Horror Show returns to the Waterfront Playhouse at Mallory Square from Oct. 14 to Oct. 29.

Gather your Team for Halloween Trivia at Shanty Tiki

Head to Shanty Tiki for a special spooky Halloween trivia and a chance to be crowned “the wisest haunt of them all.” Come in costume to receive a free first round. Oct. 27, 8 - 10 p.m.

Hear Ghost Stories at Halloween Sip & Tales

Shanty Tiki continues the fun the following night with its Halloween edition of Sip & Tales. Hear Halloween tales about haunts and hauntings, win door prizes, enjoy spooky food specials, and indulge in a birthday cake for Robert the Doll’s 117th birthday. Oct. 28, 8 - 11 p.m.

Pay a Visit to Robert the Doll at the Fort East Martello Museum

Once belonging to a prominent Key West family in the early 20th century, legend has it the doll has supernatural abilities that allow it to move, change facial expressions, and giggle. Others claim the doll has moved objects around the room, disappeared, and caused "car accidents, broken bones, job loss, divorce and a cornucopia of other misfortunes.” Visit the Fort East Martello Museum on Halloween to see for yourself...if you dare.

See the Scarecrows in the Forest at Key West Tropical Forest & Botanical Garden

Enjoy a family-friendly Halloween at the Botanical Garden’s annual event featuring locally designed scarecrows by individuals, creative professionals, organizations, and businesses. Help choose the Best in Show winner. Kids visit free.

Step Back in Time on a Walking Ghost Tour

If you’re looking for a healthy dose of the Halloween scares, you’ve come to the right place. Key West is regarded as one of the most haunted places in America. A nocturnal stroll or pub crawl ghost tour will fill you in on the island’s spooky past and local haunts.

Hop on the Ghosts and Gravestones Trolley Tour

Take a ride to Key West’s dark side on the Trolley of the Doomed. The trolley will take you to the most famous ghostly sites on the island, with tales of the famous Captain Tony’s Saloon where not all the spirits are stored in bottles, the infamous Lady in Blue, and the haunted history of the Key West Shipwreck Treasure Museum.

Party at Fantasy Fest

Fantasy Fest takes costuming to another level, with countless opportunities for dressing up or down. Every day is Halloween during this 10-day festival (Oct. 22 - 31), with themed parties including the Toga Party at Sloppy Joe’s (who will also host a costume dance party on Halloween night), the Party in Plaid at Capt. Tony’s, the Red Party at Fogarty’s, and more. Be your best self and live out your costumed fantasy.

Allow Yourself a Few Illusions at Schooner Wharf’s Magic Show

Magician Frank Everhart performs a special up close and personal magic show on Halloween night at Schooner Wharf. Grab a drink, settle in, and suspend disbelief as miracles unfold in front of your eyes. The show starts at 9 p.m.


Check rates at The Gates Hotel – a Condè Nast award-winning hotel in Key West.

Share your opinion on this article