CAROL TEDESCO/ One of the best places to see creative Halloween costumes — especially groups dressed alike — is at the Masquerade March on Friday, Oct. 25. The parade starts at the Frances Street entrance of the Key West Cemetery at 5 p.m., and breaks into two groups before meeting on Duval much later.

Friday, Oct. 18, 2013

• Goombay Festival

This family-friendly festival runs from noon to midnight on Friday and Saturday. The festival is held in Bahama Village on public streets closed to traffic. Vendors set up booths selling arts and crafts and delicious food along Petronia Street. The two days are punctuated by a variety of musical performances ranging from school-age children to trucked-in professionals.


Saturday, Oct. 19

• “Hero,” a burlesque musical

The promotional headline of this Waterfront Playhouse performance: “In the quest for fame and fortune, sometimes love gets in the way.” The production is billed as an Asian and fantasy-inspired tale set to tunes from the golden age of rock ‘n’ roll.  It runs for three nights, through Monday, Oct. 21. Curtain at 8 p.m.


Sunday, October 20

• Rhapsody Blue Party

Howard Livingston and the Mile Marker 24 Band play the third annual Blue Pool Party on Sunday, Oct. 20, from 1 to 4 p.m. at the Sheraton Key West. It features food, drinks and many giveaways and raffle items.

• The Heroes and Villains 5K sets off at 6 p.m. from the Reach Resort on Simonton Street. Runners and walkers are encouraged to exercise in costume. Register at


Monday, Oct. 21

• Womankind, a women’s health clinic in Key West, is fundraising with a bra auction. Organizers plan a bevy of beauties to model the one-of-a-kind brassieres that will be sold to the highest bidder. The gavel bangs at 6 p.m. at the Casa Marina Resort.


Tuesday, Oct. 22

• The 31st annual Headdress Ball is one of the original and true spectacles of Fantasy Fest. This year’s theme is “Bizzaro Key West” and the headdresses are typically gigantic and witty. The doors open at 7 p.m. (get to the Southernmost Hotel on the Beach early) and the show starts at 8 p.m.


Wednesday, Oct. 23

• Pet owners go all out when dressing their “babies” for the annual Pet Masquerade and Parade held at the Casa Marina Resort. The costumes go beyond dachshunds dressed as hot dogs and cats dressed as little old ladies. The duos perform together, sometimes to music, for prizes in a variety of categories. This is a fundraiser for an animal care nonprofit in the Lower Keys. Registration begins at 5 p.m. and the show starts at 5:30 p.m.

• The ‘Original Homemade Bikini Contest’

It’s been a few years since this event moved across town to The Sunset Pier, but its popularity is undiminished and the creativity is still roaring. We’ve seen everything from dollar bill bathing suits to ones made out of caution tape. The women compete for a big cash prize. The party starts at 9 p.m.

Thursday, Oct. 24

• Sloppy Joe’s Toga Party is another perennial favorite for Fantasy Fest goers.

To enter the contest, contestants must be dressed in toga … but any old sheet will not do. Participants are encouraged to glam it up and follow the Fantasy Fest theme. Prizes for individuals, small groups and big groups. Registration starts at 8 p.m. and the contest starts at 9:30 p.m.


Friday, October 25, 2013

• The Hair of the Hog Leather and Lace party is designed to dispel the evil hangover vapors with a “Bloody Mary Blow Out Breakfast” featuring breakfast burritos. There’s also an early morning costume contest for those wearing leather or lace. The party begins at 10 a.m. at Hog’s Breath Saloon and the contest starts at 11 a.m.

• This is the most democratic of all the Fantasy Fest events. Anyone who wants to be in the Masquerade March need only step off the sidewalk and join the throng of costumed paraders. The parade starts at the Key West Cemetery, splits into two groups and meets again on Duval Street. It starts at 5 p.m. and makes stops along the way at various guest houses for refreshment.


Saturday, Oct. 26

• Captain Morgan Fantasy Fest Parade attracts a cool 70,000 watchers as this very long procession of wacky floats, pretty costumes and great dancing group wends its ay down Whitehead Street to Front Street to Duval Street. The parade starts at 7 p.m. but doesn’t reach other portions of the route until later.


Sunday, Oct. 27

• Children’s Day is a family event featuring food, rides, games, arts and crafts and a costume contest for children located at Bayview Park. Festival goers pay with tickets redeemed at various booths operated by nonprofit organizations from noon to 5 p.m.


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