September 1 - November 30
Key West Fishing Tournament
Contact Doris Harris 305-295-6601
Targeting multiple species, this annual challenge starts a season-long tournament that awards certificates for outstanding catches and prizes in a host of categories. This popular 8.5-month-long competition targets more than 40 species of fish.
September 5
Locals Day
Free admission to the Key West Aquarium, Key West Shipwreck Treasures Museum, Harry S. Truman Little White House and Conch Tour Train for families and individuals only. Must show proof of Monroe County (FL) residency.
September 7 – 12
Womenfest 2010
305-294-4603
For over twenty years, Key West has welcomed women from all over the globe to Womenfest Key West, the southernmost party for lesbians and their friends. Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests. Raucous clothing-optional pool parties, a sizzling dance club scene, sexy & competitive bull riding, and women-only water excursions promise to pique the interest of the more adventurous while film, live music, and comedy offer the opportunity to enjoy paradise at a slower pace.
September 17 - 20
Phil Peterson's 38th Annual Key West Poker Run
305-393-4827 |
October 1 - November 30
Key West Fishing Tournament
Contact Doris Harris - (305) 295-6601
Targeting multiple species, this annual challenge starts a season-long tournament that awards certificates for outstanding catches and prizes in a host of categories. This popular 8.5-month-long competition targets more than 40 species of fish.
October 3
Locals Day
Free admission to the Key West Aquarium, Key West Shipwreck Treasures Museum, Harry S. Truman Little White House and Conch Tour Train for families and individuals only. Must show proof of Monroe County (FL) residency.
October 22 - 23
Goombay Festival
Contact Ken Sullivan - (305) 896-5514.
1107 Whitehead Street, Key West, Florida 33040
Goombay is Key West's local favorite street festival. This will be the 30th anniversary celebration. Be a part of this local favorite cultural celebration. In the past Goombay has featured headline acts such as Sweet Emily, Geno D and the Spank Band and the Royal Bahamas Police Force Band. This year we will keep it local. Giving you the best of the best of All of South Florida. October 22nd is the VIP reception and block party in front of the Coral City Elks Lodge, 1107 Whitehead Street, our official headquarters. The Opening Ceremony will be held 6 PM at the main stage on Emma Street in front of the VFW on Emma Street; There will be local officials, gospel choirs and open microphone opportunities for local talent to perform on the stage. Friday and Saturday is the Street Fair where vendors from all over the world display their wares for you to purchase.
October 22 - 30
Fantasy Fest
Key West’s biggest party of the year with a week celebration filled with a variety of events.
October 22
Fantasy Fest ROYAL CORONATION BALL
6 pm (305) 296-6706
Meet Key West’s Royal Family and vote for the King and Queen of Fantasy Fest 2010; a benefit for AIDS Help, Inc.; Suggested donation; Location TBA.
October 26
Fantasy Fest REDDY ICE FANTASY FAÇADE ™ COMPETITION
Festively decorated homes and businesses compete for cold cash! To enter, call (305) 296-5334.
October 26
Fantasy Fest FREE OFFICIAL FANTASY FEST POSTER SIGNING PARTY
Crowne Plaza La Concha Hotel - 430 Duval St. - 5 pm - posters for sale.
Meet-n-greet the award-winning artists of this year's poster. Get up close and personal while having a lively libation or two.
October 26
Fantasy Fest
28th ANNUAL HEADDRESS BALL:
Diagnosis: Psychosis - An Assembly at the Asylum
Elaborate Headdress Contest, Show, and Party featuring live entertainment. Prizes for Best Headdress (costumes not judged) $1,000 first, $300 second, $200 third. Reserved Tables VIP for 4 - $320 or $270; standing / open seating in rear $30 (REDUCED from $40 with additional room and video screens). Location: Southernmost Hotel on the Beach, 508 South Street. Seating begins 7 pm, 8 pm Curtain. This event sells out, so please purchase tickets early by calling (305) 296-1520.
October 26
Fantasy Fest FINNEGAN'S WAKE GREEN PARTY
8 pm - 320 Grinnell St. - (305) 293-0222
Come celebrate the ultimate Irish party! Wear your green and receive NO COVER.
October 27
Fantasy Fest KEY PET MASQUERADE & PARADE
Casa Marina Resort - 1500 Reynolds St.
A magical carousel of frisky pets and playful owners delightfully disguised and ready to frolic for fame and fortune; Registration for competition is at 4:30 pm; FREE to watch; $25 to enter; benefits Lower Keys Friends of Animals.
October 28
Fantasy Fest SLOPPY JOE’S 27TH ANNUAL TOGA PARTY
“Still The Best Ancient Roman Party In Town!” To enter contest, contestants must be dressed in toga and are encouraged to dress in Fantasy Fest theme "Habitat for Insanity.” Three divisions: Groups/Couples $500 first place; Men’s $250 first place; and Women’s first place $250. Free to enter contest; registration at 8:00 pm and contest begins at 9:30 pm; Door charge; 201 Duval St.
October 28
Fantasy Fest Pretenders in Paradise
Pier House Resort & Caribbean Spa, beachside - (305) 296-4600
The legendary costume competition with $10,000 in cash and prizes! Combining extraordinary creative genius and performing energy, this year's event promises to be insanely entertaining.
October 28
MONSTER'S BALL
Green Parrot Bar - 601 Whitehead St. - (305) 294-6133
Sea serpents, mermaids and other bizarre creatures of the deep! What lurks below and who's dancing on the reef? Dive into this annual costume party and explore some surreal fantasies and some-too-real fantasies that should perhaps remain submerged!
October 29
FANTASY FEST STREET FAIR
12 pm - 10 pm
Duval Street's mile-long eater-tainment extravaganza features arts and crafts, food vendors, lively libations and costumed frivolity.
October 29
Fantasy Fest FAIRVILLA MEGASTORE MASQUERADE MARCH
Join the crowd as they parade through Old Town with music and noisemakers; thirst quenchers provided at selected guesthouses. Begins at the Key West Cemetery Frances Street entrance; revelers can join the mad march anywhere along the two routes; 5pm; All welcome; sponsored by Key West's costume headquarters - Fairvilla Megastore; FREE.
October 29
Fantasy Fest HEAVEN & HELL COSTUME CONTEST
www.southernmostresorts.com - Southernmost Hotel - 1319 Duval St. - FREE
All Angels and Demons are hereby summoned to enter Heaven or Hell’s Gates at Southernmost Hotel’s Annual Costume Contest Friday, October 30th from 4-6 pm, a pre-event to the half-way party of the Masquerade March. Wander through the pearly gates and step into the realms of Heaven or Hell at the Southernmost Hotel where all is relaxing and peaceful, or is it? See where your temptations take you.
October 29
Fantasy Fest RUM BARREL'S 4th ANNUAL PIRATE BASH
Dress and DRINK LIKE A PIRATE at the Rum Barrel! Key West’s resident pirate and rum experts - Pirate Soul Museum and Rum Barrel Restaurant & Bar - team up to throw the most outrageous Pirates Bash in the world! More than $1500 in cash prizes for the best pirate and wench costumes, great music on the rooftop stage, and awesome rum specials. More info (305) 292-7862.
October 30
Fantasy Fest DUVAL STREET PROMENADE
Noon - 10:30 pm; FREE
Sassy entertainers, enticing food and spirited libations tempt costumed merrymakers as they party from the Gulf to the Atlantic.
October 30
Fantasy Fest CAPTAIN MORGAN FANTASY FEST PARADE
Join 70,000 exuberant partygoers as this year's parade rolls down Duval Street. Featuring glittering floats, marching bands and dancing groups; it doesn't get any wilder than this! Parade route includes Whitehead, Front and Duval Streets; 7 pm.
October 31
FANTASY FEST SUNDAY BRUNCH AT THE HYATT
Served at SHOR American Seafood Grill at the Hyatt Key West Resort and Spa From 11 AM until 2 PM. 601 Front Street. Call (305) 809-4000 for reservations.
October 31
Children’s Day
A family event featuring food, games, arts and crafts and a costume contest for children. Bayview Park at Truman Ave. and Eisenhower Dr. (305) 292-8912.
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