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Key West Events

Event calendar courtesy of fla-keys.com - The Tourism & Development Council of the Florida Keys

Events in Key West for October, 2020

Year:  Month: 
October 03,  in Key West
NEW DATE: Key West Paddle Classic
Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.
Contact: Sue Cooper 305-304-4259
Email: [email protected]
October 16,  in Key West
Fantasy Fest 2020 Streaming Variety Show
Although the live event remains canceled, fans of Key West’s Fantasy Fest can enjoy a virtual, streaming event that showcases the masking and costuming festival’s creativity and spirit. A high-energy variety show incorporating comedy, dance, music by local and national talents, raffles, surprise cameo appearances and even quirky cocktail-making demonstrations is to stream from 7 to 9 p.m. The show is to feature performances by multifaceted entertainer and female impersonator Randy Roberts, who has appeared on NBC Television’s “America’s Got Talent”; noted cabaret singer Jennifer McClain; The Kinsey Sicks, a self-proclaimed “dragapella beautyshop quartet” whose career credits include an off-Broadway smash; rocker and Key West police officer Joe Tripp and many others.
October 20 to November 30,  in Key West
Second Annual Key West Tropical Forest & Botanical Garden’s ‘Scarecrows in the Forest’
Stroll through the Garden and view scarecrow entries from local artists, nonprofit groups, and individual residents. Scarecrow creators are encouraged to use natural or recycled materials. Cash prizes will be awarded with 'Best in Show' chosen by garden visitors. The Garden is located at 5210 College Road, on Stock Island.
October 22,  in Key West
Paint and Sip Evening with a Key West Artist
Enjoy a fundraising event for the Keys' Montessori School, featuring a local Key West artist Susan Beskowitz, Master of Fine Arts. From 6-8 p.m., at Stone Soup Gallery at 802 White St. Art supplies including an 11x14 canvas with acrylic paints, wine and appetizers are included in $50 pp cost.
October 23 to October 24,  in Key West
Big Bawdy Boo-lesque Show
The Bi Bawdy Boo-lesque Show runs for two evening performances featuring Amour along with a hit-list of favorite local performers, international burlesque superstars, amazing aerial acrobats, and all your favorite Frightening characters including vampires and vixens, monsters and more. Doors open 7:30 p.m., performance starts at 8 p.m., at Key West Theater, 512 Eaton St. Seating is to be socially distanced. Masks are to be worn inside the theater.
October 24,  in Key West
Fantasy Fest 2020 Streaming Event: Smallest Parade in the Universe
Capping an eight-week “Community Wins” fundraising campaign for local nonprofit organizations, the talent extravaganza is to include donation opportunities to help provide housing assistance to residents impacted by COVID-19. Fantasy Fest aficionados can enjoy a small-scale virtual version of Fantasy Fest’s traditional Duval Street parade of exotically decorated floats. Unique miniature floats are to take center stage in the 7-9 p.m. Float entries are to be “PG-13” rated, and may include lights and animated elements, but must not exceed a length, width or height of 18 inches. They are to “parade” down a replica of Duval Street while projections are flashed on the “street” to make them look like full-sized floats. At the parade’s conclusion, the floats are to be sold via an online auction. Proceeds are to benefit the Monroe Association for ReMARCable Citizens, a Florida Keys nonprofit that provides life services for adult developmentally and intellectually disabled residents.
October 28,  in Key West
An Evening with Paul Overstreet
Share an unforgettable evening with 2020 TRMA nominee ("Somewhere in the Caribbean") and iconic singer/songwriter, Paul Overstreet. You will laugh, you will cry, you'll have the time of your lives!! To be held at Key West Theater, 512 Eaton St. Doors open 7 p.m., show starts 8 p.m.