The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by www.fla-keys.com.

Events in the Florida Keys for October, 2020
Year: Month:  
September 23 to October 08,  in Islamorada
Oktoberfest at Islamorada Brewery & Distillery
Spread out over two weeks and across the Islamorada Brewery’s taproom and beer garden for safe, laid back, themed fun! Enjoy specials on craft beer, cocktails and food, and compete for gift card prizes in the extended Oktobeergames.


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 07,  in Islamorada
Keys History & Discovery Center presents: Community Views, Early Upper Matecumbe Key
Part of the Keys History & Discovery Center’s fall season of programming, Community Views is a narrated pictorial presentation sharing photos of early days in Upper Keys communities. The Oct. 7 program starts at 6 p.m. and will explore early Upper Matecumbe Key. Advance registration required. $5 for non-members and free for members with member discount code. Offered via GoToWebinar.


October 10,  in Key Largo
Coral Restoration Foundation Event
Join the Coral Restoration Foundation and Amoray Dive Center to see how coral reefs are being revitalized and restored. Begin with a brief presentation and history of coral reef degradation and what the Coral Restoration Foundation and the Amoray Dive Center are doing to help. Following the morning presentation, there will be 2-tank dive trip: the first location is to the expansive, acre-sized coral nursery in the open ocean, home to over 400 coral "trees.” The second location can be to visit restored reefs, collect valuable data, assist with coral tree care or to plant corals! Both divers and snorkelers welcomed.


October 11 to October 14,  in Islamorada
50th Anniversary Islamorada All Tackle Bonefish and Permit Championship
Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants; events to be headquartered at Islamorada Fishing Club.
Contact: Kellie Trotta 561-346-3193
Email: [email protected]

October 15 to October 18,  in Key Largo
Key Largo Original Music Festival
An elite collection of musicians feature live knee-slapping and foot-tapping performances. The four-day festival features music to excite all ages and tastes, offering attendees an intimate look behind the original hits of songwriters/performers from Nashville, Georgia, Louisiana, Texas and Florida, all excelling in country, folk, pop, rock and blues.


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 21,  in Islamorada
Immerse Yourself: 15 Years of History of Diving Museum History
The History of Diving Museum is proud to celebrate 15 Years of History as a museum in the Florida Keys. Christopher S. Dutton, Esq., chair of the Museum’s Board of the Directors, has been affiliated with HDM since 2007. Chris will provide a timeline of how the museum came into existence and share many of the stories, told and untold, along the way. You won’t want to miss this virtual presentation and take a deep dive into what makes HDM such a great place!


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 25,  in Islamorada
'Ladies, Let’s Go Fishing!' Keys University
Aspiring anglers can learn, practice skills and go fishing at the award-winning weekend in the Sport Fishing Capital of the World. Hosted by the nonprofit Ladies Let’s Go Fishing Foundation, the “No-Yelling School of Fishing” offers classroom presentations, two networking events, hands-on skill practice and optional charter boat fishing. Classes will be held at the waterfront Elks Lodge in Tavernier. No equipment or experience is necessary. Pre-registration required; limited spots, COVID-19 safety protocols in place, as some events may be virtual.


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.




The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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