Events & Festivals

January 2019

Jan. 5, 2019
Pole Vault in Paradise presents: Pole Vaulting Champions
Pole Vault in Paradise is a one-day competitive event open to pole vaulters of all ages and abilities. Spectators can watch as top athletes from around the United States join high school, college, and Masters pole vaulters. Admission is free, begins at 9 a.m. and continues throughout the day, at Truman Waterfront Park.

Jan. 10, 2019 – Jan. 13, 2019
37th Annual Key West Literary Seminar
888-293-9291
The 2019 topic is “Under the Influence.” Literary aficionados from around the world are to gather for readings, discussions and lectures led by some of contemporary literature’s most acclaimed writers. KWLS has assembled some of today’s most dazzling writers for a journey through literary archetypes—from Shakespeare and Homer to African folktales and early 20th-century novels and comic-book heroes—as we seek to understand the nature of literary influence.

Jan. 13, 2019 – Jan. 27, 2019
Key West Artisan Market
Art, food, wine, craft beer, shopping and entertainment. Free admission, from 10AM to 2PM at new location, Higgs Beach. January dates, 13 & 27. Bring your reusable bags.

Jan. 17, 2019 – Jan. 20, 2019
Key West Kingfish Mayhem
Jimmy Wickett 954-605-8284
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a 50-boat field.

Jan. 18, 2019 – Jan. 19, 2019
59th Annual Key West Home Tours
305-294-9501
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $45 each, seating is limited. Tickets without transportation are $35 in advance and $40 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Jan. 19, 2019 – Jan. 20, 2019
14th Annual Florida Keys Seafood Festival
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.

Jan. 20, 2019
21st Annual Key West Half Marathon & 5k Run
Barbara Wright 305-240-0727
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West’s balmy January climate. Named as one of the United States’ leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by Competitor.com.

Jan. 22, 2019 – Jan. 29, 2019
28th Annual Kelly McGillis Classic International Flag Football Championship
305-896-8678
Women and girls from around the world are to meet on the playing field for hard-fought sporting action. Each year, nearly 30 teams from across the United States, Mexico, Central America, Sweden and India participate.

Jan. 23, 2019 – Jan. 27, 2019
Key West Food & Wine Festival
800-474-4319
Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.

Jan. 25, 2019
Rams Head Productions presents: Air Supply at Sunset Green
The trademark sound of Russell Hitchcock’s soaring tenor voice and Graham Russell’s simple yet majestic songs have created a unique sound that helped Air Supply become a staple of early-’80s radio, producing seven straight Top Five singles. The albums “Lost in Love”, “The One That You Love”, “Now & Forever”, and “The Greatest Hits” sold in excess of 20 million copies during this era. In 2013, the duo was inducted into the Australian Recording Industry Association’s Hall of Fame. Air Supply celebrated their 40th anniversary in 2015 and continue to delight audiences all over the world. Doors open 6:30 p.m., show starts 8 p.m. Sunset Green Event Lawn is a multi-purpose event space located at 24 North Hotel.

 

February 2019

Jan. 29, 2019 – Feb. 2, 2019
Second Annual Mile 0 Fest Key West
Mile 0 Fest Key West is a new music festival considered a “must see” in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.

Feb. 1, 2019 – Feb. 2, 2019
Cuda Bowl
Loren Rea 305-360-6969
Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

Feb. 10, 2019 – Feb. 24, 2019
Key West Artisan Market
Browse among culinary, textile, jewelry, wood, artists & crafters, curiosities, live music, craft beer, wine and art and food concessions. From 10 a.m. to 2 p.m., at a NEW location this year, at Higgs Beach. Bring your own bags. A fantastic, family-friendly, free event. Dates: Feb. 10, 24.

Feb. 11, 2019
Key West Theater presents: Arrival From Sweden, The Music of ABBA
Witness the most authentic ABBA show ever, delivered in exact replicas of ABBA’s famous staging clothes exclusively approved by ABBA’s clothing designer. Arrival from Sweden performs together with some of the finest symphony orchestras in the world and also with ABBA original musicians. ARRIVAL from Sweden is the only ABBA tribute band in the world that has been given an unreleased ABBA song, “Just A Notion” directly from Björn Ulvaeus and Benny Andersson of ABBA. Doors open 7 p.m., show starts 8 p.m., Key West Theater, 512 Eaton St.

Feb. 14, 2019
Key West Theater presents: Los Lobos (Two Shows)
More than three decades have passed since Los Lobos released their debut album, Just Another Band from East L.A. Since then they’ve repeatedly disproven that title—Los Lobos isn’t “just another” anything, but rather a band that has consistently evolved artistically while never losing sight of their humble roots. Showtimes 6:30 and 9:30 p.m., Key West Theater, 512 Eaton St.

Feb. 15, 2019 – Feb. 16, 2019
59th Annual Key West Home Tours
305-294-9501
Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $35 in advance and $40 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.