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Islamorada Events Calendar

The Official Florida Keys and Key West Web Site is your Premier Travel Guide to the Florida Keys: Key Largo, Islamorada, Marathon, Lower Keys, Key West. Accommodations, Real Estate, Diving & Snorkeling, Fishing & Boating, Museums & Tours, Restaurants & Bars, Theaters & Art Galleries, Events and more. Brought to you by the Monroe County Tourist Development Council.

Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel.
The first leg of the triple-crown Florida Keys Gold Cup Championship series is the only tournament in the series to offer a junior division for anglers age 16 and younger. Unlimited anglers are allowed per vessel.
Kids can frolic in a magical 30-ton snow mountain during the event at Founders Park, mile marker 87, and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a gift bazaar. Other activities include caroling and a holiday parade.
Kids can frolic in a magical 30-ton snow mountain during the event at Founders Park, mile marker 87, and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a gift bazaar. Other activities include caroling and a holiday parade.
Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events Saturday, Dec. 7. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Su
Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events Saturday, Dec. 7. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Su
Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid Florida Keys charities. This tournament has been held since 1964, one of the oldest sailfish events in the Keys.
Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid Florida Keys charities. This tournament has been held since 1964, one of the oldest sailfish events in the Keys.
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
For a casually elegant celebration, Cheeca Lodge & Spa, located at MM 82 oceanside, is planning live music and a midnight fireworks display over the Atlantic Ocean. Known for its renowned cuisine and beachside location, Cheeca is an ideal spot for revelers and romantics to ring in 2020. Call for more information about dining and reservations.
For a casually elegant celebration, Cheeca Lodge & Spa, located at MM 82 oceanside, is planning live music and a midnight fireworks display over the Atlantic Ocean. Known for its renowned cuisine and beachside location, Cheeca is an ideal spot for revelers and romantics to ring in 2020. Call for more information about dining and reservations.
Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
Revelers in the Upper Keys' Islamorada can ring in the new year with midnight fireworks on the beach at Morada Bay Beach Café at MM 81.6 bayside, who is to host a colorful large beach party with live music, beach barbecue, signature cocktails, performers and fireworks.
Created to raise money for Florida Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at Whale Harbor Marina to compete for top male, female and junior angler awards as well as top offshore, bay boat and fun fish categories.
Created to raise money for Florida Keys scholarships and domestic violence initiatives, this memorial tournament honors the late Holly Given, a Keys resident and avid angler. Participants are to gather at Whale Harbor Marina to compete for top male, female and junior angler awards as well as top offshore, bay boat and fun fish categories.
This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in one of the toughest and most exciting angling events of the year. For info visit floridakeysoutfitters.com and search "Sailfly entry" or visit the facebook.com/floridakeysoutfitters events tab.
This time of year the weather is ideal for a hot Atlantic sailfish bite. Enter for a chance to compete in one of the toughest and most exciting angling events of the year. For info visit floridakeysoutfitters.com and search "Sailfly entry" or visit the facebook.com/floridakeysoutfitters events tab.
Experience the fabulous restaurants of Islamorada, and don't miss the festival highlight at Postcard Inn Beach Resort & Marina scheduled for Saturday January 18, 2020. The Grand Tasting is a multi-sensory experience not to be missed. Area restaurants and wine experts will come together to present samples of their finest cuisine and world-class wines. Live music, celebrity chef appearances and cooking demos combine to serve up the recipe for a spectacular afternoon of tasting in the fabulous Flor
Experience the fabulous restaurants of Islamorada, and don't miss the festival highlight at Postcard Inn Beach Resort & Marina scheduled for Saturday January 18, 2020. The Grand Tasting is a multi-sensory experience not to be missed. Area restaurants and wine experts will come together to present samples of their finest cuisine and world-class wines. Live music, celebrity chef appearances and cooking demos combine to serve up the recipe for a spectacular afternoon of tasting in the fabulous Flor
Flavorful traditional bluegrass, old-time, "soulgrass" and Americana singing bands are to attract thousands of music lovers The three-day jam features satellite events at local spots and culminates in an all-day main event in a waterfront setting. Friday includes a weekend warmup with performing musicians, barbecue and a craft beer; Saturday features live music popups; Sunday at Founders Park, MM 87 bayside on Plantation Key, the weekend's main event is as much a craft beer festival as a musical
Flavorful traditional bluegrass, old-time, "soulgrass" and Americana singing bands are to attract thousands of music lovers The three-day jam features satellite events at local spots and culminates in an all-day main event in a waterfront setting. Friday includes a weekend warmup with performing musicians, barbecue and a craft beer; Saturday features live music popups; Sunday at Founders Park, MM 87 bayside on Plantation Key, the weekend's main event is as much a craft beer festival as a musical
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
Florida Keys Community Concert Band Presents its 2019-2020 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
Dubbed "almost too much fun for old guys to handle," the tournament is locally referred to as the Flutie, welcomes anglers age 50 and over. Proceeds benefit "Catch the Cure" for Cystic Fibrosis and the Monroe Association for ReMARCable Citizens, providing life services to Monroe County's adult intellectually disabled residents.
Dubbed "almost too much fun for old guys to handle," the tournament is locally referred to as the Flutie, welcomes anglers age 50 and over. Proceeds benefit "Catch the Cure" for Cystic Fibrosis and the Monroe Association for ReMARCable Citizens, providing life services to Monroe County's adult intellectually disabled residents.
Second in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.
Second in the Gold Cup series. Anglers put 20-pound line and light-tackle skills to the test during the two-day challenge against the high-flying acrobatic fish, known for tail-walking the waves. Only circle hooks can be used. "The Presidential" typically awards sophisticated sculpture trophies to top anglers who release the most sailfish.
Presented by the Islamorada Fishing Club, the event is the last leg this year of the three-pronged Florida Keys Gold Cup Championship series and typically draws a field of up to 30 boat teams of elite sport fishermen. Kickoff is 1/29 and fishing day is 1/30. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.
Presented by the Islamorada Fishing Club, the event is the last leg this year of the three-pronged Florida Keys Gold Cup Championship series and typically draws a field of up to 30 boat teams of elite sport fishermen. Kickoff is 1/29 and fishing day is 1/30. A total cash payout for a full field at the IFC Sailfish Tournament could reach $30,000.
Sponsored by the Florida Keys Fishing Guides Association, this all-release event offers team and individual awards to anglers for bonefish, redfish and snook. Anglers fish the shallows of the Florida Keys and the saltwater fringes of the Everglades. Social events are to be headquartered at the Lorelei Restaurant & Cabana Bar.
Sponsored by the Florida Keys Fishing Guides Association, this all-release event offers team and individual awards to anglers for bonefish, redfish and snook. Anglers fish the shallows of the Florida Keys and the saltwater fringes of the Everglades. Social events are to be headquartered at the Lorelei Restaurant & Cabana Bar.
This regional charity competition raises monies to spay and neuter feral cats in the Upper Keys. Trophies are awarded to first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others.
This regional charity competition raises monies to spay and neuter feral cats in the Upper Keys. Trophies are awarded to first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others.
In this light-tackle challenge, awards await the grand champion team (boat), first runner-up and second runner-up team, captain and mate. Other awards are presented for the high-point angler; outstanding catch; largest tuna, dolphin fish; kingfish; and hard luck. Proceeds benefit Keys charities.
In this light-tackle challenge, awards await the grand champion team (boat), first runner-up and second runner-up team, captain and mate. Other awards are presented for the high-point angler; outstanding catch; largest tuna, dolphin fish; kingfish; and hard luck. Proceeds benefit Keys charities.
Headquartered at the Lorelei Restaurant & Cabana Bar, this fun fishing event is only for actively employed bartenders and restaurant employees. Trophies are awarded to individual anglers as well as the bar a team represents, with the huge perpetual trophy going to the winners along with bragging rights for the year.
Headquartered at the Lorelei Restaurant & Cabana Bar, this fun fishing event is only for actively employed bartenders and restaurant employees. Trophies are awarded to individual anglers as well as the bar a team represents, with the huge perpetual trophy going to the winners along with bragging rights for the year.

Big Pine and the Lower Keys News

The Official Florida Keys and Key West Web Site is your Premier Travel Guide to the Florida Keys: Key Largo, Islamorada, Marathon, Lower Keys, Key West. Accommodations, Real Estate, Diving & Snorkeling, Fishing & Boating, Museums & Tours, Restaurants & Bars, Theaters & Art Galleries, Events and more. Brought to you by the Monroe County Tourist Development Council.

Key West Events Calendar

The Official Florida Keys and Key West Web Site is your Premier Travel Guide to the Florida Keys: Key Largo, Islamorada, Marathon, Lower Keys, Key West. Accommodations, Real Estate, Diving & Snorkeling, Fishing & Boating, Museums & Tours, Restaurants & Bars, Theaters & Art Galleries, Events and more. Brought to you by the Monroe County Tourist Development Council.

Enjoy a concert with both symphony and song: Barber's dreamy Knoxville: Summer of 1915 and Mahler's Symphony No. 4, both featuring Brandie Sutton (Bess from Porgy & Bess). Performance at 7:30 p.m., Tennessee Williams Theatre, 5901 College Rd.
Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center from 10-11 a.m., hosted by Fort Zachary Taylor State Park, a prime birdwatching location. Children will learn how migrating birds rely on the rich resources of the island chain during their seasonal journeys. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Dis
The focus is on fresh, locally sourced food offered by our growers and makers, from 10AM to 2PM. Stock your pantry and fridge with fresh produce, exotic fruits, artisan cheeses, local seafood, honey, pickles, nuts and so much more. Then share the bounty by bringing canned goods for donations to help a community kitchen fill their pantries to provide meals and snacks for our community's under-served children. Enjoy drinks, coffee, smoothies, natural juices and cut fruit, multiple food trucks and
The life of the tragically brilliant Zelda Fitzgerald is told by Zelda herself, and as it turns out, Mrs. F. Scott Fitzgerald has a lot to say on the subject of her husband, her work, and her life.  Performance at Key West Woman's Club, 319 Duval St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Showcasing films that exhibit excellence in storytelling, the festival's lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.
The international musical hit that changed the sound and the face of the Broadway musical. Tickets available online, showtimes TBA.
This exhibit of unusual and wonderful collections of knickknacks, curios, ornaments, trinkets, baubles, tchotchkes, artwork and objects collected by Key West/Florida Keys residents opens with a special reception from 6-7:30 p.m. in the Bumpus Gallery at the Custom House Museum, 281 Front St. Exhibit is to be on display through Jan. 5, 2020.
Key West is the largest historical district of wooden structures on the US Department of the Interior's National Register of Historic Places. The charm of Old Town can be attributed to the eclectic mix of over 3,000 wooden buildings constructed throughout the 19-Century; some of which were built in the Bahamas and brought to Key West. In her presentation, art historian Snow Philip will discuss the wide variety of styles and influences that led to Key West's unique architectural fusion. Snow live
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2019 Key West "Harbor Walk of Lights"with more lights and creative displays than last year, all continuing the "Maritime History of Key West" theme! The Key West "Harbor Walk of Lights" traditional main features will light up that night, including the Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree. Harbor Walk of Lights, lit nightly through New
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multi-division challenge that takes place Dec. 1 to July. 31, 2020. The tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for extended families and multigenerational groups who want to share the angling experience.
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. Bring your own bags! We invite you to "Rock the Red Ribbon Together" and wear a ribbon or pick up a free ribbon from volunteers of the Key West
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration begins October 1 online. This year the Coke Florida Caravan will be in Bayview Park to provide free photos with
Sutton Foster is an award-winning actor, singer and dancer who has performed in 11 Broadway shows - most recently the revival of Violet - and originated roles in the Broadway productions of The Drowsy Chaperone, Little Women, Young Frankenstein, Shrek The Musical, and her Tony Award-winning performances in Anything Goes and Thoroughly Moder. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd.
The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. Along with the awesome sights and excellent narration highlighting fun facts about the island, you'll also enjoy some complimentary tasty treats like cookies and hot cider. Give you and yours the gift of Key West this year! This tour has a duration of approximately 60 m
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
The Key West Triathlon expects up to 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances. Event highlights feature an Aquabike competition this year, along with a .76 km Atlantic Ocean swim from Higgs Beach, a 20km U.S. 1 cycling ride along South Roosevelt Boulevard and a 5km run along Smathers Beach.
Staged at the Hemingway Rum Company, 201 Simonton St., this evening begins at 5:30 p.m. with appetizers prepared by Iron Chefs and signature rum drinks, followed by a live art auction of pieces from the estate of Judge Tegan Slaton and his widow Rosemary Enright. Proceeds are to benefit the Wesley House. Admission is $20, and is applied toward any art purchase.
Join the Conch Tour Train for their annual holiday lights tour of the island. To get things started we will serve up some holiday cheer with cider and cookies. Then it is all aboard for an hour tour that takes you to all of the island's most elaborately decorated houses, buildings and neighborhoods and caroling. Departs from Key West High School, 2100 Flagler Ave., tour is approximately 60 minutes and departs from Mallory Square. Check website for dates and times.
Perpetual Groove continues to create a cultivated, unique experience for each live show. The Georgia jam veterans make a return to the live stage, equipped with a new album, revamped sound and lyrics, along with special guests, The Happy Dog Band. At Fort East Martello, 3501 S. Roosevelt Blvd. From 6-10 p.m. General Admission tickets $25, children 12 and under are free.
Stampeding elephants! Raging typhoons! Runaway trains! Unabashedly slapstick! Hold onto your seats for the original amazing race! Characters such as Phileas Fogg, Detective Fix, Passepartout, Sir Francis, Aouda and the British Council make for an evening of live entertainment. Showtimes 8 p.m.
Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet's photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys' community's homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Pa
Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Festivities are to begin at 6 p.m. with the children of Gerald Adams Elementary Steel Your Heart Band! Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.
Don your festive holiday running attire, affix your ruby-red nose, and join in the fun, starting and ending at the Southernmost Beach Café,1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, fun, prizes and a huge silent auction.
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The show will be st
From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.
As front man for the legendary rock band Poison, Bret Michaels has sold 25 million records and scored an amazing 15 chartbusting Top 40 singles including "Talk Dirty To Me," "Something To Believe In," "Nothing But A Good Time" and the timeless #1 smash "Every Rose Has Its Thorn." After more than 25 years in the business this award winning, multi platinum superstar's career continues to move at warp speed. Doors open 7 p.m., show starts 8 p.m.
From 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum. The immensely popular celebration will feature some of Key West's finest artisans, musicians and choirs, food and libations, free entrance to the museum and its two stories of exhibits, and a dazzling holiday light show of magical vector projections on the face of the Custom House. Browse hundreds of unique gift options while enjoying the music, food and libations on and around the island's architectur
This Olivier Award-winning comedy is a hilarious hybrid of Monty Python and Sherlock Holmes. Welcome to opening night of The Murder at Haversham Manor where things are quickly going from bad to utterly disastrous. With an unconscious leading lady, a corpse that can't play dead, and actors who trip over everything (including their lines). Showtimes 8 p.m., Tennessee Williams Theater, 5901 College Rd.
Imagine how it must've been to celebrate the holidays with the Truman's in the 1940s. An impeccably appointed tree decked with the finest ceramic and glass ornaments. The intoxicating aroma of cinnamon and spruce. Now you can travel back to a simpler time with this exclusive tour with some very special treats in store! Dates: Dec. 22, 23, 27 & 28; from 6:30 - 8:30 p.m.
1970s TV icon Lillian Baxter just had her show cancelled. What's a "everything's coming up roses" girl to do? Industrial musicals, game shows, sitcoms, and Broadway for a start! Lillian reminds us that what is lost can always be found. Performance 7 p.m. at Little Room Jazz Club, 821 Duval St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF's mission of "Celebrating and sustaining Key West's unique architect
Scorched-blues and Southern rock fans are going to love this show! Performances also from Georgia Satellites and Bishop Gun, of Natchez, Mississippi, rooted in the history and sounds of their home and the surrounding Delta, featuring a blend of rock and roll, soul and blues. Starts at 4 p.m. Key West Amphitheater, Truman Waterfront at 21 Quay Rd. Tickets available online.
Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The artists will be
Travel back to the 1960's for our 60th year anniversary themed NYE party. The fabulously dressed 21-plus crowd sets the scene. This is an exclusive event at the Garden at the Oldest House Museum, 322 Duval St. Limited Seating. The porch will also be open to watch the revelers promenade on Duval Street. Gate opens 6:00 pm; Dinner 8:15pm; Countdown at midnight. Tickets $225pp, available online.
The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.
The arrival of 2020 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.
For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2020. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.
Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
Enjoy a front-row seat for the famous "Lowering of the Wench" at Schooner Wharf Bar! This special adults-only event features complimentary beer, wine, champagne, well drinks, soda, and water and delicious hot and cold hors d' oeuvres! From 9:30 PM- 12:30 AM; tickets for purchase are limited so reserve early.
WWII is drawing to a close. In an abandoned boathouse, a Jewish immigrant woos a southern belle in this poignant romantic comedy. Can a new start really be found after so much loss? Performance 7 p.m., Back Room at the Key West Theater, 512 Eaton St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Presented by Key West Track and Field Club, Pole Vault in Paradise is an all-comers pole vault competition with events spread across four days. Youth, College, Elite and Masters divisions. Pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country.
The 2020 topic is "Reading Between the Lines, Sports & Literature." 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.
An acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. Sunset Green Event Lawn is a multipurpose event space located between 24 North Hotel and The Gates Hotel. Tickets can be purchased online or visiting the Key West Theater box office at 512 Eaton St.
Blake Pouliot, violinist, has quickly become one of Canada's most celebrated and promising young artists. He was the Grand Prize winner of the 2016 Orchestra Symphonique de Montréal Manulife Competition while featured on a number of television and radio broadcasts across North America including CBC Radio and NPR's Performance Today. All Impromptu Classical Concerts are at 4:00 PM at St. Paul's Episcopal Church, 401 Duval St. in Old Town.
Actor and comedian Sinbad has had audiences laughing for over three decades. His storytelling style of comedy is profound without being profane. Sinbad has recently appeared on Disney's "Planes," "Comedy Bang Bang," "The Eric Andre Show," FX Television series "It's Always Sunny in Philadelphia" and NBC's "Celebrity Apprentice". Sinbad produced and starred in his own WE TV's reality show, SINBAD: It's Just family." He has done six, one-hour comedy specials in his long comedy career, four on HBO a
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.c
Enjoy two powerful, strikingly beautiful and inspiring musical masterpieces: Bruckner's dynamic Symphony No. 6, and the U.S Premiere of Borenstein's glorious Concerto for Violin and Orchestra, featuring accomplished violinist Irmina Trynkos; along with the world premiere of Nardi's Upon An Ocean. Performance 7:30 p.m., Tennessee Williams Theatre, 5901 College Rd.
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.
Two legendary figures of the American Theatre, Tennessee Williams and actress Laurette Taylor, meet backstage before the opening night of The Glass Menagerie in Chicago to exchange best wishes. When an unopened bottle of scotch is discovered in her dressing room, sparks ignite as they are both challenged to face down a common demon. Showtimes 8 p.m.
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 $45 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.
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.
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.
Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens.
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.
Mile 0 Fest Key West is a "must see" music festival 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.
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.
Ambition and music collide when legendary blues singer, Ma Rainey, brings her band together for a recording session.  An American Masterpiece. 1984 NY Drama Critics' Circle Award winner. Performance 7 p.m., VFW Post 168, 803 Emma St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
In honor of the 250th anniversary of Beethoven's birth is this special presentation of his epic Symphony No. 9, with a full choir and the famous Ode to Joy finale. Also on the bill is Schumann's beloved Piano Concerto, featuring audience favorite, Svetlana Smolina on piano. Performance 6:30 p.m., Glynn R. Archer Center for the Performing Arts.
Canellakis-Brown Duo. Pianist and composer Michael Brown and cellist Nicholas Canellakis have been hailed as "a pair of adventurous young talents" by Time Out New York and lavishly praised by the New York Times as 'two outstanding musicians who are captivating audiences with innovative programs that combine masterpieces from the standard repertoire with original compositions and arrangements." The two highly acclaimed artists continue to pursue solo careers with performances in such venues as th
The time is 1959. The place is a seedy bar in Philadelphia. The audience is about to witness one of Billie Holiday's last performances, given four months before her death. More than a dozen musical numbers are interlaced with salty, often humorous reminiscences to project a riveting portrait of the lady and her music. Showtimes 7 p.m.