Calendar of Events

I.CARE’s Trash Derby, sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas, brings teams of environmentally-conscious debris collectors in divisions including dive charters, private boat owners and land lovers. After two days of trash collecting, there is a free festival Sunday at Founders Park, mile marker 87 bayside from noon to 6 p.m. The festival is open to the public. There is to be an awards ceremony to include cash and other special prizes. The festival features live music, food vendors, games and activities, raffles, a silent auction and exhibitors including local organizations helping to restore Keys coral reefs.

Experience the historical charm and vibrant culture of Old Key West through intricate wood carvings. This exhibition captures the essence of Key West’s bygone days, depicting its unique architecture, lush landscapes, and colorful local life. 533 Eaton St.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!

Vocal powerhouse Nate Smith has achieved remarkable success after just a few years on the country music scene with No. 1 hits including Whiskey on You, World on Fire and Bulletproof. Joining him for the amphitheater show taking place during the 2025 Key West Songwriters Festival is Chase Matthew, a rising star of the Nashville music scene. Doors open 6:30 pm.; show 8 p.m.

A guaranteed $18-thousand in cash awaits the top anglers who catch the largest bull and cow dolphin fish combined, while other prizes are awarded to anglers for 1st through 3rd place catches of the largest bull dolphin, largest cow dolphin, 3 largest dolphin combined, and the largest wahoo, tuna and tripletail. Tournament rules pick-up and weigh-ins at Two Conchs Bait & Tackle, 11499 Overseas Highway. Sunday evening awards banquet at Florida Keys Aquarium Encounters, 11587 Overseas Highway.

The story follows lovesick Ethan who plans to ask Alice’s parents for permission to marry her, but there’s one catch. Ethan and Alice broke up two years ago. Alice, reeling from having worked for a failed political candidate, is seeing someone else, but Ethan remains undaunted.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Cash prizes will be awarded for the heaviest mahi and to anglers who finish first through third place in this popular, family friendly annual fundraising tournament. There are four angler categories for prizes: professional, weekend warrior, lady, and junior angler. There is to be a captain’s meeting Friday night and one day of fishing on Saturday, followed by an awards banquet Saturday night. The “Fish for a Cause” event benefits Habitat for Humanity of the Middle Keys. Detailed information is available at www.mothersdaydolphintournament.com.

Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk. This is the season finale for Outdoor Movie Night

Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She performs at Key West Theater for one night. The show, originally scheduled for Jan. 9, was rescheduled due to the California fires. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.

Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.

Duane Betts, son of Dickey Betts of Allman Brothers Band fame, performs guitar-slinging, story-driven American rock and roll along with Palmetto Motel. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.

Intended for novice anglers and returning participants, this weekend is about learning and a non-intimidating, fun competition with the “Ladies Let’s Go Fishing” university organizers. Participants can join on a professional charter boat or fish on their own boat. This is a casual tournament with prizes for the heaviest offshore fish and longest inshore fish, drawings for prizes for those who caught fish, plus bonus drawings. The Friday kickoff takes place at The Tavernier Elks Club, mile maker 92 bayside; most Saturday and Sunday charters depart from Whale Harbor Marina, mile marker 83 oceanside.

Keys 100 is a 100-mile point-to-point running race from Key Largo to Key West. Both teams and individuals compete. There is also a 50-mile option from Marathon to Key West and a 50k individual race from Big Pine Key to Key West. All races finish at Higgs Beach on the Atlantic in Key West. 100-mile races start at Divers Direct in Key Largo, MM 99.8, and 50-mile races start at Marathon Garden Club.

The Golden Fly Tournament attracts top fly anglers and world class guides to test their abilities in Islamorada during the famed tarpon migration. The 3-day, invitation only tournament launches from the Lorelei Restaurant & Marina, 96 Madeira Rd.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.

Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.

Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.