Calendar of Events
Current Marathon Events
- Sponsored Event
- Nov 18, 2024 - Dec 30, 2024 Key West
- Waterfront Winter Wonderland
- Website
- 21 Quay Rd Key West FL 33040
- Liz Love E-mail
- Enjoy Visits with Santa, live music performances, and festive celebrations throughout the season! Home to Key Wests only ice rink, we will also have thrilling carnival rides and fun for the whole family at Waterfront Winter Wonderland!
- Buy tickets!
- Sponsored Event
- Jan 25, 2025 - Jan 26, 2025 The Lower Keys
- Big Pine & Lower Keys Nautical Expo
- Website Lower Keys Chamber Grounds MM31
- 31020 Overseas Hwy Big Pine Key FL 33043
- View video
- The LKCC welcome you Saturday Jan 25 8am-4pm and Sunday Jan 26 8am-2pm to one of our biggest events with over 100 vendors. This event is fun for the whole family and includes an array of nautical pieces and much more that makes Florida Keys living great
- Sponsored Event
- Jan 18, 2025 - Jan 19, 2025 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- Buy tickets! Call now!
- Sponsored Event
- Mar 29, 2025 - Mar 30, 2025 Key West
- NAS Key West Southernmost Air Spectacular
- Website Boca Chica Field, Key West
- Naval Air Station Key West FL 33040
- NAS Key West E-mail
- View video
- The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
- Buy tickets!
- Sponsored Event
- Dec 01, 2024 - Dec 23, 2024 Key West
- Key West Holiday Fest 2024
- Website Key West
- The Key West Lodging Association 305-296-4959 E-mail
- Key West Holiday Fest 2024 offers a month of festive tropical fun! Enjoy lighted parades, inn tours, concerts, holiday shows, and the Waterfront Winter Wonderland with ice skating, rides, and more. Events run Nov. 27–Dec. 31.
- Buy tickets! Call now!
- Dec 14, 2024 Marathon Arts & Culture
- Boot Key Harbor Christmas Boat Parade
- Ilene Clark E-mail Website
- Everything from lighted and decorated dinghies to yachts are to cruise in the 28th annual Boot Key Harbor Christmas Boat Parade. The festive parade begins at dusk and meanders past popular Boot Key Harbor waterfront restaurants. Parade awards and a party are to take place after the parade at Dockside at Boot Key Harbor, 35 Sombrero Blvd. Call Ilene at 561-542-2727.
- Dec 14, 2024 Marathon Arts & Culture
- 7 Mile SantaCon
- Website
- The inaugural 7 Mile SantaCon celebrates the holiday season in Florida Keys style with drinks, poker, the historic Old 7 Mile Bridge, Pigeon Key, and raising money for scholarships. This holiday-themed poker run - for those age 21 and over - costs $50 to enter. Your poker run card includes 4 stops that you can make by either car or boat from 12 p.m. to 4 p.m., with 1 free drink at each, plus entry to the Pigeon Key Holiday Spectacular on the island of Pigeon Key (go by the Pigeon Key Polar Express train, or walk or bike across the Old 7 Mile Bridge). Dress up in your Santa/holiday best to win prizes for best and worst dressed, to be awarded on the island. The restaurant/bar stops are: Keys Fisheries, Lighthouse Kitchen & Bar, Lazy Days South and Sunset Grille & Raw Bar. Register online or at Marathon Chamber of Commerce, 12222 Overseas Hwy.
- Dec 14, 2024 Marathon Arts & Culture
- Grassy Flats Full Moon Party
- Website
- Grassy Flats Resort & Beach Club hosts a full moon celebration from 6 to 11 p.m., 58182 Overseas Hwy. Advance passes $25, with day of entry $35. Enjoy live music, food by Bongos, drink specials, fire breathers, a rousing Junkanoo parade and more.
- Dec 15, 2024 Marathon Arts & Culture
- Key Colony Beach Christmas Boat Parade
- Website
- Boats of all shapes and sizes, bedecked with lights and festive holiday decorations, are expected participate in the Key Colony Beach Christmas Boat Parade. The parade begins at dusk with some of the best viewing spots along the Sadowski Causeway.