• Key West Artisan Market

    Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

    Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

    Free
  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Artisan Market

    Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

    Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

    Free
  • Sheriff’s Animal Farm Open House

    Monroe County Sheriff's Office Animal Farm 5501 College Rd, Key West, FL, United States

    Celebrate Christmas at the Monroe County Sheriff's Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities. Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!

    Gifts of fresh produce
  • Key West Songwriters Festival

    The Key West Songwriters Festival is the world’s largest of its kind and a career-launching event for country talent. It has helped kickstart the careers of stars like Kacey Musgraves, Florida Georgia Line, Jake Owen, and Maren Morris. Now in its 29th year, the festival attracts music lovers to Key West for five days and nights of live music and storytelling from both established and up-and-coming songwriters.

    Varies
  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • 34th Annual Schooner Wharf Minimal Regatta

    Schooner Wharf Bar 202 William Street, Key West, FL, United States

    Delicious food, island-style drinks, live music, and a FREE raffle set the stage for an unforgettable day on the Harborwalk. The real show? Homemade boats built from minimal materials (two sheets of plywood, a roll of duct tape, and some fasteners) racing — and often sinking — in spectacular fashion!

    Want to join the madness? Enter your vessel for a shot at awesome prizes and bragging rights. Whether you're building a boat or just here to soak up the fun, it's a day full of creativity, comedy, and community.

  • Key West Farmer’s Market

    Key West Farmer’s Market
    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Sunset Celebration at Mallory Square

    Mallory Square 420 Wall St, Key West, FL, United States

    Join locals and visitors each evening for Key West’s iconic Sunset Celebration — now with extra flair! From June 1 to June 20, enjoy nightly live music, street performers, artists, and food vendors, all leading up to the Summer Solstice on June 20.

    Celebrate summer’s arrival with island vibes, stunning sunsets, and unforgettable entertainment on the water. Don’t miss it!