10 events are on across the Florida Keys this weekend, Sep 24–27: Take Stock In Children Backcountry Challenge in Big Pine Key, Key West Farmers Market in Key West and Paint Night at Divers Direct Key Largo in Key Largo. Below they are grouped by town with dates, venues and prices as published by the organizers; open any town for its full, daily-refreshed events list.

Last updated September 24, 2026.

Key West

  • Key West Farmers Market — Thu, Sep 24, 1:00 PM · Key West · Festivals & Markets. Discover fresh local flavors and handmade treasures at the Farmers Market.
  • Key West: Surface Interval Dive Social — Thu, Sep 24, 6:30 PM · Divers Direct · Community. Connect with fellow divers during this relaxed community gathering.
  • The Dive Community Hangout — Thu, Sep 24, 6:30 PM · Divers Direct · Community. Hang out with fellow members of the dive community, share stories, and connect with new buddies. Price: Free
  • Truman Waterfront Farmers Market — Thu, Sep 24, 2:00 PM · Truman Waterfront Park · Festivals & Markets. Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone! Price: Free
  • Monroe County Sheriff's Office Animal Farm Open House — Sun, Sep 27, 1:00 PM · Monroe County Sheriff's Office Animal Farm · Community. Come visit the animals at the farm including miniature horses, a steer, pigs, goats, bunnies, and more. Price: Free

More: Key West festivals & markets · Key West: where to eat

Big Pine Key

  • Take Stock In Children Backcountry Challenge — Fri, Sep 25 – Sun, Sep 27, 5:30 PM · Key Largo · Races & Runs. A family-oriented fishing tournament benefiting a good cause.
  • Open Air Market at Boondocks — Sat, Sep 26, 9:00 AM · Boondocks · Festivals & Markets. Explore local art, food, and crafts at Boondocks Market.
  • Lower Keys Fall Migration Mania Birding & Nature Adventure — Sun, Sep 27 · Key West Tropical Forest & Botanical Garden · Community. Celebrate fall migration with nature lovers and birders in Key West.

More: Big Pine Key festivals & markets · Big Pine Key: where to eat

Key Largo

  • Paint Night at Divers Direct Key Largo — Thu, Sep 24, 6:30 PM · Divers Direct · Festivals & Markets. Create ocean-inspired art during this free paint night event.

More: Key Largo festivals & markets · Key Largo: where to eat

Marathon

  • Kilts in the Keys — Sun, Sep 27, 5:00 PM · Marathon · Festivals & Markets. Celebrate Celtic culture at Kilts in the Keys with fun and festivities.

More: Marathon festivals & markets · Marathon: where to eat

Coming up in the Florida Keys later this month

  • Duval Mile — Sat, Oct 3 · Duval St. Pocket Park; 6:00 PM · Key West · Races & Runs. 1 mi On Southernmost Runners club calendar; RunSignup may still show 2025.
  • Old Highway 5K Run/Walk — Sat, Oct 3 · Coral Shores High School, Old Highway; 7:30 AM · Key Largo · Races & Runs. 5K Confirmed 2026. Flat, shaded out-and-back; shirts and medals to first 200.
  • Southernmost Half Marathon and 10K (Run Conch Republic) — Sun, Oct 11 · Higgs Beach, 1000 Atlantic Blvd; 7:00 AM · Key West · Races & Runs. Half, 10K Confirmed 2026. No 5K. Half price rises after Sept 6.
  • Fantasy Fest — Fri, Oct 16 – Sun, Oct 25 · Key West · Key West · Festivals & Markets. An electrifying 10-day costume and performance festival.
  • Fantasy Fest 5K Run/Walk — Mon, Oct 19 · Tiki House Key West, 203 Duval St; 6:00 PM · Key West · Races & Runs. 5K, 3/4 mi untimed Confirmed 2026. Evening costume run during Fantasy Fest (Oct 16-25).

Plan the weekend

Florida Keys & Key West official tourism council lists smaller community events we don't track; most arena and stadium tickets are on Ticketmaster; the National Weather Service Key West forecast decides beach plans; visitors fly into Key West International Airport (EYW). Dates and times are America/New_York and come straight from organizers' listings; we prune anything that disappears from its source.

Every town in the Florida Keys

Key Largo · Islamorada · Marathon · Big Pine Key · Key West

Official sources and further reading

We link to primary sources so you can verify hours, fees and dates:

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