14 events are on across the Florida Keys this weekend, Oct 15–18: Burgers & Buffet Tunes: A Tribute Show at Comedy Key West in Key West, Hedwig and the Angry Inch at Waterfront Playhouse in Key West and Casting for Cats Backcountry Tournament in Islamorada. 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 October 15, 2026.

Key West

  • Cathy Rose: Object Lessons at JAG Gallery — Wed, Oct 7 – Sun, Nov 1 · JAG Gallery · Festivals & Markets. An opening reception kicks off this engaging exhibition.
  • Annual Music Festival — Thu, Oct 15 – Sat, Oct 17 · Downtown Park · Festivals & Markets. Join us for a weekend of music, food, and fun! Price: $50
  • Burgers & Buffet Tunes: A Tribute Show at Comedy Key West — Thu, Oct 15, 12:30 PM · Comedy Key West · Theater & Shows. Dine with a legend while enjoying a tribute show of music and laughter.
  • Hedwig and the Angry Inch at Waterfront Playhouse — Thu, Oct 15 – Fri, Oct 23 · Waterfront Playhouse · Theater & Shows. A bold and electrifying rock musical experience marking the season opener.
  • Key West Farmers Market — Thu, Oct 15, 1:00 PM · Festivals & Markets. Discover fresh local flavors and handmade treasures in a lively market setting.
  • Fantasy Fest — Fri, Oct 16 – Sun, Oct 25 · Key West · Festivals & Markets. Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. Price: Free
  • Fantasy Fest 2026 — Sun, Oct 18 · Festivals & Markets. Continuation of the festivities for Fantasy Fest 2026.

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

Islamorada

  • Morada Way Third Thursday Art Walk — Thu, Oct 15, 6:00 PM · Morada Way · Festivals & Markets. A vibrant evening of art, music, and community spirit every third Thursday.
  • Casting for Cats Backcountry Tournament — Fri, Oct 16 – Sat, Oct 17 · Races & Runs. Join the fishing tournament for a great cause in scenic Islamorada.
  • Ladies, Let's Go Fishing! Keys Saltwater Weekend — Fri, Oct 16 – Sun, Oct 18 · Festivals & Markets. A supportive environment for women to discover sportfishing skills.
  • Islamorada Witches Paddle & Halloween Costume Swap — Sat, Oct 17 · Community. Celebrate spooky season with paddling and fun costume swapping for families.

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

Key Largo

  • REEF Fest (2026) — Mon, Oct 12 – Sun, Oct 18 · Festivals & Markets. Dive into a weekend of underwater adventure, education, and conservation at REEF Fest. Price: Free
  • REEF Fest — Thu, Oct 15 – Sun, Oct 18 · Key Largo · Festivals & Markets. Dive into marine discovery and conservation at the annual REEF Fest.

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

Marathon

  • Witches in the Hammock — Sat, Oct 17 · Crane Point Museum & Nature Center · Community. A family-friendly celebration of the spooky season at Crane Point.

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

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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