11 events are on across the Florida Keys this weekend, Oct 22–25: Hedwig and the Angry Inch at Waterfront Playhouse in Key West, Hedwig and the Angry Inch at Waterfront Playhouse in Key West and Hedwig and the Angry Inch at Waterfront Playhouse in Key West. 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 22, 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.
  • 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.
  • 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
  • Hedwig and the Angry Inch at Waterfront Playhouse — Sun, Oct 18 – Fri, Oct 23 · Waterfront Playhouse · Theater & Shows. Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience.
  • Hedwig and the Angry Inch at Waterfront Playhouse — Wed, Oct 21 – Fri, Oct 23 · Waterfront Playhouse · Theater & Shows. Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience presented...
  • Reef Revival Inaugural Lionfish Derby - Captains Dinner — Thu, Oct 22, 5:30 PM · Key West · Community. Join us for the Captains Dinner at the Reef Revival Inaugural Lionfish Derby. Price: Varies
  • Reef Revival Inaugural Lionfish Derby - All Day Fishing — Fri, Oct 23 · Key West · Community. Participate in all-day fishing for the Reef Revival Inaugural Lionfish Derby. Price: Varies
  • 2026 Relay For Life of the Florida Keys — Sat, Oct 24, 8:00 AM · Key West · Community. Participate in the Relay For Life to support cancer research and survivors.
  • Reef Revival Inaugural Lionfish Derby - Weigh In & Prizes — Sun, Oct 25, 2:00 PM · Key West · Community. Join us for the weigh-in and prizes for the Reef Revival Inaugural Lionfish Derby. Price: Varies

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

Islamorada

  • Florida Keys Farmers Market — Sun, Oct 25, 10:00 AM · Florida Keys Farmers Market · Festivals & Markets. Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada.

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

Big Pine Key

  • Sugarloaf XC — Sat, Oct 24, 8:30 AM · Sugarloaf Blvd · Races & Runs. 3K Sugarloaf Trail XC meet

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

Coming up in the Florida Keys later this month

  • Halloween Costume Contest/Party — Sat, Oct 31, 8:00 PM · Sloppy Joe's · Key West · Festivals & Markets. Join the Halloween festivities with a costume contest at Sloppy Joe's.
  • Zonta ABC (Awareness Breast Cancer) Run/Walk (34th annual) — Sat, Nov 7 · Higgs Beach, 1000 Atlantic Blvd; 10K 7:30 AM, 5K 8:00 AM · Key West · Races & Runs. 5K, 10K Confirmed 2026.
  • Tunnel to Towers 5K Run & Walk - Big Pine Key — Sat, Nov 21 · Big Pine Community Park, 31009 Atlantis Dr · Big Pine Key · Races & Runs. 5K Confirmed 2026. Packet pickup Nov 20 with Golden Knights parachute team.

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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