10 events are on across the Florida Keys this weekend, Oct 8–11: Original Works: Piano Concert by Nathan Kelly in Key West, Hurricane Cup to Benefit Guides Trust Foundation in Key West and Bike MS: Breakaway to the Keys 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 October 8, 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.
  • Key West Farmers Market — Thu, Oct 8, 1:00 PM · Key West · Festivals & Markets. Enjoy fresh local flavors at this vibrant open-air market.
  • Hurricane Cup to Benefit Guides Trust Foundation — Fri, Oct 9 – Sun, Oct 11, 7:00 PM · Key West · Races & Runs. A fishing tournament supporting hurricane relief efforts.
  • Original Works: Piano Concert by Nathan Kelly — Fri, Oct 9, 6:00 PM · Unnamed · Concerts & Live Music. An intimate concert featuring original piano compositions.
  • If The Shoe Fits: Key West National Finals — Sat, Oct 10, 8:00 PM · Festivals & Markets. Watch the national finals outside Bourbon Street Pub.
  • Southernmost Half Marathon and 10K (Run Conch Republic) — Sun, Oct 11 · Higgs Beach, 1000 Atlantic Blvd; 7:00 AM · Races & Runs. Half, 10K Confirmed 2026. No 5K. Half price rises after Sept 6.

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

Big Pine Key

  • Lower Keys Rotary Fall Festival/Haunted House — Fri, Oct 9 – Sun, Oct 11 · Lower Keys · Festivals & Markets. Celebrate community spirit with local food and fun events.
  • Open Air Market at Boondocks — Sat, Oct 10, 9:00 AM · Boondocks · Festivals & Markets. Experience local creativity and tropical charm every Saturday.

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

Key Largo

  • Bike MS: Breakaway to the Keys — Sat, Oct 10 – Sun, Oct 11 · Races & Runs. Participate in this cycling event benefiting MS support.

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

Marathon

  • Marathon Community Theatre Annual Fundraising Gala — Fri, Oct 9 – Sat, Oct 10 · 5101 Overseas Highway · Community. Join for a gala night to support local theatre.

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

Coming up in the Florida Keys later this month

  • Womankind Greene Street Fundraiser — Wed, Oct 14, 7:00 PM · Tattoos & Scars Saloon · Key West · Community. Help provide breast health screenings and life-saving diagnostic testing for women in the Florida Keys. Price: Varies with donation
  • Fantasy Fest — Fri, Oct 16 – Sun, Oct 25 · Key West · Key West · Festivals & Markets. Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. Price: Free
  • Fantasy Fest 2026 — Sun, Oct 18 · Key West · Festivals & Markets. Continuation of the festivities for Fantasy Fest 2026.
  • 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).
  • Reef Revival Inaugural Lionfish Derby- Captains Dinner — Thu, Oct 22, 5:30 PM · 260 Crane Blvd · Big Pine Key · Community. Participate in a fundraiser dedicated to protecting the marine environment by removing invasive lionfish from local reefs. Price: Varies with ticket
  • Reef Revival Inaugural Lionfish Derby- All Day Fishing — Fri, Oct 23 – Sat, Oct 24, 8:00 AM · 260 Crane Blvd · Big Pine Key · Community. Join the fishing derby that supports marine conservation and community outreach. Price: Varies with ticket
  • 2026 Relay For Life of the Florida Keys — Sat, Oct 24, 8:00 AM · Key West · Races & Runs. Participate in the 2026 Relay For Life to support cancer research.
  • Fantasy Fest 2026 — Sun, Oct 25 · Key West · Festivals & Markets. Finalize the exhilarating celebrations of Fantasy Fest 2026.
  • Reef Revival Inaugural Lionfish Derby- Weigh In & Prizes — Sun, Oct 25, 2:00 PM · 260 Crane Blvd · Big Pine Key · Community. Weigh in and win prizes at the Lionfish Derby, promoting marine conservation efforts. Price: Varies with ticket
  • Key West Halloween Pub Crawl — Thu, Oct 29 · Key West · Festivals & Markets. Join the spooky fun at the Key West Halloween Pub Crawl!

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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