Big Pine Key, Florida, is a Florida Keys town on the Jupiter-to-Key West coast. This guide covers 12 upcoming events, kept current from official sources. Top picks: Open Air Market at Boondocks and Tunnel to Towers 5K Run & Walk - Big Pine Key. Nearest towns: Marathon (17 mi) and Key West (28 mi).

Last updated September 7, 2026. Events refresh daily; places are hand-picked and re-checked monthly.

Big Pine Key is Key deer country: the tiny endangered deer wander the National Key Deer Refuge and, often, the roads. Bahia Honda State Park next door has the best beach in the Keys and the snorkel boats to Looe Key reef.

For the live version of everything below, open the Big Pine Key page: things to do · events · where to eat.

What's on in Big Pine Key

The next 10 events on the Big Pine Key calendar (dates are America/New_York; confirm with the organizer before you go):

  • Open Air Market at Boondocks — Sat, Sep 12, 9:00 AM · Boondocks · Festivals & Markets. Bringing local creativity and island flavor to Mile Marker 27.5.
  • Tunnel to Towers 5K Run & Walk - Big Pine Key — Sat, Nov 21 · Big Pine Community Park, 31009 Atlantis Dr · Races & Runs. 5K Confirmed 2026. Packet pickup Nov 20 with Golden Knights parachute team.
  • Run With Deer 5K Run/Walk (11th annual) — Mon, Feb 15 · Big Pine Community Park, 31009 Atlantis Dr; 8:00 AM · Races & Runs. 5K run, 5K walk 2026 was Sat Feb 14. Benefits Florida Keys Wildlife Society.
  • Burgers & Buffet Tunes: A Tribute Show at Comedy Key West — Mon, Sep 7, 12:30 PM · Comedy Key West · Theater & Shows. Enjoy lunch while experiencing a unique tribute show.
  • Glow Hours at Hugh’s Views — Mon, Sep 7, 5:00 AM · Hugh’s View · Community. Experience a unique rooftop evening with stunning views.
  • Islander Resort Coastline Cleanup — Mon, Sep 7, 3:00 PM · Islander Resort · Community. Help clean up the beautiful shores of Islamorada.
  • Monday Night Jazz Jams — Mon, Sep 7, 8:30 AM · American Legion Post 168 · Concerts & Live Music. Kick off your week with smooth jazz tunes every Monday night.
  • Occupational Hazard: The First Coral Reefers — Mon, Sep 7, 2:00 PM · Key West Theater · Theater & Shows. A special two-show engagement highlighting the creative heart of Old Town.
  • Aqua Idol at the Legion — Tue, Sep 8 · American Legion · Theater & Shows. Cheer on local singers while supporting a great cause.
  • Arts & Drafts — Wed, Sep 9, 7:00 AM · The Retro Room · Festivals & Markets. Enjoy a relaxed, social art night with local creativity.

See the full list, refreshed daily: Big Pine Key.

Getting there and planning your day

Big Pine Key sits at 24.670, -81.354 in the Florida Keys. Parking rules, beach access and permits are on the Village of Islamorada site; the Florida Keys & Key West official tourism council calendar lists county-wide festivals; check the National Weather Service Key West forecast before a beach or boat day (summer storms build after 2 pm); snorkelers and anglers should read the NOAA tides: Vaca Key, Marathon; the nearest airport is Key West International Airport (EYW); the official Bahia Honda State Park page has hours and entry fees.

Nearby towns

Each has its own page in this guide:

Official sources and further reading

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

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