12 events are on across the Florida Keys this weekend, Sep 17–20: Aaron Berg at Comedy Key West in Key West, Burgers & Buffet Tunes: A Tribute Show at Comedy Key West in Key West and MCT Children's Summer Theatre Presents Dare to Dream Jr. in Marathon. 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 17, 2026.

Key West

  • Aaron Berg at Comedy Key West — Wed, Sep 16 – Sat, Sep 19, 8:00 AM · Comedy Key West · Theater & Shows. New York comedian Aaron Berg brings four nights of fast-paced, unpredictable comedy. Price: Free
  • Burgers & Buffet Tunes: A Tribute Show at Comedy Key West — Thu, Sep 17, 12:30 PM · Comedy Key West · Theater & Shows. Dine with a legend at Burgers & Buffet Tunes, a tribute show at Comedy Key West.
  • Business After Hours — Thu, Sep 17, 5:30 PM · Flama Cabana · Festivals & Markets. An informal networking event held every month, perfect for making connections and exchanging ideas! Price: $10
  • Happy Hour with the Historian | Presidents in the Florida Keys: Power, Politics, and Retreat — Thu, Sep 17 · Key West Art & Historical Society · Community. Explore the surprising presidential history of the Florida Keys during a happy hour. Price: Free
  • Key West Farmers Market — Thu, Sep 17, 1:00 PM · Key West · Festivals & Markets. Discover vibrant local flavors, handmade treasures, and island charm at the Key West Farmers Market.
  • Prime of Life Yoga — Thu, Sep 17, 10:00 AM · Key West Tropical Forest & Botanical Garden · Community. Reconnect with your body, mind, and the natural beauty of Key West during Prime of Life Yoga.
  • Truman Waterfront Farmers Market — Thu, Sep 17, 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
  • Healthy Kids Running Series Fall 2026 - Key West, FL — Sun, Sep 20, 9:00 AM · Key West High School · Races & Runs. 4 Mile, 2 Mile, 1 Mile Who We Are: Healthy Kids Running Series is a five (5) week running program in the spring and fall for kids Pre-K through 8th grade. Each HKRS Series takes place once a week and offers… Price: $50

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

Marathon

  • Grassy Key Paddle Battle — Thu, Sep 17 – Mon, Sep 21 · Races & Runs. Make a splash in the Florida Keys with an unforgettable week of water sports, wellness, and island adventure at Grassy Flats Resort & Beach Club.
  • Herman Lucerne Memorial Backcountry Championship (2026) — Thu, Sep 17 – Sat, Sep 19 · Races & Runs. Experience one of the Florida Keys’ most distinctive fishing traditions when the Herman Lucerne Memorial Backcountry Championship returns to...
  • MCT Children's Summer Theatre Presents Dare to Dream Jr. — Thu, Sep 17, 3:00 PM · Marathon Community Theatre · Theater & Shows. Young performers from Marathon Community Theatre step into the spotlight for Disney’s Dare to Dream Jr.

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

Islamorada

  • Morada Way Third Thursday Art Walk — Thu, Sep 17, 6:00 PM · Morada Way · Festivals & Markets. Every third Thursday of the month, Morada Way comes alive with color, music, flavor, and island charm.

More: Islamorada festivals & markets · Islamorada: 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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