What To Do This Weekend in the Florida Keys: September 25-27, 2026

The last full weekend of September belongs to the water in the Florida Keys. The 26th annual Take Stock in Children Backcountry Challenge brings an around-the-clock fishing tournament to Key Largo, and the Conch Scramble turns Islamorada into a boat-based golf course with floating greens. Add a celebrated Friday-night show, two weekend markets, and nightly sunset celebrations, and there is no shortage of things to do this weekend in the Florida Keys. Here is a roundup of things happening across the Florida Keys September 25–27, 2026. Event details can change, so confirm with organizers before heading out.

Friday, September 25

Take Stock in Children Backcountry Challenge: The Tournament Kicks Off in Key Largo

The 26th annual Take Stock in Children Backcountry Challenge begins Friday, September 25, hosted by the Rotary Club of Key Largo. The event is based at Doc's Diner at 99696 Overseas Highway (Mile Marker 99.7) in Key Largo. Fishing starts after the Friday evening Captains and Anglers Meeting and continues around the clock until results are submitted Sunday afternoon.

It is a catch-and-release backcountry tournament targeting three species: snook, spotted sea trout, and redfish. Divisions cover adults, juniors, and children, and proceeds fund Take Stock in Children scholarships and mentoring programs for Florida students. Check the Rotary Club of Key Largo page for entry fees and the captains meeting time.

Conch Scramble Kickoff Party: Friday Night in Islamorada

The Conch Scramble charity golf tournament starts its weekend with a kickoff party on Friday, September 25, from 6:00 to 9:00 p.m. The 2026 Conch Scramble Kick-Off Party is scheduled for Friday, September 25, from 6–9 p.m. at Islander Resort in Islamorada. The event is open to the public, with dinner, an open bar and silent auction included with admission.

The Conch Scramble is a 501(c)(3) organization that makes grants to local Florida Keys nonprofits, and the party sets the tone for the tournament's signature mix of boating, golf, and costumes.

Hush Money: Friday Night Live in Key West

Friday night in Key West, Hush Money takes the stage at Hush Hush Theatre at 8:30 p.m. This new drag experience combines comedy, music, glamour and performances from Key West talent. The September 25 show is part of a series that continues October 9, 16 and 30.

From captains meetings to a glamorous encore, Friday sets up a weekend that is classic Keys: salt water by day, live entertainment by night.

Saturday, September 26

The Conch Scramble: Boat-Golf Tournament Day in Islamorada

Saturday is the main event in Islamorada. The Conch Scramble starts at 8:00 a.m., with foursomes traveling the bayside by boat to play out of floating greens with biodegradable golf balls. The awards ceremony follows at 3:30 to 4:30 p.m. The event raises money for local Keys nonprofits, and even the gallery gets into the spirit, with costumed players and island-style course rules.

Take Stock in Children Backcountry Challenge: A Full Day on the Flats

The backcountry challenge keeps fishing around the clock on Saturday, so anglers are out on the Key Largo flats from first light. The weekend also includes the event auction, a good reason for non-anglers to stop by Doc's Diner and support the scholarship cause. Spectators can watch weigh-in-style results and cheer on the boats coming in from the backcountry.

Boondocks Open-Air Market on Ramrod Key

Head to the Lower Keys on Saturday from 9:00 a.m. to 2:00 p.m. for the Boondocks Open-Air Market at Mile Marker 27.5 on Ramrod Key. The market sets up in the Boondocks Plaza parking lot, adjacent to Boondocks Grille & Draft House, with local crafts, tropical food, and island vendors. It is an easy stop along the Overseas Highway on the way to Key West.

Live Music in Key West

In Key West, the OurKeyWest events calendar lists Nick Norman: Live for Saturday, September 26. Confirm the venue and show time with the venue or on the Key West events calendar before heading out, then pair it with the nightly sunset celebration at Mallory Square.

Sunday, September 27

Take Stock in Children Backcountry Challenge: Final Day and Awards

The backcountry challenge wraps up Sunday, with results submitted in the afternoon and the dinner and awards banquet Sunday evening at Doc's Diner in Key Largo. It is a fitting finish to a weekend-long tournament that has raised scholarship money for Florida students for 26 years.

Florida Keys Farmers Market in Islamorada

The Florida Keys Farmers Market runs every Sunday from 10:00 a.m. to 3:00 p.m. at the Islamorada Gardens Plaza, 81001 Overseas Highway, Mile Marker 81. Pick up local produce, food, native plants, arts, and crafts, with live music and free parking. It is a relaxed, family-friendly way to spend a Sunday morning.

Lower Keys Fall Migration Mania: Birding at the Botanical Garden

The Lower Keys Fall Migration Mania takes place on Sunday, September 27, 2026, at the Key West Tropical Forest & Botanical Garden located at 5210 College Rd, Key West (Stock Island), FL 33040, with the Garden opening for early access/exploration.

A celebration of peak fall migration where nature lovers, birders, and butterfly enthusiasts can explore native habitats, observe seasonal migratory wildlife, and join optional guided tours led by local experts. It is a peaceful counterpoint to a fishing-heavy weekend, and a good chance to see songbirds, wading birds, and more.

General admission is typically $10 (free for Botanical Garden Society members).

Official event page: Key West Botanical Garden · Visit Florida Keys listing

All Weekend Long: Sunset Celebrations and Keys Essentials

Mallory Square Sunset Celebration in Key West

Every evening, the Mallory Square Sunset Celebration fills the waterfront at the foot of Duval Street in Key West with performers, street artists, craft vendors, and food. It starts about two hours before sunset and is free and open to the public, weather permitting.

Sunset and Tarpon at Robbie's of Islamorada

In Islamorada, Robbie's at Mile Marker 77.5 pairs sunset with tarpon feeding along the dock, and the neighboring Lorelei Cabana Bar hosts a nightly sunset celebration with live music. Sundance Watersports also runs sunset cruises from Robbie's on Florida Bay, one of the classic ways to close a Keys day.

Spiny Lobster Season Is Open

Regular spiny lobster season is open from August 6 through March 31. Visitors can enjoy locally caught lobster at Keys restaurants or, for those who are properly licensed and following applicable regulations, participate in recreational harvest. Check current FWC rules for size limits, bag limits, gear requirements and area restrictions before harvesting.

A Few Practical Notes

Late September in the Keys is still hot and humid, with the chance of passing afternoon showers. Pack sunscreen and water, and check the National Weather Service forecast plus your tour operator's status before a fishing, boating, or snorkeling trip. Many tournament and event details are subject to change, so call ahead or check the official event pages listed below.

Event schedules and details may change. Confirm directly with event organizers before visiting.