October 2026
Redland International Orchid Festival
Oct 16–18, 2026 · Fri noon–5 PM · Sat–Sun 9 AM–5 PM
Fruit & Spice Park, 24801 SW 187th Ave, Homestead
Fantasy Fest
Oct 16–25, 2026 · Parade Sat Oct 24, 7 PM
Duval Street, Old Town Key West, Key West
Fall & Spooktacular Event
Sat Oct 17, 2026 · 5–9 PM
Losner Park, 104 N Krome Ave, Homestead
November 2026
Race World Offshore Key West World Championship
Nov 1–8, 2026 · Time TBA — check the organizer
Key West waters, Key West
Karaoke Night in the Park (monthly)
First Friday of each month · 6–10 PM
Losner Park, 104 N Krome Ave, Homestead
Key West Film Festival
Nov 18–22, 2026 · Time TBA — check the organizer
Key West, Key West
December 2026
Key Largo Boat Parade
Sat Dec 12, 2026 · 7:30 PM (boats line up 6:30 PM)
Blackwater Sound, Dusenbury Creek to Stillwright Point, Key Largo
New Year's Eve Red Shoe Drop
Dec 31, 2026 · Time TBA — check the organizer
Key West, Key West
January 2027
Rob's Redland Riot Road Rallye
Sat Jan 16, 2027 (third Saturday in January) · Starts 10 AM
Cauley Square, Homestead
Mile 0 Fest
Jan 26–30, 2027 · Time TBA — check the organizer
Key West, Key West
Homestead Championship Rodeo (78th)
Jan 29–31, 2027 · Fri gates 6 PM, show 8 PM · Sat–Sun gates noon, show 2 PM
"Doc" DeMilly Rodeo Arena, 1034 NE 8th St, Homestead
February 2027
Florida Keys Seafood Festival
Feb 13–14, 2027 · Sat 11 AM–8 PM · Sun 11 AM–5 PM
Truman Waterfront Park, Key West
March 2027
Original Marathon Seafood Festival
Mar 13–14, 2027 · Sat 10 AM–9 PM · Sun 11 AM–5 PM
Marathon Community Park, 200 36th St, Marathon
April 2027
Island Fest
Apr 10–11, 2027 · 10 AM–5 PM
Founders Park, MM 87 bayside, Islamorada
Dates TBC
Organizers haven't posted firm dates yet.
Birding Bonanza ranger bird walk (dry season)
TBCDates TBC (dry season, roughly Nov–Apr) · Time TBA — check the organizer
Guy Bradley Visitor Center, Everglades National Park, Flamingo
Key West Songwriters Festival
TBCDates TBC · Time TBA — check the organizer
Key West, Key West
Redland Summer Fruit Festival
TBCDates TBC (June 2027, per organizer listings) · Sat 10 AM–5 PM
Fruit & Spice Park, 24801 SW 187th Ave, Homestead
Lower Keys Underwater Music Festival
TBCDates TBC (usually July) · Time TBA — check the organizer
Looe Key Reef, ~6 mi off Big Pine Key (boat only), Big Pine Key
Dates checked against organizer and Florida Keys tourism pages on 2026-10-10; confirm before you go. The Keys trip planner reads this same list, so dates you see here show up there automatically.