Monroe County Fairs & Festivals
6 events in Monroe County, Florida for 2026.
Towns in Monroe County
In 14 daysCraftFood FestivalArtisan
Key West Lobsterfest
Listen to incredible live music and savor delicious seafood such as fresh lobsters, jumbo shrimp, red skin potatoes, melted herb butter, freshly baked jalapeno corn bread, fresh corn on the cobb, and more.
Aug 5–9Key West
4.9(16)CraftFood FestivalArtisan
Key West Midsummer Artisan Market
A craft fair in Key West.
Sun, Aug 9Key West
4(1899)CraftFood FestivalArtisan
Fleming Island Fall Saturday Market
A craft fair in Fleming Island.
Sat, Oct 3Fleming Island
RecurringCulturalSeasonalFamily
Key West Fantasy Fest
A ten-day October costume celebration in the Florida Keys, famous for elaborate parades, street parties, masquerade balls, and the outrageous creativity of Duval Street.
Oct 16–25Key West
4.6(73)CraftFood FestivalArtisan
Fleming Island Autumn Saturday Market
A craft fair in Fleming Island.
Sat, Nov 7Fleming Island
4.5(1119)CraftFood FestivalSeasonal
Fleming Island Holiday Saturday Market
This market will feature over 30 vendors, music, bounce house for the kids, local food options, family fun activities, and more.
Sat, Dec 5Fleming Island