37th Annual Showcase of Key West Businesses Trade Show

October 15, 2026. Discover the vibrant business community that keeps Key West thriving at the 37th Annual Showcase of Key West Businesses Trade Show! Presented by the Greater Key West Chamber of Commerce, this long-running local tradition brings together a diverse array of businesses, organizations, and vendors from across the island for an afternoon and evening of connection, commerce, and community spirit.

Attendees can stroll among dozens of booths representing the very best of what Key West has to offer, from restaurants and retailers to service providers, nonprofits, and local makers. It is a wonderful opportunity to sample food and drinks, learn about local goods and services, enter giveaways, and meet the friendly faces behind the businesses that give the island its unique character.

More than just a trade show, this beloved event is a celebration of Key West's entrepreneurial heart and tight-knit community. For locals, it is a chance to reconnect with neighbors and discover new favorites; for visitors curious about authentic island culture and commerce, it offers a genuine peek behind the scenes of everyday Key West life.

Whether you are a Key West local, a business owner, or a visitor interested in experiencing the community beyond the typical tourist path, the Showcase of Key West Businesses is a fun, welcoming way to spend the day. Come sample, mingle, and celebrate the businesses that make the Southernmost City so special!