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Exclusive Events, Lifelong Memories

At Sugarloaf Hotel, its all about creating memorable experiences. Our on-site events are designed to add excitement to your stay. Dive into the lively scene with live music, themed parties, and more. Discover what's happening during your visit and join the festivities for an unforgettable Florida Keys experience.  

From Seafood Festivals to Music Festivals to Pride Celebrations, there are great events and happening to explore around the lower keys.   Explore local events to help you plan your stay.

 Trivia Night at the Pub

Trivia Night at the Pub

Every Thursday, 6 PM - 8 PM

Get ready to put your knowledge to the test! Join us every Thursday at the Pub for Mania Pub Style Trivia from 6pm to 8pm. Think you know everything? Prove it! Win exciting prizes and enjoy a fun-filled evening of brain teasers and camaraderie.

Live Music at the Pub

Live Music at the Pub

Tuesdays and Saturdays

Experience some of the finest singers and songwriters from the Florida Keys. Our pub is open to everyone, and the music plays from 6pm to 9pm (unless otherwise noted through December).

Enjoy live music every Tuesday from 6pm to 9pm and weekends from 6:30pm to 9:30pm (unless otherwise marked). Get ready for a musical journey you won't want to miss!

Key West Pride

Key West Pride

June 5 - June 9, 2024

Events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The festival schedule typically includes pool parties at guesthouses and emporiums, drag shows by Key West's top performers, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively "Rainbow Roast."

Book your stay for Key West Pride

mini lobster diving

Mini Lobster Season

July 24 - 25, 2024

Mini Lobster Season is a highly anticipated event every year. If you have never experienced the frenzy you don't know what you are missing. This short sportsman season allows recreational users to catch lobsters prior to traps being deployed and commercial season beginning - also known to divers and snorkelers all over the world as "Mini Lobster Season"

Key West Offshore World Championship

Key West Offshore World Championship

November 3 - 10, 2024

Race World Offshore is excited to bring teams and fans to Key West for an amazing Offshore World Championship experience. RWO is the premier Offshore Racing Sanctioning body in the United States and our team is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event with the world's best offshore race teams in attendance!

Key West Half Marathon & Runfest

Key West Half Marathon & Runfest

January 17 - 19, 2025

Named as one of the United States' leading winter half marathons, Best Destination Half Marathons and Bucket List Best Half Marathons, is ranked among 13 must-do U.S. half-marathons by the courses include Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate.

Register for the Key West Half Marathon, 5k, 10k or the Big Pecker Challenge.

US Navy Blue Angels

Southernmost Air Spectacular

March 29 - 20, 2025

Naval Air Station Key West air show featuring the U.S. Navy Flight Demonstration Squadron the Blue Angels.

The show will feature the U.S. Navy Flight Demonstration Team, the Blue Angels, in addition to other talented civilian performers. The maneuvers that the Blue Angels perform are the same fundamental maneuvers that are employed in aerial combat.

Don't miss out on this incredible event with your family and friends. Enjoy spectacular flying, static displays, souvenirs, concessions and more.