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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.

Explore Resort Events for Exclusive Events, Lifelong Memories
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.

Visit Website Trivia Night at the Pub
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!

Visit Website Live Music at the Pub
Bingo at the Pub

Monday - Bingo at the Pub

Every Monday at 6pm

Test your luck and enjoy the thrill of Bingo! 

Every Monday at the Pub starting at 6pm

Visit Website Monday - Bingo at the Pub
Ice Cream Social

Ice Cream Social

Saturdays, 1:30 PM - 2:30 PM

Indulge your sweet tooth at our Ice Cream Social every Saturday.  It's a delightful occasion to share a few scoops with friends while supporting Care Camps. Because, after all, who can resist the allure of ice cream?

Visit Website Ice Cream Social
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

Visit Website Key West Pride