Greatest Hits Pool Party

Turn up the volume and join us for one of Fantasy Fest’s most unforgettable afternoons. The Greatest Hits Pool Party brings iconic music, poolside entertainment, and larger-than-life personalities together at Winslow’s Bungalows. Come dressed as your favorite music legend, take the stage for all-day karaoke, and dance between sets as our DJ keeps the party going. Stop by the merch booth for glitter, tutus, and Fantasy Fest favorites before competing for prizes for Best Dressed and Best Performance. Grab the mic, own the stage, and make this year’s Fantasy Fest your greatest performance yet. Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow’s Bungalows. Join us for an extended daily local favorite with half off select libations from 4 – 6 PM. Join us at Winslow's Bungalows for live music with Hub Chason. Known for his engaging acoustic performances and wide-ranging repertoire, Hub brings an easygoing island sound that's the perfect complement to an afternoon in Old Town. Start your Saturday with the sounds of reggae as Toko Irie performs live at The Bungalow Bar. Known for his smooth rhythms and uplifting island sound, Toko Irie brings an authentic reggae performance to the heart of Old Town, creating the perfect backdrop for a leisurely morning. Enjoy an afternoon of live piano music with Nina Newton at The Bungalow Bar at Winslow's Bungalows. Blending timeless melodies with contemporary favorites, Nina's performances create a relaxed backdrop for a leisurely afternoon in the heart of Old Town.