Experience live music, local art, and community in Old Kōloa Town at the 3rd Annual Southside Music & Arts Festival on Saturday, June 20, 2026, from 3 PM to 9 PM—free admission for all!
Presented by the Southside Arts Initiative, a nonprofit organization dedicated to supporting arts and culture on Kaua‘i, the festival brings together musicians, artists, local businesses, and the community for an unforgettable experience celebrating the creative spirit of the South Shore. This year’s festival will feature multiple event spaces, live performances, local vendors, art installations, and family-friendly activities throughout Koloa Town.
The afternoon begins with a festival pre-party in the Old Kōloa Town Courtyard, featuring select vendors and live music from local band, Underrated from 3 PM to 5 PM—creating the perfect atmosphere to kick off the celebration. As the evening continues, the festival experience moves across the street to the Big Grassy Lawn, where guests can enjoy additional local vendors, live entertainment, interactive performances, and large-scale art installations under the evening sky.
The lawn stage lineup includes:
• Garden Isle Jazz Trio | 5 PM–6 PM
• Pepper & the Scoville Scale | 6:30 PM–7:30 PM
• Desperado Orchestra | 8 PM–9 PM
Throughout the evening, festivalgoers can also enjoy special aerial performances between musical sets featuring Lyra, silks, and trapeze acts, bringing an added layer of artistry and spectacle to the event experience.
This year, proceeds from the festival will be donated to Little Miso Bookmobile, a fellow nonprofit organization dedicated to promoting early literacy skills for Kaua‘i keiki. With support from Old Kōloa Town, Fish Eye Kaua‘i, and Pho Kauai, the Southside Music & Arts Festival continues to create opportunities for connection, creativity, and community.
Event Details
🗓️ Saturday, June 20, 2026
🕒 3 PM – 9 PM (starting at the Courtyard @OldKoloa)
📍 Old Kōloa Town (at the end of the Tree Tunnel)
🎟️ FREE Admission
🎶 Live Music & Performances
🎨 Art + Local Vendors
👨👩👧👦 Family-Friendly – All Are Welcome
Don’t Miss It!
Bring your beach chair, gather your friends and family, and spend the evening celebrating art, music, and community in the heart of Old Kōloa Town.
Learn more at www.southsideartsinitiative.com
Follow on Instagram: @southsidemusicandart
