Sing Out Loud Festival 2027: St. Augustine Dates & Guide

Celebrating its 10th anniversary, the Sing Out Loud Festival 2026 returns to St. Augustine with its most ambitious format yet — over 100 free live performances spread across three full weekends in September (4–6, 11–13, and 18–20) at more than a dozen intimate venues throughout the city. Local and regional artists fill Colonial Oak Music Park, St. Augustine Distillery, and a rotating cast of historic venues with music ranging from folk and Americana to blues, indie, and everything in between. Three weekends of free live music in one of the most beautiful cities in Florida is an incredibly easy yes.

The 10th anniversary edition is the biggest Sing Out Loud yet. What started as a small showcase has grown into one of Northeast Florida’s most beloved cultural events — and the decentralized, multi-venue format means you can build your own experience, wandering from stage to stage through the cobblestone streets of the nation’s oldest city.

Event Schedule

Sing Out Loud 2026 runs across three consecutive weekends:

Weekend 1: September 4–6, 2026
Weekend 2: September 11–13, 2026
Weekend 3: September 18–20, 2026

Performances typically run Friday evening through Sunday afternoon. A full schedule of artists, times, and venues is released closer to the event on the official Sing Out Loud website. Each weekend stands on its own — you can attend one, two, or all three.

What’s Happening

• 100+ free performances across three weekends
• Local and regional artists spanning folk, Americana, blues, indie, and more
• Venues include Colonial Oak Music Park, St. Augustine Distillery, and historic indoor/outdoor spaces
• 10th anniversary programming and special performances
• Walkable format throughout the historic district

Admission & Access

Sing Out Loud is entirely free to attend. No tickets, no wristbands — just show up and enjoy the music. Some venues are seated, some are standing, some are outdoor parks. The walkable nature of St. Augustine’s historic district means you can move between stages easily without needing a car. Bring a blanket or low chair for outdoor lawn stages.

Planning Your Visit

St. Augustine’s historic district is compact and extremely walkable — most festival venues are within easy walking distance of each other. Parking is available in paid garages near the historic district; arriving early on weekend afternoons is recommended as spots fill quickly. St. Augustine hotels book up for Sing Out Loud weekends, especially the 10th anniversary — reserve accommodations well in advance. For more on what to see and do in one of Florida’s most charming cities, our St. Augustine Vacation Guide has everything you need.

Looking for more September events in Florida? Our full guide to the best Florida events in September 2026 has the complete lineup — and browse our Florida calendar of events for the full year.

Three full weekends of free live music in St. Augustine, a city that’s already one of the most beautiful in Florida — the Sing Out Loud Festival 2026 is one of the best reasons to visit this fall. Mark all three weekends and make a trip of it.