September 2025 Events in St. Augustine: Festivals, Markets & Things to Do
- meganbkling
- Sep 2, 2025
- 3 min read
Looking for the best events in St. Augustine this September 2025? From live music and art festivals to historic commemorations and pet-friendly gatherings, the Nation’s Oldest City has something for everyone. Whether you’re a local or planning a visit, here’s your complete guide to the top things to do in St. Augustine in September.
When: Weekends, September 5–7, 12–14, 18–21, and select days through September 28
The Sing Out Loud Music Festival is St. Augustine’s largest free music celebration, drawing thousands each year. Enjoy performances from local, regional, and national acts across multiple venues. It’s one of the most anticipated St. Augustine festivals of 2025 and the perfect chance to discover new music in a vibrant setting.
When: September 5–6
Friday, Sept 5: 4 PM – 9 PM
Saturday, Sept 6: 12 PM – 9 PM
Celebrate Spanish Heritage Month in St. Augustine on Avilés Street, the oldest street in the United States. The Avilés Street Festival features live music, art displays, food, and cultural traditions. It’s a unique way to experience the city’s deep Spanish roots and one of the most colorful St. Augustine events in September 2025.
When: Saturday, September 6 | 10 AM – 5 PM
Step back in time at the Founder’s Day Commemoration. This annual event marks Pedro Menéndez’s 1565 landing and the founding of St. Augustine. Reenactments, ceremonies, and family-friendly activities take place at Mission Nombre de Dios and the Fountain of Youth Archaeological Park. It’s a must-see for history lovers visiting St. Augustine in September.
When: September 5–8
Watch talented artists set up their easels throughout the city during this plein air paint out in St. Augustine. From historic landmarks to waterfront vistas, painters capture the city’s beauty in real time. This is a unique cultural event that blends art with history and charm.
When: Select Wednesdays in September | 3 PM – 9 PM
Looking for a free midweek outing? Head to the St. Augustine Beach Pier for Music & Art by the Sea. This family-friendly event features a local art exhibition followed by live music with the ocean as your backdrop. Bring a chair or blanket and enjoy an evening of art, community, and beachside vibes.
When: Sunday, September 14 | 12 PM – 5 PMWhere: Lakeside Park, 2340 A1A S.
If you’re looking for pet-friendly events in St. Augustine, this one’s for you! Art & Bark in the Park combines live music, local vendors, food, and fun for both people and pets. It’s a tail-wagging good time and one of the more unique things to do in St. Augustine this September.
When: Tuesday, September 16 | 5 PM – 9 PMWhere: St. Augustine Amphitheatre, 1340C A1A S.
Spend an evening under the stars at the St. Augustine Night Market. Shop local crafts, enjoy food trucks, sip drinks from the full bar, and listen to live music in a lively community atmosphere. This event is a local favorite and a great way to experience the city after dark.
When: Saturday, September 27
Don’t miss this chance to visit Castillo de San Marcos National Monument for free on National Public Lands Day. Walk the historic stone fort, take in panoramic bayfront views, and explore over 300 years of history in St. Augustine—all at no cost.
For the most current information and additional events, please visit the the event links provided.
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