St. Augustine Annual Festivals and Events

In early December, the St. Augustine Christmas Parade brings holiday cheer to the streets of downtown. Floats, marching bands and Santa Claus himself make an appearance in this beloved annual tradition. The parade winds through historic St. Augustine, spreading seasonal spirit to families and visitors alike. It’s a fun, festive way to kick off the holiday season in the nation’s oldest city and a long-standing tradition for local families.

For history enthusiasts, the Colonial Night Watch is a must-see for those looking for things to do in St. Augustine at night. Held in early December, this reenactment features actors dressed in colonial-era uniforms marching through the city streets. The procession culminates in a traditional weapons demonstration at Castillo de San Marcos, offering visitors a glimpse into 18th-century life. This event celebrates St. Augustine’s military history and adds an educational touch to the holiday season, attracting history buffs from far and wide.

Film buffs won’t want to miss the Saint Augustine Film Festival held in January. This event showcases independent films from around the world, including documentaries, shorts, and feature films. Screenings take place in various historic venues throughout St. Augustine, offering a unique cinematic experience in one of Florida’s most culturally rich cities. For those who love film, this festival provides an intimate setting to appreciate both the art of cinema and the beauty of St. Augustine’s venues.

For fitness enthusiasts, the Matanzas 5000 5K & Fun Run is a popular annual race held in January. Participants enjoy a scenic run through Downtown St. Augustine, taking in the historic landmarks along the way. The event is open to all ages and abilities, making it a fun and healthy way to start the new year. Whether you’re a seasoned runner or simply looking for a leisurely stroll, the race offers a beautiful setting for a workout.

Also hosted at Fort Mose, the Fort Mose Jazz & Blues Series is a celebration of African-American music and culture. Held in February, this series of concerts brings together top jazz and blues artists for performances at the historic fort. The event honors the rich cultural heritage of Fort Mose and its role in American history. This musical celebration is an uplifting way to connect with the spirit of Fort Mose while enjoying some of the best jazz and blues musicians in the country.

In March, the St. Augustine Celtic Music & Heritage Festival brings a touch of Ireland and Scotland to Florida’s oldest city. The festival features traditional Celtic music, Highland games, and Irish dancing. Attendees can enjoy authentic Celtic food and drink while learning about the Celtic heritage that has played a part in St. Augustine’s history. It’s a lively event that offers something for everyone, with competitions, performances, and plenty of family-friendly activities.

History comes alive with Searle’s Sack of St. Augustine, a reenactment of the 1668 pirate raid led by Robert Searle. This exciting event, held in March, includes battle reenactments, pirate encampments, and a thrilling mock invasion. Visitors can witness cannons firing and pirates storming the city in this dramatic reenactment of one of the most notorious events in St. Augustine’s past. It’s a fun and educational way to step back in time and experience the city’s pirate history.

A beloved tradition in St. Augustine, the Blessing of the Fleet takes place every spring. Local fishing boats, yachts, and other vessels gather in Matanzas Bay, where they are blessed by the local clergy in hopes of a safe and prosperous year on the water. This event is a nod to the city’s deep connection to the sea and maritime history. For spectators, it’s a beautiful and unique event to witness, steeped in tradition and community spirit.

Seafood lovers won’t want to miss the St. Augustine Lions Seafood Festival, held every March. This festival features fresh seafood from local vendors, arts and crafts, live music, and family-friendly activities. It’s a perfect event for those who want to enjoy the flavors of the sea while soaking in the coastal atmosphere of St. Augustine. The festival is also a major fundraiser for local charities, giving it an extra layer of community involvement.

Every April, Florida’s Birding & Photo Fest draws nature lovers and photographers from across the country. This event offers workshops, field trips, and presentations focused on birding and wildlife photography in the natural beauty of northeast Florida. The festival is perfect for both experienced photographers and beginners looking to hone their skills. It’s also a chance to experience the diverse wildlife that calls the region home, from birds to reptiles, in one of the best environments for nature photography.

Held over two weeks in June, the St. Augustine Music Festival is the largest free classical music festival in the United States. It features performances by world-class musicians in historic venues, such as the Cathedral Basilica of St. Augustine. The festival is a highlight of the summer cultural calendar and a must-attend for music lovers. Each concert brings a unique experience, blending stunning acoustics with the rich history of St. Augustine’s historic buildings.

For fans of water sports, the Florida Skimboarding Pro/Am Tournament is a summer highlight. Held in Vilano Beach in August, this tournament attracts top skimboarders from around the world. Spectators can watch the exciting competition and enjoy the lively beach atmosphere. It’s a fun and thrilling event that showcases the best in skimboarding while offering a relaxing day at the beach.

In September, St. Augustine’s Founder’s Day celebrates the city’s founding by Spanish explorer Pedro Menéndez de Avilés in 1565. The event includes a reenactment of the city’s founding, a Catholic Mass, and presentations on the city’s history. It’s a great way to learn more about St. Augustine’s Spanish heritage while taking part in a festive celebration. The reenactments are particularly well done, bringing history to life in a way that’s both educational and entertaining.

The St. Augustine Greek Festival brings Greek culture, food, and music to the city every October. Visitors can enjoy traditional Greek dishes like gyros and baklava, along with live music and folk dancing. The event also features a market with Greek crafts and gifts, making it a fun and flavorful way to experience a bit of Greece in St. Augustine. It’s a lively event that provides a cultural immersion into Greek traditions, from food to dance.

Car enthusiasts will enjoy the Ponte Vedra Auto Show, held just outside St. Augustine in October. This event showcases classic, exotic, and modern cars, with awards given to the best in show. It’s a must-attend event for automotive enthusiasts and families alike, blending a love for cars with a fun outdoor setting.

In September, St. Augustine celebrates “Locals Month,” where many businesses offer discounts and special events for local residents. It’s a great way for locals to explore the city’s attractions, restaurants, and shops for a special price. The event encourages community involvement and gives residents a chance to experience St. Augustine’s many offerings at a more relaxed pace.

The First Friday Art Walk is a monthly event where art galleries throughout St. Augustine open their doors for extended hours. Visitors can explore the local art scene, meet artists, and enjoy refreshments while strolling through the historic streets. The Art Walk is a wonderful way to experience the creative community in St. Augustine at night. With galleries offering new exhibits each month, this event is always fresh and exciting, making it a favorite for art lovers.

Held every Saturday at the St. Augustine Amphitheatre, the St. Augustine Farmers Market features fresh produce, handmade crafts, and live music. It’s a great spot to pick up local goods while enjoying the outdoors. The market is a favorite among locals and visitors alike, offering everything from organic fruits and vegetables to unique artisanal items. The vibrant atmosphere and variety of vendors make it a great place to spend a leisurely Saturday morning.

The Founder’s Day reenactment commemorates the establishment of St. Augustine by Spanish settlers in 1565. The event features a historical reenactment with actors portraying Spanish soldiers, settlers, and clergy, offering a glimpse into the city’s early days. It’s a vibrant celebration that highlights St. Augustine’s Spanish heritage.

In June, the Drake’s Raid reenactment commemorates Sir Francis Drake’s 1586 attack on St. Augustine. This lively event features a mock battle, complete with cannons and musket fire, as reenactors bring the 16th-century raid to life. It’s an action-packed way to engage with St. Augustine’s history, giving visitors a front-row seat to one of the most dramatic episodes in the city’s past.