Updated on September 13, 2018.

Fall is right around the corner, and the fall and winter seasons always bring about some of our favorite festivals and events in St. Augustine! Here in The Ancient City, we pride ourselves on providing fantastic experiences for anyone and everyone who visits and lives in the city. Whether you are interested in listening to live music, partaking in delicious food and wine, taking a look back in history, or creating magical holiday memories, St. Augustine has something for you. We’ve put together a comprehensive list of major events and festivals happening for the rest of the year to add to your calendar!

Sing Out Loud FestivalSing Out Loud Festival

When: Sept. 1-2, 7-9, 14-16, 20-23, 2018

Where: Various locations in St. Augustine

About: Due to its great success last year, the Sing Out Loud Festival returns! This festival’s mission is to highlight the talent of more than 200 local, regional, and national singers, songwriters, and musicians.  The Sing Out Loud Festival will take place over the course of three weekends at various venues throughout the city including the St. Augustine Amphitheatre, Colonial Oak Music Park, Planet Sarbez, Prohibition Kitchen, Limelight Theatre, and more!

SAiRASAiRA Food and Wine Festival

When: Oct. 14, 2018

Where: River House

About: The St. Augustine Independent Restaurant Association (SAiRA) presents the 9th Annual SAiRA Food & Wine Festival. Enjoy appetizers, main courses, salads, and desserts from local restaurants and sample more than 100 wines from different parts of the world, along with local craft beer and spirits from the St. Augustine Distillery. There will also be a silent auction featuring vintage wines, dining gift certificates, chef-prepared private dinners, and more. Tickets are $75, and proceeds will benefit the Boys & Girls Club of St. Augustine.

greek festival logo2018 Greek Festival

When: Oct. 12-14, 2018

Where: Francis Field

About: The annual Greek Festival is a much-anticipated event in the St. Augustine community. It’s a fun time to learn about Greek culture and enjoy Greek food and pastries, traditional Greek dancing and music, kids activities, and more! Admission is $5.00 for adults and free for those 14 and under with paying adult. Active-duty military and first-responders receive free admission.

Surf Illumination 2018

When: November 16, 2018

Where: Pier

About: Join the festivities at Pier Park as St. Augustine Beach opens the door to the holiday season and thousands of tourists. Surf Illumination is their community holiday celebration that includes food vendors, music, refreshments, arts & crafts, and the Mayor throwing the switch to light the Holiday Christmas Tree.

A wooden tiny house that is red and white.2018 Florida Tiny House Festival

When: Nov. 16-18, 2018

Where: St. Johns County Fairgrounds

About: The Florida Tiny House Festival is coming back for its second year! If you thought last year’s event was big, you haven’t seen anything yet! There will be a large assortment of tiny houses and micro homes, work shops, presentations,  vendors, entertainment, and children’s activities to enjoy.

  • Friday, November 16, 2018 — Free to Public — check out the tiny houses, visit with vendors & builders,  enjoy live music
  • Saturday, November 17, 2018 — Paid Admission to Ticket Holders Only — workshops, presentations, lectures, outdoor concert
  • Sunday, November 18, 2018 — Paid Admission to Ticket Holders Only — announcements, workshops, presentations, lectures, Tiny House Awards presentations, prize giveaways, closing announcements.

NOL_Plaza (002)Nights of Lights

When: Nov. 17, 2018 – Jan. 31, 2019

Where: Downtown St. Augustine

About: St. Augustine’s Nights of Lights is known as one of the top lighting displays in the world and runs from November 17, 2018, through January 31, 2019. Locals and visitors gather round each year to watch the Nation’s Oldest City light up with over 2.5 million lights. Whether you’re interested in taking a romantic carriage ride around the city, exploring the lit up cobblestone streets, or scoping out the best local eateries, there is something for everyone in the crowd. The lighting ceremony for the Nights of Lights 2018-19 season, otherwise known as Light-Up Night, is November 17, so start planning your trip now.

StAugustineArtCraftFestival2St. Augustine Art & Craft Festival

When: Nov. 24-25, 2018

Where: Francis Field

About: This year will be the 52nd year that the St. Augustine Art & Craft Festival will take place. This annual event is a beloved tradition during the holiday season here in The Ancient City. Thousands come from all over to view and buy paintings, pottery jewelry, sculpture, glassware, photography, and many other types of handmade items. Peruse the work of talented artists and makers while enjoying live music, a kids art zone, and a historic village featuring the Textile Arts Guild of St. Augustine.

Rails to Trails Festival

When: Dec. 1-2, 2018

Where: Armstrong Park

About: This year will be the 6th Annual SEA Rails to Trails Festival! This two-day festival celebrates the Gullah Geechee heritage. This festival features arts & crafts, Gullah and country cooking, a farmers market, biking and walking trails, ring shouters, live music, and more! Funds raised from this event will help SEA (Spuds/Elkton/Armstrong) Community Help Resource Center, Inc. develop a community center and programs to serve the needs of rural and at-risk children and families experiencing a crisis. Overnight camping is available for tents and vehicles.

146 Washington Street. Photo credit: Garden Club of St. Augustine

146 Washington Street. Photo credit: Garden Club of St. Augustine

Christmas Tour of Homes

When: Dec. 2, 2018

Where: Downtown St. Augustine

About: This longstanding tradition features homes in the downtown historic district of St. Augustine. Join the Garden Club of St. Augustine as they present the 49th Annual Tour of Homes. This year will be “Christmas in the Flagler Era” themed! It will feature 6 homes in the downtown historic area and a tea and boutique at the River House. Tickets are priced at $30 and will be available for purchase on Oct. 1, 2018. You must purchase tickets before the event. Don’t wait until the last minute – this event sells out quickly!

A graphic with writing Bed & Breakfast Holiday Tours

When: Dec. 8-9, 2018

Where: Downtown St. Augustine

About: Each year, the St. Augustine Historic Inns puts on a Bed & Breakfast Holiday Tour where each participating bed & breakfast is decorated according to that year’s theme. This year’s theme is “25 Years and 25 Inns. A Silver Jubilee Tour.” This is a self-guided walking tour where you can start at whichever inn you like and go in the order you wish. Each inn will feature delicious food, treats, and beverages from restaurants in the area.


Photo credit: St. Augustine Yacht Club

Holiday Regatta of Lights Boat Parade

When: 2018 Event TBA

Where: Downtown St. Augustine Bayfront

About: The St. Augustine Yacht Club presents the Holiday Regatta of Lights. Each year, visitors and locals alike line up along the bayfront just north of the Bridge of Lions to watch the sailboats, trawlers, shrimp boats, and other festively decorated vessels parade through the water. It’s always recommended to arrive early to get a good spot to view the parade.

beach blastoffBeach Blast-Off

When: Dec. 31, 2018 from 5-10 p.m.

Where: Pier

About: What better way to ring in the new year than by celebrating at the beach with friends, food, and fireworks? This great family-friendly New Years Eve event is a beloved annual tradition by all in St. Augustine.