Oct. 1 - 5th Annual Sizzlin Soiree
Oct. 2 - A Starlight Stomp @ Wesley Wells Farms
Oct. 3 - Pink Up the Pace 2026
Oct. 3 - Nov. 1 - Sykes Family Farms Crop Maze
Oct. 3 - Taste of Latino Festival
Oct. 10 - Unity Pink Poker Run 2026
Oct. 10 - Donna 5K @ TPC Sawgrass
Oct. 10 - Mad Monster Halloween Market
Oct. 10 & 11 - Greek Festival 2026
Oct. 11 - Game On! St. Augustine Fall Triathlon
Oct. 11 - Betty Griffin Center Quarter Auction
Oct. 11 - St. Augustine Ballet: Dracula
Oct. 14 - 13th Annual Dark & Stormy Night
Oct. 17 - Shine-A-Light 5K for Epic Cure
Oct. 17 - Artistic Living Tour of Homes
Oct. 17 - Seafood & Jazz Festival
Oct. 23 - 25 - St. Benedict Blues Festival 2026
Oct. 23 & 24 - Creatures of the Night @ the Alligator Farm
Oct. 24 - 10th Annual Jail Break 5K
Oct. 24 - Annual Ancient City Kids Day
Oct. 24 - Halloween Trick-or-Treat Festival
Oct. 24 - Headless Bangers Costume Ball 2026
Oct. 25 - Walk With Us to Prevent Suicide
WEEKLY RECURRING EVENTS
Wednesday Pier Farmers Market
WHEN: Every Wednesday | 8:00 a.m. - 12:00 p.m.
WHERE: St. Johns County Ocean & Fishing Pier Park
The Wednesday Pier Farmers Market is a vibrant gathering where visitors can explore a wide array of fresh foods, hand-crafted items, local art and unique products. This beachfront market not only supports local merchants and the community by offering locally produced goods, but also provides a delightful experience of browsing through diverse vendors followed by a scenic stroll along St. Augustine Beach.
Amphitheater Farmers Market
WHEN: Every Saturday | 8:30 a.m. - 12:30 p.m.
WHERE: St. Augustine Amphitheatre
A lively and colorful event, presenting an array of fresh local produce, baked goods, seafood, flowers, distinctive arts and crafts, and more! It's a family-friendly event that combines the charm of organic offerings from local farmers with the added delight of live entertainment on certain occasions. Many vendors offer coffee and breakfast items to enjoy while you are browsing through the market.
Weekend Cannon Firing
WHEN: Occurs on most Saturdays and Sundays | 10:30 a.m., 11:30 a.m., 1:30 p.m., 2:30 p.m., 3:30 p.m. | Closed on Thanksgiving and Christmas.
WHERE: Castillo de San Marcos
Delve into history with the Weekend Cannon Firing event, where reenactors in period attire showcase weapons demonstrations and fire cannons, providing an immersive experience into the era of Spanish colonial settlers. You can watch the cannon firing up close by visiting the Castillo de San Marcos and head to the top before one of the above times, or just catch it from the bay front.
St. Augustine Art Association Monday Night Figure Drawing
WHEN: Every Monday | 6:00 p.m. to 9:00 p.m.
WHERE: St. Augustine Art Association's Art Gallery
The St. Augustine Art Association hosts a captivating Monday Night Figure Drawing event every week, offering artists a chance to hone their skills in capturing the human form. This non-instructional session invites artists of all levels to explore various mediums, with essential studio furnishings provided.
Improv Night at Colonial Oaks Music Park
WHEN: Every Wednesday | 7:30 p.m. to 9:00 p.m.
WHERE: The Colonial Oak Music Park
Improv Night at Colonial Oak Music Park is a unique, interactive comedy experience where the audience's suggestions drive the show, ensuring no two performances are alike. This family-friendly event features skilled comedians from First Coast Comedy, creating a spontaneous and enjoyable atmosphere in the heart of the downtown historic district.
Country Night at Colonial Oaks Music Park
WHEN: Every Thursday | 7:30 p.m. to 9:00 p.m.
WHERE: The Colonial Oak Music Park
The Colonial Oak Music Park hosts Country Night every Thursday featuring musical acts from the Northeast Florida region. County Night is curated in collaboration with Jacksonville's country music radio station 99.1 WQIK. During the free concerts, guests can watch hand-selected local and regional country music live in a rustic outdoor theater on St. George Street.
MONTHLY RECURRING EVENTS
First Friday Artwalk
WHEN: Every first Friday of the month | 5:00 p.m. to 9:00 p.m.
WHERE: Along King, St. George, and Aviles Streets. Galleries in the Uptown region and on Anastasia Island are also open for First Friday.
Sponsored by The St. Augustine Art Association, this event is a monthly celebration of art, where more than 25 galleries showcase an array of creative works from both local and national artists. This event, occurring on the first Friday of each month, provides a unique opportunity to explore diverse art forms in the historic downtown area and on Anastasia Island.
First Friday Garden Walk at Washington Oaks State Park & Gardens
WHEN: Every first Friday of the month | 10:00 a.m. to 11:00 a.m.
WHERE: Washington Oaks State Park & Gardens
Led by park rangers, this event is a 45-minute exploration showcasing the park's historical significance and diverse garden landscapes. This monthly event offers a unique opportunity to discover the park's 425 acres, which include rare coquina rock formations, tidal marshes, and historic formal gardens.
Sundays at Stetson's
WHEN: One Sunday a Month | Music Starts at 2:00 p.m. to 4:00 p.m.
WHERE: Beluthahatchee Park
A cherished monthly concert series held at Beluthahatchee Park, the former residence of writer and conservationist Stetson Kennedy. Each event, typically on the second Sunday of the month, features a different folk musician or group, celebrating the legacy and values of Kennedy, with free admission and an option for donations.
West King Wednesdays
WHEN: Every third Wednesday of the month from February through December | 5:00 p.m. to 8:00 p.m.
WHERE: West King District
West King Wednesdays is a monthly celebration in St. Augustine, showcasing a variety of pop-up markets, live music, local artists, and unique culinary offerings. This event brings together the community and visitors for an evening of culture and fun.
Boozin' on the Boulevard
WHEN: Every Thursday from 5:00 to 8:00 p.m. Note: Dates and times could be adjusted based on the number of sign-ups.
WHERE: Starts at Kaiser's Deli & Market at 4 White Street East, St. Augustine, Florida 32080.
ADMISSION: Food and drink prices vary at each establishment. Transportation is provided by Old Town Connect once a drink is purchased at Kaiser's Deli or Sogno Restaurant.
The bar crawl starts at Kaiser's Deli & Market and Sogno Restaurant from 5:00 to 6:00 p.m., moving on to Blackfly and Odd Birds Cocktail Lounge and Kitchen from 6:00 to 7:00 p.m., and concludes at Candlelight South at 8:00 p.m. Each location offers special food and drink deals. To join, purchase a drink at Kaiser's or Sogno to receive a wristband, granting access to the Old Town Connect bus for free transportation throughout the event.
Uptown Block Party
WHEN: The last Thursday of each month | 5:00 to 9:00 p.m.
WHERE: Along San Marco Avenue, from Grove Avenue.
The Uptown Block Party brings St. Augustine's Uptown neighborhood to life with live music, unique shopping, and diverse culinary options every last Thursday of the month. It's a celebration of community spirit through a vibrant mix of activities and attractions.
Tolomoto Cemetery Tour
WHEN: Every third Saturday of the month | 11:00 a.m. to 2:00 p.m.
WHERE: The Tolomoto Cemetery
The Tolomato Cemetery tour presents a fascinating journey through St. Augustine's rich history, dating back to the 18th century. This tour highlights the cemetery's diverse cultural heritage, featuring graves of significant individuals from various ethnic backgrounds, including Spanish, Cuban, Greek, and African origins.
Vilano Beach Artisan Market
WHEN: Every third Saturday of the month | 4:00 p.m. to 8:00 p.m.
WHERE: The Vilano Beach shopping district along Vilano Road.
The Vilano Beach Artisan Market offers a vibrant showcase of creativity, featuring over 20 vendors presenting an array of artisan-made goods. This lively outdoor market delights visitors with a diverse selection of items, from unique artwork and home décor to handcrafted jewelry and clothing, all accompanied by live local music and a variety of fine wines and craft beers.
Cruisers Car Club Cruise-In
WHEN: Every third Saturday of the month | 5:00 p.m. to 7:00 p.m.
WHERE: The Classic Car Museum at 4730 US-1 in St. Augustine, FL 32086
The St. Augustine Cruisers Car Club (SAC) is a family-oriented organization founded in the mid-90s by four car enthusiasts who loved classic vehicles. It has grown into a 501(c)4 non-profit with over 120 member families who share a passion for cars. SAC participates in various events and civic gatherings, where their club cars are displayed, generating enthusiastic interest and sparking
numerous questions from attendees, both young and old. The monthly cruise-in is a chance to socialize, connect with SAC members, and discuss the classics, including those memorable ones you wish you'd never sold.
St. Augustine Wine Walk
WHEN: Every third Thursday of the month | 6:00 p.m. to 8:30 p.m.
WHERE: 57 Treasury Street in historic downtown St. Augustine.
The St. Augustine Wine Walk, organized by Casa de Vino 57, offers an enchanting wine-tasting experience, guiding participants through a series of local shops for tastings. This event culminates with a serene glass of wine in the charming courtyard of Casa de Vino 57.
Nocatee Farmer's Market
WHEN: Every third Saturday of the month | 10:00 a.m. to 1:00 p.m.
WHERE: Nocatee Station Field, 400 Nocatee Center Way, Ponte Vedra, Florida 32081
The Nocatee Farmers Market is a lively community gathering featuring an array of unique vendors. Attendees can explore a selection of fresh fruits, homemade goods, and numerous family-friendly activities, offering an authentic market experience enriched with local charm.
GTM Research Reserve Guided Exploration Hike
WHEN: Every first Saturday of the month | 9:00 a.m. to 11:00 a.m.
WHERE: GTM Visitor Center
The GTM Research Reserve Guided Exploration Hike, held on the first Saturday of each month, offers an enriching experience for nature enthusiasts. Participants will embark on a 2.2-mile hike led by a GTM naturalist, exploring the diverse flora and fauna of the Guana Peninsula and delving into its 5,000 years of human history, including insights into Native American life and the European plantation era.