St. Augustine, FL | Oldcity.com

Sing Out Loud Festival 2025
2025-09-13 15:30, 2025-09-14 13:00, 2025-09-18 18:00, 2025-09-19 16:30, 2025-09-20 15:00, 2025-09-21 14:00 (America/New_York) | Various Locations in St. Augustine, St. Augustine, FL, 32084, United States
Sing Out Loud Festival 2025
September in St. Augustine brings the annual Sing Out Loud Festival. Enjoy live music performances at multiple venues on long weekends in September … 5-7, 12-14, & 18-21.
Featuring performances by local, regional, and national acts! And … many of the events are Free!
The big event requiring a ticket purchase is:
* Live Wildly Showcase at Francis Field on September 20 & 21
Other venues include: Colonial Oak Music Park, Prohibition Kitchen, St. Augustine Distillery, and Tradewinds Lounge among others.
Additional events under the festival’s ‘umbrella’: Sing Out Loud Music Business Panel * An Evening with Chuck Leavell (paid event) * St. Augustine Songwriters Festival * St. Augustine Record Fair
Sing Out Loud Festival App Info
Be sure to download the free Sing Out Loud Festival app today via the App Store for iOS or Google Play Store for Android devices. It’s packed with info that includes venue and vendor information, personalized schedules, artist playlists, Spotify integration, and more. The app’s real-time updates keep users informed of any last-minute changes, such as venue shifts or time adjustments.
Times vary by day. Be sure to click the event website link for all the details .. that includes the performers and performance schedule.
Image used is from the Sing Out Loud Festival website.

St. Augustine Book Festival
2025-09-20 10:00 - 16:00 | Ximenez-Fatio House Museum, 20 Aviles Street, St. Augustine, FL, 32084, United States
Stop by the courtyard of the Ximenez-Fatio House Museum for their 3rd annual St. Augustine Book Festival. Free and Open to All!
When: Saturday, September 20, 2025 — 10:00am-4:00pm
Discover a wide variety of authors and genres … including children’s books, fiction, Florida history, and more.
Enjoy author ‘Meet and Greets’ * Explore exciting new works.
Donations greatly appreciated to support the preservation of the Museum
Click the event website link for all additional details.

2025 Live Wildly Showcase
2025-09-20 14:00, 2025-09-21 16:00 | Francis Field, 25 W. Castillo Drive, St. Augustine, FL, 32084, United States
Sing Out Loud Festival 2025 Live Wildly Showcase
September brings the 9th annual Sing Out Loud Festival to St. Augustine with live music performances at multiple venues. Featuring performances by local, regional and national acts! And … many of the events are Free!
One of the paid events is the Live Wildly Showcase … a 2-day concert event at Francis Field on Saturday and Sunday, September 20 & 21. The showcase pairs an exceptional roster of artists with the mission of raising funds for land conservation in Florida.
This years’ Live Wildly Showcase features:
Saturday, September 20, 2025 Lineup

* Indie dream-pop phenom Beabadoobee
* Chart-topping folk-pop artist Vance Joy
* Enigmatic singer-songwriter Father John Misty
* The dynamic and boundary-breaking Maren Morris
* Viral star David Kushner
* Rising left-field pop singer Sarah Kinsley
Sunday, September 21, 2025 Lineup
* International platinum-selling artist Hozier
* Soulful blues duo The Teskey Brothers
* Beloved indie rock band Rilo Kiley
* The heartfelt songstress Gigi Perez
* Breakout alternative star sombr
* Viral folk pop artist Brenn
Ticketing Information
Specially priced Early Bird Tickets go on sale to the general public on Friday, February 21, 2025 at 10:00am through the festival’s official ticketing partner, AXS.
Tickets for single-day and two-day General Admission, General Admission Plus, and Platinum tickets will be available on the Festival’s website, through AXS, or at the St. Augustine Amphitheatre Box Office, open daily from 7:00am to 5:00pm.
Click the event website link to purchase your “showcase” tickets and for all additional details.
Please note: times are tentative

St. Augustine Songwriters Festival 2025
2025-09-26 11:00, 2025-09-27 11:00, 2025-09-28 11:30 | FL
St. Augustine Songwriters Festival 2025
Mark your calendars for the St. Augustine Songwriters Festival … September 26-28, 2025! Featuring today’s hottest hit songwriters, the legends of yesterday and the stars of tomorrow. Just one of the events during the Sing Out Loud Festival.
Hear the songs that you know and love or that you sing in the car or shower from their creator. Learn the inspiration that brought them to life. Find out or meet who the song was written for or about.
The festival will feature over 30 artists whose works have reached the pinnacle of the charts and numerous accolades. A few of the hit songwriters that will be making an appearance are Rodney Clawson, Jon Nite, Adam Wood, Kristen Merlin, Lost Saints, Halfway to Hazard, Davis Loose, Cliff Cody …and more!
Performances Locations: Colonial Oak Music Park, Prohibition Kitchen, Trade Winds Lounge, and St. Augustine Distillery
Performance line-up and times are subject to change. Check out the event website for updated information and to purchase your tickets.

Pumpkin Festival + Handmade Market
2025-09-27 09:00 - 17:00 | Wesley Wells Farm, 2680 Ada Arnold Road, St. Augustine, FL, 32092, United States
Pumpkin Festival + Handmade Market
Join us at Wesley Wells Farm for the annual Pumpkin Festival + Handmade Market! Pick your own pumpkin right off the vine along with you-pick veggies and flowers … and so much more!
When: Saturday, September 27, 2025 — 9:00am-5:00pm
Activities for All
* Pick Your Own Pumpkins, Veggies & Flowers
* Farm Animals
* Photo Ops
* Hay Rides
* Crop Maze
* Local Vendors
* Food Trucks
* Kid Zone
* and more
Tickets*: $18.00 per person at the gate | $15.00 per person online
*Tickets do not include u-pick pumpkins, veggies or flowers. Those can be purchased at the farm.
Click the event website link for all the details and to purchase your tickets in advance.
Image used is from Wesley Wells Farm website.

Fall Fling Festival
2025-09-28 12:00 - 17:00 | St. Augustine Rod & Gun Club, 401 Gun Club Road, St. Augustine, FL, 32095, United States
Fall Fling Festival
Be sure to get ready for a day of fun and philanthropy at the Fall Fling Festival! Hosted by St. Augustine Society.
When: Sunday, September 28, 2025 — 12:00pm-5:00pm
Where: St. Augustine Gun Club
The Gun Club will transform into a vibrant Fall Wonderland where families and friends will come together to enjoy friendly competition, fun and games. All for a good cause … the event is to help raise $10,000 for the Clean Start laundry facilities at the new Goff Family Shelter. This shelter will house nine families with children, offering stability and a safe place to rebuild their lives.
There will be:
Cornhole Tournament * Hayrides * Games * Pumpkin/Face Painting * Live Bluegrass Music by the St. Augustine High School Band * Fall Market * Community Partner Booths * Food Trucks * A Cider Bar * 50/50 Raffle * and More!
Admission: $20.00 – Adults | $10.00 – Kids under 10 | Free – Kid under 3
* Purchase tickets before September 1st and use code FLINGFUN to receive $5.00 off per ticket.
Click the event website link for additional information and to register/pay for the Cornhole Tournament.

St. Augustine Greek Festival 2025
2025-10-11 11:00 - 21:00, 2025-10-12 12:00 - 17:00 | Holy Trinity Greek Orthodox Church, 2940 CR 214, St. Augustine, FL, 32084, United States
St. Augustine Greek Festival 2025
Immerse yourself in Greek culture and heritage at the 27th Annual St. Augustine Greek Festival. Celebrate All Things Greek … authentic Greek food, pastry, music, dancing and more!
When:
Saturday, October 11 — 11:00am to 9:00pm
Sunday, October 12 — 12:00pm to 5:00pm​​​​
Where: Holy Trinity Greek Orthodox Church
Join us for a meal and to celebrate Greek Culture and Heritage!
Shopping opportunities at … the Holy Trinity Agora (market) * St. Theodora’s Gift Shop and Bookstore * the Zaharoplastio (for pastries and treats to take home!)
The Kafenio will be serving up Greek frappes and friendly bartenders will have plenty of ouzo lemonada, beer and wine available for purchase.
Are you interested in ordering pans of Greek Food? Then check out the Menu/Pre-order Page to place your order(s) … now through Friday, October 3, 2025.
Parking | Shuttle Information
* Free parking will be available at Webster Elementary School (420 North Orange St, St. Augustine) with a shuttle will be provided by Old Town Trolley Tours.
* Limited premium parking will be available at Holy Trinity Church for $20.00
Click the event website link for all additional information.

Halfway to SweetWater Music Fest 2025
2025-10-17 16:20 - 23:00, 2025-10-18 12:30 - 23:00, 2025-10-19 12:30 - 22:00 | Colonial Oak Music Park, 33 St George St., St. Augustine, FL, 32084, United States
Halfway to SweetWater Music Fest 2025
Be sure to mark your calendars for the Halfway to SweetWater Music Fest 2025! Jam bands, funk, rock, psychedelic acts, art, fire dancers, burlesque, and more.
When:
Friday, October 17 — Gates Open 4:20pm | Music Til 11:00pm
Saturday, October 18 — Gates Open 12:30pm | Music Til 11:00pm
Sunday, October 19 — Gates Open 12:30pm | Music Til 10:00pm
Where: Colonial Oak Music Park
Highlights Include
* VIP Friday Pre-Party with Steelin’ Peaches, One Good Ring, Rae & The Ragdolls + Dark Side of the Rainbow Laser Burlesque
* Live sets from Andy Frasco & The U.N., Cool Cool Cool, Steeln’ Peaches, One Good Ring, Funk You, Funkin Grateful, and more
* Donation-based Puppy Yoga – benefiting Ayla’s Acres Animal Rescue
* Artisan market, Webber BBQ & Grill Garden, and $4.20 SweetWater beer specials
Ticket Information
One Day, Two Day, Friday Pre-Party, Two-Day Ticket Package, & VIP Tickets available.
Prices range from Friday Pre-Party only at $27.00 to VIP All Weekend Access at $129.60
Click the event website link for all the details (including Know Before you Go) and to purchase your tickets.

Vilano Vibe-Rations Music Festival 2025
2025-10-18 11:00 - 18:30 | Vilano Beach Oceanfront Park, 2725 Anahma Drive, St. Augstine, FL, 32084, United States
Vilano Vibe-Rations Music Festival 2025
‘Catch the Vibe!’ at the Vilano Vibe-Rations Music Festival 2025! Be ready to dance to your hearts content. Come hungry and thirsty as well. It’s going to be a great day filled with music, food, and fun!
Kid & Pet Friendly Atmosphere.
When: Saturday, October 18, 2025 | 11:00am-6:30pm (Gates open 10:45am-6:45pm)
Where: Back lot of the Hampton at Vilano Road and Anahma Dr.
Rock legends and local musicians will be performing throughout the afternoon into the early evening.
Entertainment includes:
* Bad Endings … special guests: Mike Reno (unforgettable voice of Loverboy), Billy Greer (former lead singer of KANSAS), Jeff “Skunk” Baxter (formerly of Doobie Brothers and Steely Dan)
* Brothers Futch
* Those Guys
* Money for Nothing
* Dewey Via Band
There will also be: Gourmet Food Trucks * a 7-Tap Beer Truck with local and national brews * Wine & Signature Cocktails * Bloody Mary Bar
Please bring your own chairs for seating. Coolers are NOT allowed.
Ticket Information:
$75.00 — VIP Experience – includes: Exclusive tented + open-air seating * Air-conditioned restrooms * VIP-only liquor bar * Valet parking available ($15.00) * Hang with the musicians between sets!
VIP only inside the gate. VIP only inside the fence.
Outside of the gate is free!
Free Shuttle Info
A free shuttle will be circulating throughout Vilano Road and the Vilano Town Center area, making it easy for guests to get to and from the festival with ease. Just hop on and catch the vibe—no need to worry about the ride!
Proceeds benefit the Vilano Beach Community.
Click event website link to purchase your tickets and for additional details!

Hasting Fall Festival + Harvest Trail Tour
2025-10-24 11:00, 2025-10-25 10:00 - 16:00 | Main Street in Hastings, Main Street, Hastings, FL, 32145, United States
Hasting Fall Festival + Harvest Trail Tour 2025
Gather your friends, family, and neighbors and head to the Hastings Main Street Fall Festival 2025! And … new for 2025 – there’s a Harvest Trail Tour as well. Celebrate the Fall Season with music, community, and fun!
When: Friday and Saturday, October 24 & 25, 2025
Event Schedule
Friday, October 24 — inaugural Fall Festival Harvest Trail Tour – kicking off at 11:00am (ticketed event)
Explore five unique farms across southern St. Johns County … where agriculture and heritage come together to tell the story of our region’s deep farming roots. See where your food comes from and learn directly from the farmers who work the land. Hands-on! Behind-the-scenes access! Begin at Hastings Nutrition Co and finish at Olive Land Farm … where you’re invited to stay and enjoy an optional add-on dinner featuring authentic paella, delicious sangria, live music and a magical evening under the stars.
Cost: $45.00 for Tour | $35.00 additional for Paella Dinner.
Be sure to click the event website link for a list of participating farms and to purchase your ticket(s).
Saturday, October 25 — Hastings Main Street – Free Admission – 10:00am-4:00pm
Live Music * Cottage Artisan Market * Kids Zone * and More … from Food Trucks to Community Showcases
Click the event website link for all additional information.

St. Benedict the Moor Blues Fest 2025
2025-10-24 16:00 - 22:00, 2025-10-25 16:00 - 22:00, 2025-10-26 11:00 - 15:30 | St. Benedict the Moor Catholic Church, 86 Martin Luther King Jr. Avenue, St. Augustine, FL, 32084, United States
St. Benedict the Moor Blues Fest 2025
October brings us the annual St. Benedict the Moor Blues Fest 2025! Nestled in the heart of the historic district of Lincolnville.
If you enjoy the blues and good food, then St Benedict the Moor Blues Festival is for you! This popular, annual event features Rockin’ Blues music, food, beverages and games at one of St. Augustine’s historical sites. Don’t forget your lawn chairs!
Friday, October 24, 2025 — 4:00pm – 10:00pm
Saturday, October 25, 2025 — 4:00pm – 10:00pm
Sunday, October 26, 2025 — 11:00am – 3:30pm
Music Lineup
Friday, October 24
4:00pm-6:00pm — Ken Jensen Blues Ensemble
6:00pm-8:00pm — Duffy Bishop Band
8:00pm-10:00pm — No Filter Blues Band
Saturday, October 25
4:00pm-6:00pm — Gitlo – Thos. Lee
6:00pm-8:00pm — Hitman Blues Band
8:00pm-10:00pm — JW Gilmore & the Blues Authority
Sunday, October 26 (Gospel Blues Sunday)
9:15am — Arlie Mae Victory
9:45am-11:00am — Americana Gospel
11:00am-12:00pm — Rick Spence Jazz Combo
Cost: $7.00
What makes this festival even more special is its’ noble cause – all proceeds go towards restoring the historic St. Benedict the Moor rectory/church. Attend and support a significant piece of St. Augustine’s rich Catholic heritage!
Click event website link for all additional information and to purchase your admission and food tickets.

Riverdale Community Fall Festival
2025-11-01 11:00 - 15:00 | Riverdale Community Methodist Church, 1028 County Road 13 south, St. Augustine, FL, 32092, United States
Stop by the Riverdale Community Fall Festival nestled along the St. Johns River. You’ll find Live Music, Chili Contest, Hot Dogs & Drinks, Vendors, Game Area, Fall Photo Opportunity, and more.
When: Saturday, November 1, 2025 — 11:00am-3:00pm
Where: Riverdale Community Methodist Church
Free to attend! Free parking.

Whiskey, Wine & Wildlife Event 2025
2025-11-07 18:30 - 20:30, 2025-11-08 10:00 - 12:00 | FL
Whiskey, Wine & Wildlife Event 2025
Mark your calendars for November 7-9, 2025 for this annual event! W3 is a culinary weekend like no other blending food & drink lovers with the surrounding beauty of nature! Raising funds and awareness for Vilano Beach Main Street and the St. Augustine Alligator Farm Zoological Park.
Enjoy beverage tastings artfully combined with inspired cuisine from some of the South’s best chefs as well as local culinary superstars. And, education experts are on-hand Friday and Saturday, showcasing some fun, interactive programs with coastal wildlife, from alligators to reptiles.
Please Note: Attendees must be of legal drinking age or older to attend most events. No dogs or pets allowed.
Events are rain or shine and programs are subject to change without notice.
Event Info | Schedule:
Friday, November 7
* 6:30pm-8:30pm Dinner – Vilano A1A Soirée – Hyatt Place St. Augustine/Vilano Beach. A tasting event – indoors and out – with gourmet bites. Sample some of NE Florida’s best restaurants, live music and more. Guests receive souvenir glass for unlimited beer, wine and spirits tastings.
Saturday, November 8
* 10:00am – 12:00pm – Alligator Farm VIP Behind the Scenes Tour – St. Augustine Alligator Farm Zoological Park. Guests are treated to a guided, behind the scenes, private tour … with special access to several exhibits. A tour of the “Rookery” is also included where native herons, egrets, spoonbills, and wood storks can be seen. Private Wine & Cheese Reception at the conclusion. Rain or shine.
* 2:00pm – 5:00pm – W3 Main Event – Whiskey, Wine & Wildlife Block Party – Hyatt Place St. Augustine/Vilano Beach. All three of the W’s and much more including: culinary delights from the A1A Corridor – some of northeast Florida’s best * hundreds of unlimited varieties of beverage tastings (spirits, wines and beers) with a souvenir glass * live music * wildlife and educational demonstrations from St. Augustine Alligator Farm.
Sunday, November 9
* 10:30am-12:00pm & 12:15pm-2:00pm (2 seatings) – W3 Sunday Jazz Brunch at Pesca by Michael’s. Grand Finale Brunch. Indoor. Enjoy a generous array of chef-attended stations, offering elegant, seasonal fare; souvenir glass with unlimited beverage tasting stations, and live piano music by Jolie.
Satellite Parking/Shuttle Service Information
Old Town Trolley will be providing Free shuttle service making it the best and most hassle-free way to attend Saturday’s Main Event. Every 30 minutes to and from St. Johns County parks on A1A to Vilano Beach. The schedule is available on the festival website.
Click the event website link to purchase your tickets and for all additional details, including parking and shuttle information.

Historic Lincolnville Festival 2025
2025-11-07 19:00 - 23:00, 2025-11-08 12:00 - 22:00 | FL
Historic Lincolnville Festival 2025
Be sure to save the dates for the Historic Lincolnville Festival … Continuing the Legacy Again! November 7-9, 2025.
Festival Schedule
Friday, November 7 — 7:00pm-11:00pm
The festival kicks off with Veterans/Jazz Night with Doug Carn and his band headlining. Come help celebrate the reopening of the historic Fountain of Youth Elks Lodge on 100 Washington St.
Tickets can be purchased at at 83 Washington Street. They will include 1 free drink Friday night as well as free entrances into the 3 museums in Lincolnville on Friday only from 10:00am-4:00pm.
Tickets: $30.00 — Adults only
Saturday, November 8 — 12:00pm-10:00pm — 100 – 102 M L King Ave
12:00pm-2:00pm — Young people stage, Game trucks & Activities
2:00pm-10:00pm — Live Music featuring:
* Al & Anthony Jazz
* Heart of Elaine
* The Soulful Roots
* Cellus (Afrobeats Artist)
* King Jay Da Blountman
Sunday, November 9 — 10:00am-3:00pm — 101 M L King Ave
10:00am-12:00pm — Gospel Jazz, Coffee & Danishes
1:30pm-3:00pm — Gospel in the Park
Vendors on hand both Saturday and Sunday with clothes, jewelry, candles, body products, purses and handbags, accessories, and more.
Questions? Call 904-504-4251
