St. Augustine, FL | Oldcity.com

Pumpkin Festival + Handmade Market
2025-09-27 09:00 - 17:00 (America/New_York) | 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.

St. Augustine Songwriters Festival 2025
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.

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, 2025-11-08 14:00 - 17:00, 2025-11-09 10:30 - 14:00 | 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, 2025-11-09 10:00 - 15:00 | 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

Lullaby of the Rivers Pop-Up Festival
2025-11-22 11:00 - 17:00 | Limelight Theatre, 11 Old Mission Avenue, St. Augustine, FL, 32084, United States
Lullaby of the Rivers Pop-Up Festival
Join us at the Limelight Theatre for the “Free” Lullaby of the Rivers Pop-Up Festival. There will be outstanding entertainers in musical traditions of folk, Americana, jazz, and blues providing memorable performances! Along with vendors and exhibitors.
When: Saturday, November 22, 2025 — 11:00am-5:00pm
Where: Limelight Theatre Parking Lot
The All-star lineup includes the likes of:
* Acoustic Anomaly
* Bad Dog Mama
* Bear & Robert
* Buffalo Rose
* Dave Besley & Sue Wescott
* Duffy Bishop Band
* John Dickie IV
* Katherine Archer
There will be exhibitors on hand teaching people about the environment, especially Florida’s rivers, and explore how nature inspires the arts. They include:
* NE Florida Sierra Club
* Bee Augustine
* Lullaby of the Rivers
* and others
Activities and workshops invite the whole family to participate. Bamboo river sticks are a festival favorite, cut to size and ready to personalize while learning how to use them. Vendors offer an array of their own nature-inspired wares and provide favorite festival foods and beverages.
Stick around afterwards for the premier of Ancient City Limits Concert, a ticketed event in the Limelight’s Black Box.

Christmas Experience at Ancient City Farmstead
2025-11-28 17:00 - 21:00, 2025-11-29 15:00 - 21:00, 2025-11-30 15:00 - 21:00, 2025-12-05 17:00 - 21:00, 2025-12-06 15:00 - 21:00 | Ancient City Farmstead, 395 St Marks Pond Blvd, St. Augustine, FL, 32095, United States
Christmas Experience at Ancient City Farmstead
St. Augustine’s ultimate Christmas Experience returns to Ancient City Farmstead! Head to this holiday spectacle so packed with family fun that you’re liable to find yourself on the naughty list!
When: Weekends – November 28-December 21, 2025 || Fridays — 5:00pm-9:00pm | Saturdays and Sundays — 3:00pm-9:00pm
Christmas Wonderland Features Fun for All:
🎄 Experience nightly lighting ceremonies of the region’s tallest decorated Christmas tree. It’s just like Rockefeller Center without the trip to NYC!
🎅 Visit Santa in his workshop to make sure you’ve secured your spot on the nice list! Be sure to tell him everything you want this Christmas.
🔥 Roast marshmallows over the giant fire pit with friends, old and new.
🫎 Compete in free reindeer games and win prizes.
☕️ Sip on hot cocoa and snack on seasonal concessions.
🌲 Take the festive feeling home when you pick out the perfect Christmas tree from the forest of 2,000+ spruce trees.
⛸️ Lace up your skates and flaunt your stuff on Florida’s only outdoor skating rink!
Photo ops … Memories to last a lifetime abound.
Free onsite parking.
Cost:
$25.00 — Adults – ages 16-65
$20.00 — Seniors & Military w/Military ID
$15.00 — Children – ages 3-15
Free — Children under 3
To give your family the ultimate Christmas Experience click the event website link to get your tickets now!

Gullah Geechee Heritage Festival 2025
2025-12-06 12:00 - 17:00 | Armstrong Park, 4950 Harvey Avenue, Elkton, FL, 32033, United States
Gullah Geechee Heritage Festival 2025
Join us for the 12th annual Gullah Geechee Heritage Festival! Immerse yourself in authentic Gullah Geechee culture and heritage! Traditional Music, Dance, Foods and Crafts!
Start your day with the Rails to Trails Bicycle Tour at 9:00am (click event website link for details as they become available).
When: Saturday, December 6, 2025 — 12:00pm-5:00pm
Where: Armstrong Park
Celebrating 451 years of West African influence in St. Johns County!
Free and family-friendly! That includes well-behaved, leashed dogs. Entertainment and activities for ALL ages!
Performers include …
* Gullah Geechee Ring Shouters
* El Shaddei Dance Ministry
* Str8up Jax
* Marcellaus Brown’s Band
* JW Gilmore & The Blues Authority
There will also be various exhibitors on hand.
Food and beverage available for purchase.
This event benefits the SEA Community Resource Center.
Click the event website link for all additional information.
