Great American Scarecrow Festival
2025-09-28 12:00 - 16:00 (America/New_York) | The Feed Mill, 6400 CR 214, St. Augustine, 32092, United States
Great American Scarecrow Festival
Be sure to join us at The Feed Mill for an afternoon of fun! To celebrate Pie in the Sky’s Sweet Sixteen anniversary, we’re bringing this popular event back!
When: Sunday, September 28, 2025 — 12:00pm-4:00pm
Proceeds support Pie in the Sky’s mission to fight senior hunger!
You’ll enjoy …
* Scarecrow building
* Live music with the Thick & Thin String Band — 1:00pm-4:00pm
* Fire grilled pizza
* Games galore
* Bake sale (order ahead)
* Face painting ….
* and more!
Click the event website link for additional details. Questions? Call 904-217-4863.

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.

Wednesday Pier Farmers Market
2025-10-01 08:00 - 12:00, 2025-10-08 08:00 - 12:00, 2025-10-15 08:00 - 12:00, 2025-10-22 08:00 - 12:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine, 32080
Stop by the St. Augustine Beach Pier Park for the Wednesday Pier Farmers Market. You’ll find quality goods at affordable prices. Learn something new from a farmer, grower, or local artist!
Live Local – Shop Local!
Vendors include: farms, hot foods and food trucks, grocery and prepared foods, personal care items as well as arts & crafts.
Pet-friendly market.
Market Hours
May through October: 8:00am – 12:00pm
November through April: 8:00am – 1:00pm
For more information, click on the event website link or call 904-315-0952.

Sizzlin' Soirée Benefit
2025-10-02 18:00 - 21:00 | Fountain of Youth Archaeological Park, 11 Magnolia Avenue, St. Augustine, FL, 32084, United States
Join us for the 4th annual Sizzlin’ Soirée Benefit! Enjoy a night filled with fun, camaraderie, and giving back … all in support of a great cause! All proceeds directly benefiting the young people at THE PLAYERS Championship Boys & Girls Club in St. Augustine. Invest in our local St. Augustine young people!
When: Thursday, October 2, 2025 — 6:00pm-9:00pm
Where: Fountain of Youth
Silent and Live Auction * Music * and More
Click the event website link for all additional information as it becomes available … including tickets and Sponsorship opportunities.

Live Music at Funkadelic Food Shack
2025-10-03 17:30 - 20:30, 2025-10-10 17:30 - 20:30, 2025-10-17 17:30 - 20:30, 2025-10-24 17:30 - 20:30 | Funkadelic Food Shack, 4225 A1A S., Ste A, St. Augustine, 32080, United States
Join us for Live Music at Funkadelic Food Shack every Friday … 5:30pm-8:30pm! Grab a bite to eat while you’re here.

Amphitheatre Farmers Market
2025-10-04 08:30 - 12:30, 2025-10-11 08:30 - 12:30, 2025-10-18 08:30 - 12:30, 2025-10-25 08:30 - 12:30 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
Stop by the St. Augustine Amphitheatre on Saturdays for the Farmers Market … 8:30am-12:30pm. You can select from a variety of fresh food, artisan goods, flowers, and local art. And, you can also enjoy live entertainment on the Front Porch.
Free Admission ** Free parking at The Amp,the Elks Lodge, and the front paved lot at R.B. Hunt Elementary School.
No Pets please!
The St. Augustine Amphitheatre Farmers Market is a Green Market! So, please bring reusable shopping bags and/or containers. Or, you can purchase one of their reusable totes.
You SNAP, We Match! Swipe your SNAP card and receive up to $40.00 extra to buy Florida-grown fruits and vegetables.
Click event website link for full details.

CROCtoberfest Brew at the Zoo 2025
2025-10-04 18:00 - 21:00 | St. Augustine Alligator Farm Zoological Park, 999 Anastasia Blvd., St. Augustine, FL, 32080, United States
CROCtoberfest Brew at the Zoo 2025
The St. Augustine Alligator Farm Zoological Park is hosting their annual CROCtoberfest Brew at the Zoo the first weekend of October. A portion of the proceeds benefit conservation partners.
When: October 4, 2025 from 6:00pm-9:00pm.
Sample beers from Florida breweries while learning about conservation work happening right here in St Johns County from our Conservation partners. Local restaurants on hand with some of their favorite dishes. Live music throughout the park!
The full list of participating breweries, restaurants, conservation organizations, and musicians is posted at the beginning of each September.
Strictly 21 years of age and older. No children – including infants or toddlers – or pets! Access to enter is available until sunset.
Tickets go on sale in late Summer! Free parking at the Alligator Farm.
Click event website link for all the details and to purchase your admission ticket!
Image used is from the Alligator Farm website.

National Night Out 2025
2025-10-07 17:00 - 20:00 | St. Augustine Beach Pier, 350 A1A Beach Blvd, St. Augustine, 32080
National Night Out 2025
Join us at the St. Augustine Beach Pier for National Night Out 2025. Bringing the community together for a night of fun! Sponsored by your local Law Enforcement Agencies and Fire Departments.
When: Tuesday, October 7, 2025 — 5:00pm-8:00pm
There will be: Music * Goodie Bags for Kids * Raffles * Exhibitors/Vendors * Free Food * Law Enforcement Personnel * Non-Profits

66th Annual Cracker Day 2025
2025-10-11 09:00 - 16:00 | St. Johns County Fairgrounds, 5840 State Road 207, Elkton, FL, 32033
66th Annual Cracker Day 2025
Head to the St. Johns County Fairgrounds on Saturday, October 11, 2025 for the annual Cracker Day! Market and Activities 9:00am-4:00pm.
The Horse Games and Festival are sponsored by the St. Johns County Cattlemens’ Association and reflects the county’s agricultural history. Watch and learn about the Cracker Cattle and cowboy history.
Plenty of horses and horse races/games. Fun for all ages! Pets are welcome.
Horse Games Info
Poles * Pick Up Race * Arena Race * Barrels ** Jackpot Barrels & Jackpot Poles
Registration to compete in Horse Games: $5.00-$15.00
Additional Activities
Farmer’s Market with Arts & Crafts, Blacksmithing, Honey & Datil Products, Boutiques & Woodworking, Pony Rides & Petting Zoo, Snow Cones & Ice Cream … and Much More.
Parking: $5.00 per Vehicle – Cash Only
Click the event website link for all the details. Questions? Call 904-669-5157.
Image used is from St. Johns County Cattleman’s Association Facebook.

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.

Nocatee Farmers Market
2025-10-18 10:00 - 13:00 | Nocatee Station Field, 245 Nocatee Center Way, Ponte Vedra, FL, 32081, United States
Come out to the Nocatee Farmers Market at Nocatee Station Field — the 3rd Saturday of the month from 10:00am-1:00pm.
Shop from 70+ local vendors. Browse fresh produce, handmade crafts, jewelry, herbs, unique foods, and more And, Blue Water Bar and Grill will be open for food and drink purchases to enjoy while shopping at the market.
The event is weather-permitting.

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!

Vilano Beach Artisan Market
2025-10-18 16:00 - 20:00 | Vilano Beach Main Street, 101 Vilano Road, St. Augustine, FL, 32084, United States
Head to Vilano Beach on the 3rd Saturday of the month for the Artisan Market — 4:00pm-8:00pm. Celebrate local artisans and entrepreneurs! Please Note: there will be no Artisan Market in October … you’ll want to head to the Vilano Vibe-Rations Music Festival 2025 instead.
Check out the crafts, goods and services offered by local entrepreneurs. Starting in May, the Artisan Market will be set up on the West end of Vilano Road, starting near the Vilano Beach Pier. This will help make the market more spacious for everyone.
Come find some of the most unique and cool items from local favorites. From handmade jewelry, handcrafted bags, local baked goods and so much more! Vendors vary each month and can include everything from local honey to macrame to jewelry to high-tech lights for private docks.
Vilano Beach Main Street also hosts a cash beer/wine bar so you can sip while you shop.
Come out and CATCH THE VIBE!
For information, email vilanomarketwalk@gmail.com

2026 Pin Up Paws Calendar Party
2025-10-23 18:00 - 21:30 | The White Room, 1 King Street, St. Augustine, FL, 32084, United States
Join us for the 2026 Pin Up Paws (PUP) Calendar Party where “The Gilded Paw” calendar is revealed! Find out whose pet “won” the ‘Grand Masterpiece’ cover and whose is a celebrated portrait of the month.
When: Thursday, October 23, 2025 — 6:00pm-9:30pm
Where: The White Room
Enjoy a delicious dinner, complimentary wine, cash bar, music by the House Cats jazz quartet, silent auction, wine pull, photo booth, caricature artist, and a free copy of the 2026 A Gilded Paw calendar.
Free parking is available nearby at Trinity Parish Parking Lot.
Tickets: $135.00 per person | pricing per table also available
Click the event website link for all the de”tails” and to purchase your tickets. Tickets also available at the Front Desk of the Humane Society.
This event is the largest fundraising effort the Humane Society hosts each year. All of the money raised will directly benefit our lifesaving programs and resources which provide care to the pets who need it most.

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.

Rooted in Excellence Fall Harvest Dinner
2025-10-24 18:00 | Michael’s, 117 Vilano Road, St. Augustine, FL, 32084, United States
You are invited to the Rooted in Excellence Fall Harvest Dinner. This signature dinner series is in partnership with the Friends of James Beard Foundation and benefits Pie in the Sky Community Alliance.
Rooted in Excellence brings together acclaimed chefs, local farmers, and passionate supporters to celebrate our region’s culinary spirit while providing fresh, healthy food to low-income seniors in St. Johns County through Pie in the Sky’s essential programs.
When: October 24, 2025 — 6:00pm
Where: Michael’s Private & Main Dining Rooms … for an intimate gathering of 100 guests
Cost: $250.00 per guest … includes multi-course dinner, thoughtfully paired wines, and a portion supporting Pie in the Sky’s mission.
Click the event website link to purchase your ticket(s).
