It Finally Feels Like Fall 🍂 Pumpkins, Sheep and Food Trucks

It is finally cooling down this weekend, and it is actually going to feel like fall. 🍂 Perfect timing, because Food Truck Friday is back on the Station Field with Bold City Classics playing, and Saturday brings the first proper pumpkin outing of the season at the Wesley Wells Pumpkin Festival plus a gentle morning with the sheep at Shanty & Co. Three easy ones to build the weekend around 👇

Food Truck Friday
📍 Nocatee Station Field (Cartable 🛒)
🕐 5:30 PM – 8:00 PM | Friday
🎟️ Free
👪 All ages
🔗 More info here

Food trucks on the Station Field with Bold City Classics playing and Blue Water Bar and Grill open for drinks and bites. Bring chairs, a blanket and bug spray. Close enough to take the cart, and there is a separate 21+ area if the grown-ups want one.

Pumpkin Festival & Handmade Market
📍 Wesley Wells Farms (~39 min 🚗)
🕐 9:00 AM – 4:00 PM | Saturday
🎟️ See event link
👪 Children & families
🔗 More info here

Pumpkins, a handmade market and fall activities out at the farm. It is the first real pumpkin-patch weekend of the season, and a long enough drive that it is worth making the morning of it.

Fall Meet & Greet With Sheep
📍 Shanty & Co. (~33 min 🚗)
🕐 10:00 AM – 1:00 PM | Saturday
🎟️ See event link
🧒 Young children
🔗 More info here

Hands-on time with the sheep at a small local farm, about as gentle an animal experience as you will find for little ones. With the cooler air rolling in, it is the ideal slow Saturday morning outing.

Clay Creations
📍 Creative Me Art Studio (~24 min 🚗)
🕐 4:00 PM – 5:15 PM
🎟️ $17 per child
🧒 Ages 5–7
🔗 More info here

The weekly after-school clay class: sculpt, paint and decorate an air-dry project that goes home the same afternoon. RSVP online before you go.

Bring a Board Family Night
📍 Family Church (~33 min 🚗)
🕐 5:00 PM
🎟️ Free
👪 Children & families
🔗 More info here

Bring a board game and a snack board. Families play, share and eat their way through a relaxed evening together.

Dessert Party with Alice & the Mad Hatter
📍 Ready Set Play (~37 min 🚗)
🕐 5:00 PM – 6:30 PM
🎟️ $24.95 per child / $3 adult
🧒 Young children
🔗 More info here

Wear your best hat to meet Alice and the Mad Hatter over desserts and drinks, with open playtime alongside the party.

Food Truck Friday
📍 Nocatee Station Field (Cartable 🛒)
🕐 5:30 PM – 8:00 PM
🎟️ Free
👪 All ages
🔗 More info here

Food trucks on the Station Field with Bold City Classics playing and Blue Water Bar and Grill open. Chairs, blankets and bug spray recommended; there is a separate 21+ area for the grown-ups.

Kids Night Out
📍 Creative Me Art Studio (~24 min 🚗)
🕐 6:00 PM – 9:00 PM
🎟️ $40–$45
🧒 Ages 5–18, grouped by age
🔗 More info here

Three hours of art project, movie and pizza dinner while you get a kid-free evening. Groups run 5–7, 8–10, 11–15 and 15–18.

Monthly Beach Cleanup
📍 GTM Research Reserve Visitor Center (~23 min 🚗)
🕐 9:00 AM – 11:00 AM
🎟️ Free
👪 All ages
🔗 More info here

Meet at the Visitor Center at nine for a short orientation; gloves and bags are provided. No signup needed, just turn up ready to help.

Pumpkin Festival & Handmade Market
📍 Wesley Wells Farms (~39 min 🚗)
🕐 9:00 AM – 4:00 PM
🎟️ See event link
👪 Children & families
🔗 More info here

Pumpkins, a handmade market and fall activities out at the farm. The first proper pumpkin-patch weekend of the season.

Kids in the Park! Music & Crafts
📍 Canopy Shores Park, 804 Christina Dr, St. Augustine (~45 min 🚗)
🕐 10:00 AM – 11:00 AM
🎟️ $25 per child
👶 Babies & toddlers
🔗 More info here

An hour of music, storytelling, sensory play and fall crafts led by local performers, pitched squarely at the littlest ones.

Fall Meet & Greet With Sheep
📍 Shanty & Co. (~33 min 🚗)
🕐 10:00 AM – 1:00 PM
🎟️ See event link
🧒 Young children
🔗 More info here

Hands-on time with the sheep at a small farm, which is about as gentle an animal experience as you will find for young kids.

Give Kids the World Poolside Party
📍 Guy Harvey Oceanfront Resort, St. Augustine Beach (~45 min 🚗)
🕐 11:00 AM – 4:00 PM
🎟️ Free
👪 Children & families
🔗 More info here

The 28th annual fundraiser: family activities, raffles, auctions, food and photo ops, all of it funding free holidays for children with critical illnesses.

Family Friendly Project Workshop
📍 Board & Brush, 530 State Rd 13 N, St. Johns (~27 min 🚗)
🕐 1:00 PM – 4:00 PM
🎟️ $30+
🧒 Parent, teen & child workshop
🔗 More info here

Parents and kids build and finish a wood project together, with materials and step-by-step instruction provided. Everyone takes their piece home.

Friendship Tour: Girl Scout Information Party
📍 Bartram Trail Branch, 60 Davis Pond Blvd (~27 min 🚗)
🕐 1:45 PM – 3:00 PM
🎟️ Free
🧒 K–1st grade girls & a caregiver
🔗 More info here

An hour and a bit of crafts, games and friendship activities so the youngest girls and their grown-up can see what Girl Scouts actually involves.

Teen Art with Kasha
📍 Bartram Trail Branch, 60 Davis Pond Blvd (~27 min 🚗)
🕐 2:00 PM – 4:00 PM
🎟️ Free | Almost full
🧒 Ages 13–18+
🔗 More info here

Two hours of technique and making with instructor Kasha, all skill levels welcome. Worth booking today: there was a single seat left at the time of writing.

Kids Maker Madness
📍 Ponte Vedra Beach Branch, 101 Library Blvd (~19 min 🚗)
🕐 3:00 PM – 4:00 PM
🎟️ Free
🧒 Ages 6–11
🔗 More info here

The monthly Maker Lab session, with a different set of equipment and projects each time. The month's project is posted in the children's area beforehand.

Glow Dance & Dine
📍 425 South Legacy Trail, St. Augustine (~25 min 🚗)
🕐 5:00 PM – 9:00 PM
🎟️ $25 per child
🧒 Young children
🔗 More info here

Four hours of glow dancing, entertainment and dinner run by the MCA Mustangs dance team, which doubles as a parents' night out.

Moonlight Hike
📍 GTM Research Reserve (~23 min 🚗)
🕐 8:00 PM – 10:00 PM
🎟️ $10+
👪 Children & families
🔗 More info here

After-hours access to the reserve under the full moon, self-guided and quiet. Best for older kids who will not mind the dark and the pace.

Art & Bark in the Park
📍 City of St. Augustine Beach (~43 min 🚗)
🕐 11:00 AM – 4:00 PM
🎟️ Free
👪 Children & families
🔗 More info here

Local artists and artisans, food vendors, live music and animal rescue groups, all in one park. Free, and the dogs are the point as much as the art.

St. Augustine Record Fair
📍 St. Augustine Amphitheatre, 1340C A1A South (~39 min 🚗)
🕐 11:00 AM – 5:00 PM
🎟️ Free
👪 All ages
🔗 More info here

Dozens of vendors, onsite screen-printing, food trucks and live sets from DJ Josh Aaron, Toxic Cats and Bears & Lions. Part of the Sing Out Loud Festival and free to walk into.

St. Augustine Songwriters Festival
📍 Multiple venues, historic downtown St. Augustine (~33 min 🚗)
🕐 Thursday 24 – Sunday 27
🎟️ Free
👪 All ages
🔗 More info here

Nashville songwriters playing intimate acoustic sets in downtown venues and telling the stories behind the songs. Free, and easy to drop into for half an hour.

Ancient City Con
📍 World Golf Village Renaissance Resort, 500 S Legacy Trail (~26 min 🚗)
🕐 Friday 25 – Sunday 27
🎟️ Ages 7 and under free with a paying adult | See site for pricing
👪 Children & families
🔗 More info here

Celebrity guests from film, TV, comics and games, plus cosplay, gaming, vendors and artists across the weekend. Under-7s get in free with a paying adult; the organisers note not every panel suits every age.