Pet policies are not specified—contact the organizer at wesleywellsfarms@gmail.com to confirm before bringing animals.

St. Augustine Pumpkin Festival at Wesley Wells Farm: U-Pick Pumpkins, Hayrides & Local Makers

Read the full experience

On a clear September Saturday, Wesley Wells Farm throws a one-day fall festival just outside St. Augustine, Florida. The 5th Annual Pumpkin Festival transforms the largest you-pick farm in St. Johns County into a lively community fair, where rows of orange pumpkins, seasonal flowers, and vegetable beds replace the quiet of weekday farmwork. From 9:00 AM to 4:00 PM on September 26th, families gather on the farm's fields for hay rides, live music, whip-cracking demonstrations, and a handmade market that pulls together local makers and food trucks. What makes this festival particular to the region is its working-farm setting: broad pick-your-own plots and open-air vendor spaces give visitors a chance to connect with the agricultural rhythm of Northeast Florida. Kids tromp through the kids zone, turning pumpkin selection into a scavenger hunt; adults browse booths for crafts, small-batch goods, and farm-to-table snacks. The festival supports local growers—u-pick pumpkins, flowers, and vegetables are available for an additional fee at the front gate—and invites community vendors to apply by submitting photos to [email protected] for approval. Practical touches keep the day moving. Hay rides circle the property, providing vantage points across the planted rows and a relaxed way to view the farm. Live entertainment stages and food trucks cluster near the market, making it easy to pace an afternoon between browsing and sampling. The whip demonstration adds regional color—a skill-based display rooted in working-farm traditions—while the handmade market highlights artisans whose goods pair well with a slow, outdoor day. If you’re planning a visit, expect family-friendly energy more than rugged trail conditions: stroller- and kid-friendly walking across grassy and sometimes uneven ground. Bring cash if you prefer small vendors, sun protection for mid-September heat, and a vehicle with room for an armful of pumpkins. Vendors are advised that booking includes a standard 12x12 outdoor space only; tents and tables are the vendor’s responsibility. Why come? The festival is a local-sized celebration with the feel of a country fair and the authenticity of an active pick-your-own farm. It’s an easy day trip from St. Augustine for people who want to buy fresh farm produce, discover regional artisans, and let kids run while music plays in the warm Florida air. For vendors and visitors alike, the Wesley Wells Farm Pumpkin Festival is a deliberate, sunlit slice of county fair culture—rooted in soil, season, and community. Check-in details list the festival on Saturday, September 26th from 9:00 AM to 4:00 PM; the meeting point is Wesley Wells Farm and vendors must upload photos for application consideration. Questions about vendor space or accessibility can be sent to [email protected], and u-pick produce is available for an additional fee at the front gate. Bring a reusable shopping bag.

Trip highlights

Difficulty

easy.

Duration

7 hours.

Fitness level

Light walking across grassy fields; suitable for families with young children and strollers though some uneven ground exists.

Frequently asked questions

When is the festival held?

This one-day event is scheduled for Saturday, September 26th from 9:00 AM to 4:00 PM with check-in at Wesley Wells Farm.

Do I need to pay to pick pumpkins?

Yes—u-pick pumpkins, flowers, and vegetables are available for an additional fee paid at the front gate.

How do I apply as a vendor?

Vendor applicants must upload photos with their application or email them to [email protected]; applications are reviewed and payment is charged only after acceptance.

Is there parking?

On-site parking is typical for farm events; arrive early for the best spots and carpool if possible.

Are pets allowed?

Pet policies are not specified—contact the organizer at [email protected] to confirm before bringing animals.

Is the festival wheelchair or stroller accessible?

Much of the site is stroller-friendly grassy ground, but some areas are uneven. Contact the farm for specific accessibility needs prior to arrival.

Local insights

Wildlife

Eastern bluebird
White-tailed deer

History

This is the event's 5th annual Pumpkin Festival held at Wesley Wells Farm, recognized as the largest you-pick farm in St. Johns County.

Conservation

Visitors are asked to respect planted areas, pack out trash, and support vendors using minimal packaging to reduce festival waste.

About Wesley Wells Farm

Wesley Wells Farm is a farm venue in St. Augustine, Florida, hosting seasonal festivals, vendor markets, and educational farm visits. The farm’s public events include a vintage-themed Christmas Festival with food trucks, a handmade market, festive hay rides, live music, Santa appearances, and opportunities to meet farm animals. Wesley Wells Farm also hosts a monthly Homeschool Day program that offers guided tours, hands-on lessons tied to a rotating monthly theme, animal interactions, u-pick harvesting, and scenic hay rides. For fall programming, Wesley Wells Farm schedules a Pumpkin Festival vendor market on September 27, 2025, featuring handmade shopping, farm strolls, u-pick activities, and animal encounters. In spring, the farm presents a Sunflower & Tomato Festival vendor event on May 10, 2025, combining a kids zone, a salsa tasting contest, live music, u-pick flowers and vegetables, hay rides, food trucks, and a handmade market. Wesley Wells Farm provides vendor opportunities at multiple seasonal markets and welcomes community participation through vendor booths and family-focused activities. Information about specific event dates, vendor applications, and daily programming is provided through event listings. Wesley Wells Farm focuses on on-farm experiences such as u-pick harvests and hay rides that connect visitors to agricultural activities. All descriptions reflect event features and scheduled dates as listed for the farm’s public events and programs. Vendor participants include handmade artisans and local food vendors. Event programming is tailored for families, homeschool groups, and local visitors seeking seasonal activities and market shopping. Reservations and vendor information are available on event notices online.

Base locationSt. Augustine, Florida

Tours offered4+

Specialty

Adventure tips

Buy U-pick tokens at arrivalU-pick pumpkins, flowers, and vegetables require an additional fee collected at the front gate—purchase early to avoid lines.

Wear closed-toe shoesGround is grassy and uneven in places; sturdy shoes keep kids and adults comfortable while walking between fields and booths.

Bring cash for small vendorsSome makers and food trucks prefer cash—carry small bills to speed transactions and tip performers or servers.

Plan for sun and bugsMidday September sun can be strong and there may be mosquitoes near planted rows—use sunscreen and insect repellent.

Recommended gear

Comfortable walking shoes: Keeps you steady on grassy, sometimes uneven farm ground.
Sun protection (hat/sunscreen): Midday September sun can be strong during open-air festival hours.
Reusable shopping bag: Handy for carrying pumpkins, produce, and market purchases.
Small cash stash: Useful for vendors and food trucks that may prefer cash payments.