8 Must-See October Events in St. Augustine and a list of local pumpkin patches!
- meganbkling
- Oct 1, 2025
- 2 min read
October in St. Augustine is one of our favorite times of year. The air starts to cool just enough for outdoor festivals, farms open their gates for pumpkin season, and music fills the nights around town. Whether you’re looking for a family-friendly day in the corn maze, a night of blues under the stars, or a spooky Halloween market, there’s something happening every weekend. We’ve rounded up 8 can’t-miss events local pumpkin patches to help you plan your month.
1. The Maze at Sykes Family Farms / Crop Maze
When: October 4 – November 2, 2025 (weekends)This 9-acre farm maze is a fall favorite, with hayrides, pumpkin patches, farm animals, live music, games, and plenty of family-friendly “agritainment.” Perfect for kids and adults alike.More info: sycofarms.com
2. Pumpkin Festival & Handmade Market at Wesley Wells Farm
When: Saturday, September 27, 2025 (festival kick-off, with markets continuing into October) Celebrate the season with you-pick pumpkins, fresh produce, cut flowers, handmade goods, live entertainment, and food trucks. A fun way to support local artisans while getting your home decked out for fall.More info: wesleywellsfarm.com
3. Croctoberfest (Brew at the Zoo)
When: Saturday, October 4, 2025, 6:00 – 9:00 p.m.This 21+ event at the St. Augustine Alligator Farm pairs craft beer tastings with food trucks and live music, all set against the backdrop of the zoo after dark. More info: Alligator Farm Croctoberfest
4. Greek Festival
When: Saturday, October 11, and Sunday, October 12, 2025
St. Augustine's annual Greek Festival takes place at the Holy Trinity Greek Orthodox Church. For that weekend, the church grounds are transformed into a Greek neighborhood festival, featuring Greek music and dancing, a gift shop, food and drink to enjoy at the festival.
More info: Greek Festival
5. Halfway to SweetWater Music Festival
When: October 17 – 19, 2025Jam bands, rock, funk, soul, and psychedelic acts fill the stages at Colonial Oak Music Park for this three-day festival. A must for music lovers looking for a lively weekend downtown. More info: Roots Music Tickets
6. Vilano VIBE-Rations Music Festival
When: Saturday, October 18, 2025This beachfront music festival in Vilano Beach brings local bands, food, and family-friendly fun to the sand. A laid-back celebration of music and community right by the ocean.More info: vilanobeachfl.com
7. St. Benedict the Moor Blues Festival
When: October 24 – 26, 2025Three days of live blues music fill the air at St. Benedict the Moor Church in Lincolnville. With evening shows Friday and Saturday and a midday Sunday performance, it’s a cultural highlight that ties music to the city’s rich history.
More info: stbensbluesfest.com
8. Mad Monster Halloween Market
When: Saturday, October 18, 2025 This spooky marketplace blends Halloween fun with local vendors and entertainment. A seasonal event that’s perfect for shopping unique finds and soaking in October’s festive vibes.More info: Visit St. Augustine Festivals
Pumpkin Patches in St. Augustine
October in St. Augustine is full of ways to get outside and enjoy our community. Whether you’re looking for family-friendly traditions, live music, or a little spooky Halloween magic, there’s something happening almost every weekend. Save this list and share it with friends!
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