Fall Fun in St. Augustine: Festivals, Music & Local Happenings

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Fall has arrived in St. Augustine, Florida, and the season is bringing exciting events! Whether you’re searching for St. Johns County homes for sale or just looking for fun weekend plans, here’s what’s happening around town. 🍂

Fall Festivals & Events in St. Augustine FL | St. Johns County Homes for Sale🎃 Local Spotlight: Pumpkin Festival + Handmade Market

📍 Wesley Wells Farms | 2680 Ada Arnold Rd., St. Augustine, FL
📅 Saturday, Sept. 27, 2025 | 9:00am – 5:00pm
Enjoy u-pick pumpkins, fresh veggies, flower fields, farm animals, food trucks, live entertainment, and a handmade market. This family-friendly festival is the perfect kickoff to the fall season.


🎶 Events This Week in St. Augustine

Sing Out Loud Festival: Songwriters Festival
📍 Tringali Barn | Sept. 26–28 | Free


Lake Street Dive featuring St. Paul & The Broken Bones
📍 St. Augustine Amphitheatre | Sept. 27 | $66.97–$100.98


Estuary Fest 2025
📍 GTM Research Reserve, Ponte Vedra Beach | Sept. 27 | Free


Fall Festivals & Events in St. Augustine FL St. Augustine Record Fair
📍 St. Augustine Amphitheatre | Sept. 28 | Free


🏡 Thinking About Moving to St. Augustine?

From fall festivals to coastal charm, St. Augustine continues to prove why it’s one of the best places to live in Florida. Whether you’re searching for the best neighborhoods in St. Augustine FL, exploring Palm Coast real estate, or connecting with the best realtor in St. Augustine FL, our team is here to guide you every step of the way.

✨ Ready to find your dream home? Contact us to explore homes for sale in St. Augustine FL today and experience the lifestyle that makes this historic city so special.