As the cooler weather of autumn starts to roll in, the areas surrounding the Grand Oaks Resort, Florida, come alive with many fall festivals, craft fairs, and seasonal events. Whether you’re a resident or a visitor, there’s no better time to explore the local culture, enjoy festive activities, and find unique treasures. Here’s a guide to some of the best fall events in the area.
Hometown Halloween
When: Oct 23 – 26, 2025
Where: Brownwood Paddock Square, The Villages, FL
One of the most anticipated events of the season is the Hometown Halloween! Costumes, trick or treating, and Spooky good times will be had at Brownwood Paddock Square for this annual event.
Spanish Springs Heritage Festival
When: Oct. 14, 2025
Where: La Hacienda Recreation Center, The Villages, FL
Celebrate cultures worldwide during The Heritage Festival at La Hacienda Recreation Center on October 14th from 10 am-2 pm. Enjoy free live entertainment from the Strolling Entertainment and resident performer groups. Pick up your Passport at the info booth for your chance to win a commemorative Heritage pin.
Ocala Arts Festival
When:
October 25 & 26, 2025
Where: Downtown Ocala, FL
Just a short drive from The Villages, the Ocala Arts Festival is one of the premier art events in the region. This juried festival showcases the works of talented artists from across the country. With over 150 booths, you’ll find a wide variety of fine art, including paintings, sculptures, photography, and more. The festival also features live entertainment, food vendors, and activities for kids, making it a perfect outing for the whole family.
Mount Dora Craft Fair
When: October 25-26, 2025
Where: Historic Downtown Mount Dora, FL
A bit further afield but well worth the trip, the Mount Dora Craft Fair is a beloved event that attracts visitors from all over Florida. Held in the charming historic downtown area of Mount Dora, this fair features over 400 exhibitors offering a stunning array of handmade crafts, jewelry, and artwork. The picturesque setting, combined with live music and gourmet food options, makes for a delightful fall outing.
Leesburg Trick or Treat on Main Street
When: October 25th, 2025, from 4 PM to 7 PM
Where: Main Street, Leesburg, FL
For a spooktacular time, head to the Leesburg Trick or Treat on Main Street Halloween Festival. This family-friendly event features a costume contest, trick-or-treating, face painting, live music, and plenty of fun activities for kids. Local vendors offer a variety of crafts and goodies, and the festive atmosphere is sure to get you in the Halloween spirit. 4 pm-7 pm.
Conclusion
Autumn around the Grand Oaks Resort is a time of celebration, creativity, and community. With so many fantastic festivals and craft fairs to choose from, there’s something for everyone to enjoy. Whether you’re looking for unique handmade items, festive entertainment, or simply a fun day out with family and friends, these events are sure to make your fall season memorable.
So mark your calendars, gather your loved ones, and get ready to experience the best of fall!
