The Villages October Fall Favorites: Local Guide for 2026

Fall in Central Florida means warm days, cool nights, and a full calendar of local favorites right around The Villages. From town square festivals to classic corn mazes, this is your 2026 October guide, curated by Lili Whittington, Broker Associate at Soundings LLC, serving Marion, Sumter, and Lake counties for 20+ years.

On the Town Squares

The squares are where October really shows off in The Villages. Here is what is on the calendar this month.

• Arts & Crafts Festival at Spanish Springs, Oct 3-4, 10am-5pm: handmade crafts, artisan vendors, food trucks, and live entertainment on the Square.
• Halloween Across The Villages, Oct 31: themed Halloween festivities at Eastport, Brownwood, Spanish Springs, and Lake Sumter Landing.
• Seasonal sips all month: the Witch's Brew, Pumpkin Spike, Vampire's Kiss (at Spanish Springs on Halloween), and a Cranberry Mule mocktail.
• Live music: The Mudds Jazz & Blues Band at the Brownwood Paddock Square outdoor concert series, Oct 28 at noon. Plus shows at the Savannah Center and Sharon L. Morse Performing Arts Center all month (Oklahoma, Absolute Queen, Legacy Five, and Golden Girls: The Laughs Continue).

Pumpkin Patches & Corn Mazes

A short drive from The Villages, the farms of Mount Dora, DeLand, and the surrounding counties get into full fall swing. Some of the best patches and mazes of the season are right here.

• Fall in the Field at Renninger's, Mount Dora, Oct 3-4, 9am-4pm: free admission and parking, the Hite's Heirloom Pumpkins tradition, and a petting farm on Saturday. Located at 20651 US Highway 441.
• Harvest Fields Corn Maze & Hayride, DeLand: open Oct 3-25, Saturdays and Sundays 10am-6pm, plus a Haunted Hayride on Fridays and Saturdays 7-11pm from Oct 9-24. Tickets available online.
• Mayhem Ranch Fall Festival, Morriston (Marion County): a family favorite fall festival just north of The Villages.
• Southern Hill Farms, Clermont (Lake County): seasonal farm fun and pumpkins, a short drive into south Lake.

Festivals, Fairs & Big Events

Beyond the farms, October weekends bring some of the region's biggest festivals, from Leesburg to Mount Dora to historic Ocala.

• Leesburg Asian Food Festival, Oct 2-4.
• Mount Dora Bicycle Festival, Oct 10-11: more than 1,000 cyclists touring scenic rural Lake County roads.
• Ocala Arts Festival, Oct 25-26, 10am-5pm in Historic Downtown Ocala: free and open to the public, 150+ artists from across the country and local food vendors.
• Mount Dora Craft Fair, Oct 24-25: an eclectic mix of 400+ arts and crafts booths, a three-decade tradition.

Lili's Fall Tip

October is one of the loveliest months to see The Villages before you buy. Weekday visits are quieter, and you can catch a square concert and a farm stand in one afternoon. Whether you're relocating, downsizing, or just curious, I'd love to show you around.

Event details were verified at publish time; always confirm dates and hours before you go.