The call: Put Sweet Season Farms’ Corn Maze & Fall Fun Festival in Milton on your calendar first—it’s the closest true fall-festival day out, and it starts in two weeks.

Real-time local factors

• Sept. 26–Nov. 8, 2026: Saturdays 9 a.m.–5 p.m.; Sundays 11 a.m.–5 p.m. at 2260 Horn Rd., Milton. Tickets/details
• It has the full farm setup: corn maze, hayride, pumpkins, kid attractions, food, and photo spots.
• Gate admission listed for 2026: $18.50 + tax for the all-attractions “Whole Cob”; ages 2 and under free. Free parking.
• Friday-night flashlight-maze dates are Oct. 23 and Oct. 30, 6–10 p.m.—better for older kids/teens or a date night.
• Because it is outdoors, check weather/operating updates before driving out; the farm is generally not open to the public weekdays.

Runners-up

• Perfect Plain Oktoberfest — downtown Pensacola, Sept. 26, 11 a.m.–8 p.m. Go here instead if you mean a beer-and-food festival rather than a family farm day.
• Breeze-O-Ween — Gulf Breeze, Oct. 11, 5–8 p.m. Better if you want a shorter, kid-focused Halloween outing.
• Panzik Acres Fall Market on the Farm — Nov. 21, 11 a.m.–4 p.m. Better if you want vendors and a farm market rather than rides/maze attractions.

What flips this: If you specifically mean a strawberry festival, those are usually spring events—not something I’d wait for this fall; Sweet Season is the best nearby equivalent right now.

For more smaller Pace/Milton pop-ups, keep an eye on the Visit Pensacola calendar—Santa Rosa County events can get posted closer to the date.

👉 Are you looking for something mainly for little kids, or more of a food/beer-and-vendors kind of festival?