October in Southwest Florida is a magic month. The heat softens. The humidity eases. The sky feels clearer. Whether you live here year-round or are visiting as a seasonal resident (or even just weekend curious), October offers a rare sweet spot: great weather, fewer crowds, and a calendar full of events across Sarasota and Manatee counties.
Related Article: HALLOWEEN FUN FOR FAMILIES IN SOUTHWEST FLORIDA
In this guide, I’ll walk you through the very best happenings — from family carnivals and cultural festivals to spooky fun and nature walks. I’ll give you dates, times, insider tips, and how to plan your weekends so you don’t miss out. Let’s dive in.
So, if you sit down at the start of the month to map out which weekends to block off, this list will help you pick your priorities (or better yet, attend them all).
To make it easier, I’ve grouped events by theme (arts & culture, family & festivals, seasonal/Halloween, nature & outdoors) and then listed a handful of local “hubs” (Sarasota area, Venice, Bradenton/Manatee County) so you see what’s nearby. For each event, I include:
Before we jump in, one caveat: event details may shift (times, pricing, even cancellation). Always double-check the official event website or local listings.
When: October 20, 2025, 6:00 pm (and continuing monthly through April)
Where: Bayfront Gardens, Bolger Campiello, Sarasota (on the waterfront)
Cost / Admission: $25 for general admission / $20 for members (with limits)
What to Expect:
Tips:
When: October 4–5, 2025
Where: Burns Court Cinema, 99 Bottles, Fab LGBTQ Center, Sarasota
What to Expect: Independent films — narrative, documentary, short films — often with Q&A sessions, local filmmakers showcased.
Event Link
Tips:
When (October date): October 3, 2025
Where: Sarasota Opera House
What to Expect: A showing of Beetlejuice (1988) on the big screen, complete with ambiance and likely costume components.
Event Link
Tips:
When: October 24–25, 2025
Where: Van Wezel Performing Arts Hall
What to Expect: The orchestra performs the legendary soundtrack while the movie plays — a sensory delight for movie buffs and music lovers alike.
Event Links
Tips:
When: Oct 31 – Nov 2, 2025
Where: The Mall at UTC, Sarasota
What to Expect: Carnival rides, food trucks, community performances, trunk-or-treat — fun for all ages. The organizers expect thousands of attendees.
Event Link
Tips:
When: October 25, 2025
Where: The Bazaar on Apricot and Lime, Sarasota
What to Expect: Trick-or-treating, themed vendor booths, possibly costume contests, family-friendly Halloween fun.
Event Link
Tips:
When: October 17 onward (3-day festival)
Where: Downtown Sarasota
What to Expect: Live music, beer gardens, local vendors, food trucks; a fall party feel in an urban setting.
Event Link
Tips:
When: Fridays in October (weekly)
Where: The Teal Turtle Boutique area (Bradenton)
What to Expect: Rotating lineup of food trucks, casual dining outdoors, community atmosphere.
Event Link
Tips:
When: Multiple dates in October
Where: Lakewood Ranch Main Street / Waterside Place
What to Expect: Blocks party concerts, artisan markets, themed events (Pumpkins & Pajamas, Kids’ Night Out).
Event Link
Tips:
October is also a great month to reconnect with nature. Below are some free or low-cost opportunities:
Sarasota County’s Parks & Rec department runs a series of Ecowalk programs through local preserves:
Plot events in Sarasota, Venice, Bradenton on a simple map (or mental map). Try to cluster events that fall on the same weekend or near one another so you can hit multiples in one trip.
Cultural events, theater, or any limited-capacity shows tend to sell out. Don’t wait until the last minute.
Events may shift, get postponed, or add ticket tiers. Always refer to the event’s official page or local chamber listing one or two days before attending.
Many events are free or low cost (nature walks, markets). Save splurges for theater, dining, or high-tier performances.
If you go to a blockbuster event one day, balance the next day with a relaxed nature walk or local market so you don’t burn out.
October in Sarasota and Manatee counties is a hidden gem for event-seekers. It’s when the region wakes up after summer, when art and nature and creativity converge.
If I were you, I’d block off a few weekends now, pick “must-do” events, and leave a little breathing room for surprises. And don’t forget — check event pages again the week of, because nothing is more disappointing than driving across town only to find times changed.