Welcome
Looking for things to do in Sarasota this weekend?
I have to start with something that caught me completely by surprise this morning: it actually felt cooler outside.
During our morning coffee, Barb and I opened up the house and let that refreshing late-September air come through. In Sarasota. In September. I wasn’t expecting that.
Now, I’m under no illusion that summer has packed its bags and left us for the year. This could very well be a Florida weather headfake, and by this afternoon we may be wondering what happened. But we’ll take it. After months of heat, humidity and afternoon thunderstorms, even a brief hint of what’s coming feels pretty good.
And the timing couldn’t be much better because there’s a lot worth getting outside for this weekend.
We’ve got the Casting for the Kids Coastal Classic & Family Festival at Phillippi Estate Park, the start of Oktoberfest at Edelweiss, a movie under the stars at UTC, Family Fest at the Van Wezel, the Venice Beach Party—and the Ski-A-Rees are back on the water for their first show of the fall season.
As always, I’m not trying to list everything happening around Sarasota. These are the events and experiences I think are most worth knowing about.
And this week, there’s one in particular I’d put at the top of the list.
⭐ Mike's Pick This Weekend
🎣 Casting for the Kids Coastal Classic & Family Festival
Saturday, September 26 | Noon–10 p.m.
Phillippi Estate Park | Sarasota
$5 Noon–6 p.m. | $20 after 6 p.m.
A Saturday afternoon in one of Sarasota’s prettiest waterfront parks would already make this worth considering. Add live music, food trucks, more than 30 vendors, raffles, fishing activities, a mullet toss and plenty for families to do, and you’ve got a pretty full day.
But what makes this one my pick isn’t really what’s happening at the festival.
It’s why they’re doing it.
Casting for the Kids provides financial assistance to local families dealing with pediatric cancer, helping parents spend less time worrying about bills and more time concentrating on their child.
The Family Festival is part of the organization’s larger Coastal Classic Fishing Tournament taking place September 24–27.
Saturday’s live music includes Audio Orchid, Ellipsis and Homegrown, with activities continuing throughout the afternoon and evening. Bring a chair and settle in for as much—or as little—of the day as you’d like.
Why I picked it: Sarasota has no shortage of festivals, concerts and things to do on a Saturday. I especially like the ones where simply showing up for a good time also helps someone else. This one brings the community together for families who could genuinely use the support.
⭐ Also Worth Your Weekend
🇩🇪 14th Annual Oktoberfest at Edelweiss
September 25–October 25
Edelweiss | 611 Manatee Avenue E., Bradenton
Free admission
You don’t have to squeeze Oktoberfest into one weekend at Edelweiss. Their 14th annual celebration stretches for an entire month with German food, beer and wine specials, live entertainment and plenty of Oktoberfest atmosphere.
Friday and Saturday hours are noon–9 p.m., and every Saturday includes a best-dressed contest—so apparently this is one occasion when breaking out the lederhosen really can pay off.
If you’d rather make Oktoberfest an evening out than attend a large festival, this is an easy option to keep in mind over the next several weekends.
🐉 Movies Under the Stars: How to Train Your Dragon
Friday, September 25 | Activities at 7 p.m. | Movie around 8 p.m.
The Green at UTC
Free
Bring the lawn chairs and blankets for another Friday night under the stars at UTC.
This month’s movie is the live-action How to Train Your Dragon, with the evening starting at 7 p.m. with face painting, concessions and special character visits before the movie begins after sunset around 8.
The Green is located near The Paper Store, and seating is limited. I’d arrive early, find a spot and grab dinner somewhere around UTC before the movie starts.
🌿 National Public Lands Day at Oscar Scherer State Park
Saturday, September 26 | 9 a.m.–Noon
Oscar Scherer State Park | Osprey
Free park entry for volunteers
Here’s something a little different for Saturday morning.
National Public Lands Day is an opportunity to spend a few hours helping take care of one of our area’s natural treasures.
Volunteers at Oscar Scherer State Park can help with projects including removing invasive plants, spreading mulch around playgrounds, picking up litter and maintaining trails.
Wear long pants and closed-toe shoes, and bring water and sunscreen.
It’s not exactly a traditional weekend event—which is one of the reasons I wanted to include it. Sometimes enjoying Sarasota also means helping take care of it.
🎭 Family Fest at the Van Wezel
Saturday, September 26 | 10 a.m.–2 p.m.
Van Wezel Performing Arts Hall | Sarasota
Free
The Van Wezel’s annual Family Fest returns with live performances, games, literacy activities, food trucks, a photo booth and plenty to keep younger families busy.
This year’s programming includes two sensory-friendly performances of Asolo Rep on Tour’s BEANSTALK: The Adventures of Jack and the Giant at 10 a.m. and 1 p.m., along with family-friendly improv from Florida Studio Theatre at 11:30.
Kids Market will also bring young entrepreneurs into the festivities with shopping and activities inspired by Jack and the Beanstalk.
It’s an easy Saturday-morning option, particularly for families with younger children.
🏖️ Venice Beach Party
Saturday, September 26 | 1–6 p.m.
Venice Beach | Venice
Free admission & parking
Live music, food trucks, cold drinks and an afternoon at the beach—that’s a pretty straightforward formula for a Saturday in Venice.
The Venice Beach Party runs from 1–6 p.m. with beer, wine and specialty drinks available and a free trolley running between Centennial Park and Venice Beach.
The event is rain or shine. Leave the coolers and pets at home.
And if that little taste of cooler weather sticks around through Saturday? Even better.
🌴 Local Weekend Favorite
⛷️ The Ski-A-Rees Are Back
Sunday, October 4 | 2 p.m.
Ski-A-Rees Stadium | 1602 Ken Thompson Parkway, Sarasota
Free
If you’ve lived around Sarasota for a while, chances are you’ve seen the Ski-A-Rees at least once. If you haven’t, this weekend is a good excuse to change that.
Sunday marks the first show of their 2026 fall season, with the team returning to the water at Ski-A-Rees Stadium on Ken Thompson Parkway.
Water skiers perform jumps, pyramids and other team routines right along Sarasota Bay—and the show is free.
There’s something wonderfully old-school Sarasota about spending a Sunday afternoon sitting beside the water watching a local water-ski team perform. It’s the kind of experience that doesn’t need to be reinvented every year.
Local tip: Get there a little early if you want a good viewing spot, and don’t forget the sunscreen. September may have teased us with cooler mornings, but that Florida sun hasn’t gone anywhere.
Planning More Time in Sarasota?
Finished planning this weekend? Here are some of Sarasota Lifestyle’s best local guides.
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Explore Sarasota
Start here for beaches, neighborhoods, restaurants, events, and local places worth knowing.
☀️ Sarasota Anytime
Not everything worth doing in Sarasota needs a special date on the calendar.
Summer is actually one of the best times to remember how many local activities happen week after week.
If nothing on this weekend’s event calendar grabs you, try one of these instead:
🥁 Drum Circles
There are opportunities around the area to catch one of Sarasota’s casual sunset drum circles—an easy way to combine a beach evening with something uniquely local.
🧘 Yoga on the Beach
Trade the studio for the Gulf. Recurring beach-yoga sessions offer an entirely different way to start—or sometimes finish—the day.
🏃 Summer Beach Runs
Summer running programs turn an ordinary trip to the beach into an evening activity, with the Gulf providing a pretty good reward at the finish.
🎭 Local Performing Arts
Florida Studio Theatre and Sarasota’s other performing-arts organizations don’t simply disappear when season ends. Summer can be a great time to catch a performance without the winter-season rush.
🌴 UTC Fun
Night markets, movies, live music and other recurring programming make UTC one of the easiest places to check when you’re looking for something casual to do.
🌴 Before You Go...
Maybe Fall Really Is Coming
I know better than to declare the arrival of fall in Sarasota because of one cool morning.
I’ve lived here since 1988. Florida weather has fooled me before.
But there was something awfully nice about opening the house during coffee this morning and feeling cooler air coming through instead of immediately reaching for the thermostat.
Those little seasonal changes are different here.
We don’t watch leaves turn brilliant shades of orange and red. We don’t pull sweaters out of the closet in September. And there’s a pretty good chance we’ll still have some 90-degree afternoons ahead of us.
Instead, fall tends to arrive in little hints.
A morning when the humidity isn’t quite as heavy. An evening when sitting outside suddenly feels comfortable again. The return of the Ski-A-Rees. More festivals appearing on the calendar. A weekend when being outdoors starts sounding like something you want to do rather than something you’re willing to endure.
Maybe this morning was just a headfake.
We’ll happily take it anyway.
See ya around town.
–Mike Payne
📅 Hosting an Event in Sarasota?
Have a festival, concert, community event, performance or other local experience you’d like considered for an upcoming edition of Sarasota Weekly?
Send me the event name, date and time, location, short description, admission information, website or ticket link, and a high-quality photo.
Thank you,
-Mike Payne
