Looking for the best things to do in Sarasota this weekend? This lineup has a little bit of everything — Mother’s Day at The Bay, Fiddler on the Roof at Asolo Rep, Sarasota Cars & Coffee at UTC, SiestaCon at Robarts Arena, youth rowing at Nathan Benderson Park, outdoor movies, guided kayaking, live music, farmers markets, and free events from The Bay to Lakewood Ranch.
Whether you want something easy and free, something family-friendly, something outdoors, or a simple way to celebrate Mom, these are the events actually worth your time around Sarasota and the surrounding towns.
And since this weekend includes Mother’s Day, happy Mother’s Day to all the moms, grandmothers, stepmoms, mother figures, and women who keep showing up for the people around them.
Honestly, mothers deserve to be celebrated every day of the year.
As someone who helps relocation buyers make the move here, I’m always reminding people that Sarasota living is about more than a house — it’s about how life actually feels once you’re here. Weekends like this are a good example.
See you out there. –Mike Payne
Quick Weekend Snapshot:
🙏 National Day of Prayer in Downtown Sarasota → Payne Park (Thursday, 5:00–6:00 p.m.)
🎸 UTC Live on The Green with NoFilter → The Green at UTC (Thursday, 6:30–9:30 p.m.)
🙏 Venice National Day of Prayer Outside Happening → Centennial Park, Downtown Venice (Thursday, 7:00–8:00 p.m.)
🎬 Cinema at The Bay: Fargo → The Bay Park (Thursday, 7:30–9:15 p.m.)
🎭 Fiddler on the Roof → Asolo Repertory Theatre (May 7–24)
🎥 Movie in the Park → Waterside Place, Lakewood Ranch (Friday, 7:00–9:00 p.m.)
🛶 Ride and Paddle at The Bay → The Bay Park (Friday & Saturday, 9:00–11:00 a.m.)
🥕 Farmers’ Market → Downtown Sarasota South Lemon Ave (Saturday, 7:00 a.m.–1:00 p.m.)
🚗 Sarasota Cars & Coffee → The Mall at UTC, Lot 5 (Saturday, 8:00–10:00 a.m.)
🚣 USRowing Southeast Youth Championships → Nathan Benderson Park (Saturday & Sunday, 8:00 a.m.–5:00 p.m.)
💪 UTC FIT with Crunch Fitness → The Green at UTC (Saturday, 9:30–10:30 a.m.)
🦸 Annual SiestaCon → Robarts Arena (Saturday, 10:00 a.m.–7:00 p.m.)
🎣 96th Sarasota Tarpon Tournament → Anna Maria to Stump Pass fishing boundaries (May 9–June 14)
🥕 Farmers’ Market at Lakewood Ranch → Waterside Place (Sunday, 10:00 a.m.–2:00 p.m.)
💐 Mother’s Day at The Bay featuring Big Night Out → The Bay Park (Sunday, 4:30–5:30 p.m.)
Don’t want to search for this every weekend?
I send this out every Thursday morning so you don’t have to think about it.
If You Only Do One Thing This Weekend…
Since Sunday is Mother’s Day, I’m not picking one festival, concert, market, or show as the top event this weekend.
Celebrate Mom in a way that feels like her.
The best event is Mom.
And it does not have to be expensive. Most moms are not looking for a perfectly planned production. They want to feel remembered, appreciated, and seen. For some, that might mean brunch at a favorite Sarasota restaurant. For others, it might be coffee, a walk at The Bay, a slow morning at the Farmers’ Market at Lakewood Ranch, a sunset on Lido, or an hour together with phones put away.
Choose something she would actually enjoy.
Not what looks good on Instagram.
Not what checks a box.
Not what everyone else is doing.
A handwritten note, a phone call, a visit, a beach walk, flowers, lunch, or simply time together can mean more than anything you buy.
So if you only do one thing this weekend, make it this:
Celebrate Mom in the way that matters most to her.
She deserves it on Mother’s Day — and honestly, every day of the year.
Top Picks This Weekend
🚣 2026 USRowing Southeast Youth Championships
Saturday, May 9 – Sunday, May 10 | 8:00 a.m. – 5:00 p.m.
Nathan Benderson Park
Spectator event
Nathan Benderson Park hosts the USRowing Southeast Youth Championships this weekend, bringing top youth crews from across the region to Sarasota. It is a major competition with national-qualifying implications, which gives the event more energy than a casual local regatta.
Even if you are not a rowing insider, Benderson is a great venue for spectators. It is one of those Sarasota-area events that makes it easy to get outside and watch something a little different.
🎭 Fiddler on the Roof
Thursday, May 7 – Sunday, May 24
Asolo Repertory Theatre
Ticketed
One of the most beloved musicals of all time makes its long-awaited debut on the Asolo Rep stage. Fiddler on the Roof brings music, humor, heart, family, tradition, and change together in a way that has connected with audiences for generations.
If you want one of the strongest arts picks of the weekend, this is it. It is the kind of show that works well for a date night, a Mother’s Day outing, or anyone looking for something a little more memorable than another casual night out.
🚗 Sarasota Cars & Coffee
🚗 Sarasota Cars & Coffee
Saturday, May 9 | 8:00 a.m. – 10:00 a.m.
The Mall at UTC, Lot 5
Free for spectators
Sarasota Cars & Coffee is one of the easiest and most consistently enjoyable Saturday morning events around. Expect hundreds of exotic, sports, import, and classic cars, plus complimentary coffee, a live DJ, and a fun crowd that makes this feel more like a social event than just a car show.
This month’s event also benefits The Haven, which gives it a little more meaning beyond the cars themselves. If you like lively but easygoing weekend events, this is a strong pick.
🦸 Annual SiestaCon
Saturday, May 9 | 10:00 a.m. – 7:00 p.m.
Robarts Arena, Sarasota
Ticketed
SiestaCon brings a full day of pop culture fun to Sarasota with celebrity guests, comic artists, voice actors, game artists, vendors, comics, toys, board games, video games, crafts, and more. It is one of the weekend’s best family-friendly indoor options, especially if you want something different from the usual beach or outdoor lineup.
For anyone into comics, fandoms, collectibles, or cosplay, this is one of the most distinctive events on the calendar this weekend.
🆓 Free Things to Do This Weekend
Looking for something to do without spending much? These are some of the best free events happening this weekend:
🙏 National Day of Prayer in Downtown Sarasota
🎸 UTC Live on The Green with NoFilter
🙏 Venice National Day of Prayer Outside Happening
🎬 Cinema at The Bay: Fargo
🎥 Movie in the Park
🛶 Ride and Paddle at The Bay Guided Tour (registration required)
🚗 Sarasota Cars & Coffee (free for spectators)
💪 UTC FIT with Crunch Fitness
🚣 USRowing Southeast Youth Championships (spectator event)
🥕 Sarasota Farmers Market
🥕 Farmers’ Market at Lakewood Ranch
💐 Mother’s Day at The Bay featuring Big Night Out (registration required)
🥕 Sarasota Farmers Market
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More Things to Do This Weekend
🎸 UTC Live on The Green with NoFilter
Thursday, May 7 | 6:30 p.m.–9:30 p.m.
The Green at UTC
Free
If you want an easy Thursday night out, this is one of the better free picks of the weekend. NoFilter brings a high-energy mix of danceable crowd favorites, and UTC gives you a convenient setting with restaurants nearby and plenty of room to relax.
Bring a chair or blanket if you want to settle in for the evening. It is a simple way to start the weekend early without overthinking it.
🙏 National Day of Prayer in Downtown Sarasota
Thursday, May 7 | 5:00 p.m.–6:00 p.m.
Payne Park, Sarasota
Free
This community gathering brings together local congregations and residents for an hour of prayer, reflection, and worship at Payne Park. It is a meaningful option for those who want something quieter and more community-centered to begin the weekend.
If that kind of event resonates with you, this is one of the more grounded and heartfelt gatherings on the calendar.
🙏 Venice National Day of Prayer Outside Happening
Thursday, May 7 | 7:00 p.m.–8:00 p.m.
Centennial Park, Downtown Venice
Free
If you are farther south or want a Venice option, this outdoor prayer event offers worship, music, speakers, and a community atmosphere in Centennial Park. Guests are encouraged to bring a chair and settle in for the hour.
It is a good fit for anyone who appreciates local events built around faith, reflection, and connection.
🎥 Movie in the Park
Friday, May 8 | 7:00 p.m.–9:00 p.m.
Waterside Place, Lakewood Ranch
Free
This is one of the easiest family-friendly Friday night plans around. Bring a blanket or lawn chairs, enjoy the outdoor movie setting, and let the kids burn off some energy with inflatables before the film starts.
With concessions available and a relaxed crowd, it is one of those simple events that works well when you want something low-cost and easy.
💪 UTC FIT with Crunch Fitness
Saturday, May 9 | 9:30 a.m.–10:30 a.m.
The Green at UTC
Free
If you want to balance the weekend fun with something active, UTC FIT is a solid option. This week’s outdoor workout is led by Crunch Fitness and includes music, movement, and an all-levels atmosphere.
Bring a mat, towel, and water, and expect a fun Saturday morning crowd. It is a nice way to do something healthy without making it feel like a chore.
🎣 96th Sarasota Tarpon Tournament
Saturday, May 9–Sunday, June 14
Fishing boundaries from Anna Maria to Stump Pass
$150 entry fee
This longtime local fishing tradition is one of the more distinctive events on the calendar. Serious anglers know it well, and even if you are not participating, it is a reminder of how tied Sarasota’s culture still is to the water.
If your crowd leans toward boating, fishing, or old-school Gulf Coast traditions, this one stands out.
🥕 Farmers’ Market at Lakewood Ranch
Sunday, May 10 | 10:00 a.m.–2:00 p.m.
Waterside Place, Lakewood Ranch
Free admission
This is a great Sunday option if you want a relaxed outing that still feels like an event. The market brings together local vendors, produce, flowers, baked goods, prepared foods, and plenty of reasons to stroll around Waterside Place.
It is also a strong Mother’s Day option if Mom would rather browse, snack, and enjoy an easy morning than deal with a packed restaurant.
Sarasota Weekend Picks That Also Show How the Area Really Lives
This weekend has a good mix of Mother’s Day plans, easy outdoor events, arts, family-friendly options, and a few bigger community gatherings.
You can keep it simple with Cinema at The Bay, Movie in the Park at Waterside Place, the Sarasota Farmers Market downtown, or the Farmers’ Market at Lakewood Ranch. You can make it more active with Ride and Paddle at The Bay, UTC FIT, or the USRowing Southeast Youth Championships at Nathan Benderson Park. And if you want something with more energy, Sarasota Cars & Coffee, SiestaCon, and UTC Live on The Green with NoFilter are some of the stronger picks of the weekend.
But this weekend, the real headline is Mother’s Day.
Whether that means brunch, flowers, a handwritten note, a phone call, a walk at The Bay, a trip to the farmers market, or just time together, I hope every mom gets celebrated in a way that feels meaningful to her. They deserve it Sunday — and honestly, every day of the year.
One thing I tell relocation buyers and sellers all the time: Sarasota is not just about what a property looks like online. It is about how the area lives day to day — where people gather, how far things really are, what the weekends feel like, and which parts of town match your pace. That is part of why weekends like this are useful.
Whether you are already local, thinking about a move, or preparing to sell and want to better understand what draws people here, weekends like this give you a clearer sense of the lifestyle behind the listings.
If you want to talk through Sarasota neighborhoods, buying, or selling, I’m always happy to help.
For more local events happening this weekend, check out Sarasota Lifestyle’s growing events calendar.
That’s your Sarasota weekend—whether you’re going out Friday night, exploring Saturday, or keeping it simple Sunday. Want this sent to you every Thursday? Join Sarasota Weekly here →
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