Here’s the thing nobody tells you about living in Sarasota.
You stop thinking about it like a vacation destination pretty quickly. You stop saying “we should go to that festival” in a vague, someday kind of way. Instead, you start marking your calendar in January and planning your whole year around the events that make this city feel like home.
The Sarasota Jazz Festival goes on the calendar in March. The Medieval Fair goes on in November. The Sunday Drum Circle isn’t even on the calendar because it’s every week — it’s just part of the rhythm of life here.
I’ve been tracking Sarasota’s event season for years now, and 2026 is genuinely stacked. There’s something worth going to almost every month. Some of these events are known across the state. Some of them are the kind of thing only locals know to show up for. And some of them — the ones I look forward to most — are both.
This is the full guide. Month by month. Honest recommendations. Everything you need to know before you go.
A Quick Look at the Full Year
Before we dive into each event, here’s the whole calendar at a glance:
| Month | Highlights |
|---|---|
| January | St. Armands Circle Art Festival, MLK Unity Walk |
| February | Thunder by the Bay, Shell & Marine Life Festival, Valentine’s at the Beach |
| March | Sarasota Jazz Festival, Sarasota Festival of the Arts, County Fair |
| April | Sarasota Film Festival |
| May | Gulfcoast Pride Fest, SiestaCon |
| June–August | Summer arts, theatre, trivia nights, Drum Circles |
| September–October | Sarasota Chalk Festival |
| November | Sarasota Medieval Fair, Siesta Key Crystal Classic, Fall Fine Art Festival |
| December | Medieval Fair continues, holiday season, MOD Weekend |
| Every Saturday | Sarasota Farmers Market (year-round) |
| Every Sunday | Siesta Key Drum Circle at sunset (year-round) |
| Every Wednesday | Nokomis Beach Drum Circle at sunset (year-round) |
Now let’s get into the good stuff.
January 2026
St. Armands Circle Art Festival — January 24–25
Where: 1 St. Armands Circle, Lido Key Hours: 10 AM–5 PM both days Cost: Free admission
I look forward to this one every single January. The 23rd Annual St. Armands Circle Art Festival takes one of the most beautiful outdoor shopping circles in Florida and turns it into an open-air gallery for the weekend.
Over 200 national and local artists display their work in gallery-style booths featuring life-sized sculptures, fine jewelry, paintings, glasswork, ceramics, and hand-crafted décor. The quality is genuinely high — this is not a beach craft fair. It’s consistently ranked as one of the best art festivals in the US.
What I love about this one is the combination of the setting and the scale. St. Armands Circle is already beautiful. Add 200 artists doing their best work, and you’ve got a weekend morning that feels genuinely special. Bring cash for anything that catches your eye. Something always does.
My tip: Go Saturday morning before the lunch crowd arrives. Grab coffee at one of the nearby cafés, walk the circle at your own pace, and stay for lunch at Speaks Clam Bar or Columbia Restaurant. That’s a perfect January Saturday in Sarasota.
MLK Unity Walk — January 19
Where: Robert L. Taylor Community Complex to Dr. Martin Luther King Jr. Park, 1845 34th St. Cost: Free
Sarasota’s community honors Dr. Martin Luther King Jr. with this annual memorial walk involving local schools and organizations. Leaders of different faiths come together for one of the year’s most meaningful mornings. Worth knowing about and worth showing up for.
February 2026
Thunder by the Bay — February 13–15
Where: Sarasota Fairgrounds, 3000 Ringling Blvd Hours: Friday 5–10 PM | Saturday Noon–10 PM | Sunday Noon–5 PM Cost: Tickets required (children 12 and under free)
I’ll be honest — I didn’t think Thunder by the Bay was my kind of event the first year I went. Motorcycle rally. Rock music. Lots of leather. Not my usual Saturday morning.
Then I went. And I stayed until they turned the lights off.
The 28th Annual Thunder by the Bay brings rock music and motorcycle culture together for an electrifying weekend. The 2026 headliners are Night Ranger, 38 Special, and Montgomery Gentry — and all headliner performances are included with your general admission ticket. There are also meet-and-greet sessions with Paul Teutul Jr. from American Chopper throughout the weekend.
But here’s the part that actually moved me: this Sarasota motorcycle rally has raised over $3.3 million for children and adults with special needs since it started 28 years ago. Every ticket sold, every vendor booth rented, goes to Suncoast Charities for Children. You’re having the time of your life and doing real good at the same time. That combination is hard to resist.
Beyond the music: custom bike and car shows, freestyle motocross stunts, a biker rodeo, charity rides, food, vendors, and on-site camping. Saturday night, when 38 Special hits the stage, is one of those Sarasota experiences that stays with you.
My tip: Book tickets through the official site at ShowSlinger — third-party sites charge significantly more. Saturday is the best single day if you’re only going for one.
Sarasota Shell Show and Marine Life Festival — February 13–15
Where: Sarasota Fairgrounds, 600 N. Beneva Road Cost: Admission (free bag of shells included)
This one runs the same weekend as Thunder by the Bay, which sounds chaotic but works surprisingly well — they’re at adjacent venues. The expanded 2026 event features exotic, rare, and common shells, rocks and minerals, jewelry, shell crafts, and coastal-inspired prizes. New participants this year include Turtle Watch, Bay Watch, Tampa Bay Fossil Club, and New College’s Marine Biology Department.
If you’ve ever spent a morning on Sarasota’s beaches and found yourself completely unable to stop picking up shells, this event is genuinely your people.
Valentine’s Day at the Beach — February 14
Where: Siesta Key Beach Pavilion Cost: Reservation required
Every Valentine’s Day, couples gather at Siesta Key Beach to renew their vows in a group ceremony at the pavilion. It’s one of those completely Sarasota things — warm air, Gulf water, Spanish moss and romance and a crowd of people choosing this beach to mark something important. Call ahead to reserve your spot.
March 2026
Sarasota Jazz Festival (46th Annual) — March 9–14
Where: Sarasota Municipal Auditorium, 801 N. Tamiami Trail Cost: Tickets from $67.30+ per day | All week VIP passes available Info: jazzclubsarasota.org
This is the crown jewel of Sarasota’s event calendar. Forty-six years old. Grammy Award-winning performers. A week of concerts that draws jazz lovers from across the country to a city that already has enough reasons to visit.
The 46th Annual Sarasota Jazz Festival returns March 9-14, 2026, presented by the Jazz Club of Sarasota. This year’s festival features legends such as Sammy Figueroa, Terell Stafford, John Pizzarelli, and Arturo Sandoval.
Here’s the week:
- March 9: Monday Night Jazz Cabaret with Danny Sinoff
- March 10: Jazz Trolley Pub Crawl through downtown Sarasota
- March 12: Terell Stafford Quintet + Florida All-State High School Jazz Band
- March 13: John Pizzarelli Trio + Sammy Figueroa
- March 14: Arturo Sandoval Band + Michael Ross & the SRQ All Star Band
The Jazz Trolley Pub Crawl on March 10 is my personal favorite event of the whole week. You hop a vintage-style trolley, bounce between downtown Sarasota’s best bars and restaurants, and live jazz follows you the whole way. It’s chaotic and wonderful and a little bit magical.
My tip: Buy tickets as soon as they go on sale — the best seats for Arturo Sandoval go fast. If budget is a concern, some outdoor and community events during the festival week are free. Check the Jazz Club of Sarasota website for the full schedule.
Sarasota Festival of the Arts — February 28–March 1
Where: J.D. Hamel Park, 199 Bayfront Dr, Sarasota Hours: 10 AM–5 PM Saturday and Sunday Cost: Free admission
The Sarasota Festival of the Arts showcases original works of artisans and crafters from across Florida and the United States. With over 70 artisans presenting their creations, the park transforms into an outdoor gallery featuring spectacular paintings, sculptures, jewelry, photography, glass, ceramics, fiber and wearable art, mixed-media, metalwork, graphics, woodworking, and more.
Free. Bayfront. Seventy-plus artists. A warm late-February weekend. This is one of those events that reminds me why I live here. Bring a tote bag and your credit card — you’ll find something you need to take home.
Sarasota County Fair — March
Where: Sarasota Fairgrounds Hours: Friday 5–11 PM | Saturday Noon–11 PM | Sunday Noon–10 PM | Monday–Thursday 4–10 PM Cost: Admission for rides and grounds
The county fair is ten days of rides, livestock shows, agricultural exhibits, midway games, live entertainment, and — the non-negotiable — funnel cake. Kids love the animal competitions. Adults love the local craft vendors. Everyone loves the fair food. It’s a classic Florida event that feels completely different from everything else on this calendar, and that’s exactly why I go every year.
Ringling Wine and Roses — March
Where: The Ringling Museum, 5401 Bay Shore Rd. Cost: Tickets (available January 2026) Attire: Floral-inspired cocktail
A champagne reception, multi-course dinner expertly paired with fine wines, and live music under the stars at one of the most stunning museum grounds in Florida. Proceeds support the John and Mable Ringling Museum of Art.
This is a date night event — the kind where you dress up properly, you arrive early to walk the grounds while the light is still good, and you stay until the music ends. The Ringling at night under the stars is genuinely extraordinary. Floral cocktail attire is requested, which is a rare and wonderful dress code.
For exactly what to wear to an evening like this, the what to wear in Sarasota guide covers the full range of Sarasota evening events — from casual dinners to special-occasion dressing.
April 2026
Sarasota Film Festival
Where: Various venues across downtown Sarasota Cost: Tickets per film; festival passes available
The Sarasota Film Festival is one of Florida’s most respected independent film events. The 2026 festival celebrated another successful year — the next edition is scheduled for April 9-18, 2027. For 2026, the festival brought independent films, documentaries, and narrative features to venues across downtown Sarasota over ten days.
If you’re a film person and you’re visiting Sarasota in April, this is your tribe. The venues are all walkable from each other, which means you can see two films in a day and have a great dinner between them at one of the best Sarasota restaurants along the way.
May 2026
Gulfcoast Pride — Be Fabulous Music & Arts Pride Fest — May 9
Where: Selby Five Points Park, Downtown Sarasota Hours: 3 PM onward Cost: Free
The Gulfcoast Pride Festival takes over downtown Sarasota with music, food, and family fun — a celebration of love and being your authentic self. The 2026 festival includes live music, local art, food vendors, and community in one of the most beautiful public parks in the city. Free to attend and genuinely one of the warmest, most welcoming community events of the year.
SiestaCon — May 9
Where: Robarts Arena, 3000 Ringling Blvd. Cost: Admission required
Sarasota’s locally run comic con returns for its third year. Panels, cosplay, vendors, and the specific joy of a convention that feels community-built rather than corporate. If you have comic book fans, gamers, or pop culture enthusiasts in your group — or if you just love a great cosplay crowd — SiestaCon is an excellent afternoon.
June, July & August 2026: Summer in Sarasota
Let me be honest about Sarasota’s summer event season: it’s quieter than winter and spring. Most of the big annual festivals happen during peak season when the weather is most comfortable for outdoor events.
But summer in Sarasota is not empty — and the people who live here actually love it.
What’s happening this summer:
Sarasota Contemporary Dance runs July 24 through August 17, 2026 — a summer performance series that brings contemporary dance to one of the best small-scale arts venues in the city.
Westcoast Black Theatre Troupe’s “Marvin: A Marvin Gaye Revue” runs July 24–26, 2026 — one of Florida’s best Black theatre companies bringing a tribute to Marvin Gaye’s iconic catalog.
Gecko’s Grill & Pub 24th Annual Trivia Tournament runs July 24 through August 8 — a beloved Sarasota summer institution. If you love trivia and want to feel like a local for a night, this is your event. The best Sarasota restaurants guide covers Gecko’s in detail.
Payne Park “SWING” Sculpture Dedication — July 30. The City of Sarasota dedicates “SWING,” a dynamic new sculpture by artist Michael DiCarlo celebrating movement, color, and the spirit of play at Payne Park Tennis Center, 2050 Adams Lane. Free, public, and a genuinely beautiful addition to the city’s public art collection.
The Year-Round Summer Anchor: Every Sunday at sunset, the Siesta Key Drum Circle happens — rain or shine, peak season or off-season, hurricane swell or flat Gulf. It’s the most consistent event on the Sarasota calendar and one of the best free experiences in Florida. I never get tired of it.
And if summer in Sarasota is on your radar, the what to wear in Florida in summer guide is genuinely worth reading before you pack — summer dressing here has its own logic.
September & October 2026
Sarasota Chalk Festival — Fall
Where: Downtown Sarasota streets Cost: Free to watch
The Sarasota Chalk Festival transforms streets into 3D works of art. World-class street artists fly in from around the globe to create massive chalk paintings — sometimes hundreds of feet long — on Sarasota’s downtown streets. The 3D pieces in particular are the ones that stop you cold: images so precisely drawn that they look like real holes in the ground or objects floating in space.
You can watch the artists work throughout the festival, which is one of the most interesting things about it. Day one looks like a sketch. Day three looks like something from a museum. And then it rains, or it dries out and fades, and it’s gone. The art is entirely temporary, which makes seeing it feel somehow more urgent and more beautiful.
This is hands-down one of my favorite events of the entire Sarasota year. Free. Outdoors. Extraordinary. Don’t miss it.
November 2026
Sarasota Medieval Fair — November 7 through December 6
Where: Woods of Mallaranny at Mallaranny Farms (permanent home). When: Every Saturday and Sunday, Nov 7–Dec 6, 2026.
Join us Saturdays and Sundays, November 7 through December 6, 2026. Step back in time and watch full-contact jousting, human combat chess matches, and other fantastic shows on 14 stages. Enjoy rides and play games.
Five weekends. Full-contact jousting. Fourteen stages of entertainment. People in extraordinary period costumes who will absolutely stay in character when you talk to them. Turkey legs the size of your forearm.
The Sarasota Medieval Fair has its permanent home in a genuinely beautiful wooded setting — the trees and natural landscape add something that a fairground location can’t replicate. It’s immersive in a way that sounds like it shouldn’t work and absolutely does.
I take everyone who visits me in November here. Without exception. It’s one of those events that works for everyone: kids, couples, groups, solo visitors. There’s no wrong way to do the Medieval Fair.
My tip: Go on a weekend afternoon rather than opening day — the costumes get more elaborate, and the performers hit their stride as the run continues. Bring cash for the food vendors (the turkey leg is not optional).
Siesta Key Crystal Classic — November
Where: Siesta Key Beach Cost: Free to watch
The Siesta Key Crystal Classic Master Sand Sculpting Competition brings jaw-dropping sand sculptures to the beach. Professional sand sculptors from around the world compete to create massive, intricate sculptures directly on Siesta Key’s famous white quartz sand. The scale and detail of these pieces are genuinely staggering — think 10-foot-tall figures, elaborate architectural details, and structural complexity that makes you stop and wonder how it’s physically possible.
It’s free to watch. It’s on one of the most beautiful beaches in America. And the sculptures are up for several days after the competition ends — check the exact dates so you can visit when they’re at their best.
Sarasota Fall Fine Art Festival — November
Where: St. Armands Circle, Lido Key
Drive over to St. Armands Circle on Lido Key to marvel at masterpieces during the Sarasota Fall Fine Art Festival. A second major art festival at the circle rounds out the year — similar in format to the January event, with fine art, jewelry, sculpture, and crafts from artists across the country displayed in the circle’s beautiful outdoor setting.
Ferraris on the Circle — November
Where: St. Armands Circle, Lido Key
High-performance cars on St. Armands Circle. Ferrari owners from across the region bring their vehicles to display — and in Sarasota, where the wealth tends to manifest quietly, this is one of the rare occasions where the collection is genuinely jaw-dropping. Free to attend and walk through.
December 2026
Sarasota Medieval Fair Continues — Through December 6
The Medieval Fair runs every Saturday and Sunday through the first weekend of December — making it the perfect holiday season event for families visiting during the Thanksgiving and early December window.
MOD Weekend — December
MOD Weekend invites visitors to take a deep dive into midcentury style on tours of architecturally stunning spots throughout Sarasota County. Sarasota has one of the most significant collections of mid-century modern architecture in the Southeast — the Sarasota School of Architecture produced buildings in the 1950s and 60s that are genuinely remarkable, and most of them are private homes you’d normally never see inside. MOD Weekend opens many of them up for guided tours.
If architecture, design history, or midcentury aesthetics are your thing, this is one of the most niche and genuinely rewarding events on the whole Sarasota calendar. Worth planning a December trip around.
The Events That Happen Every Single Week
These aren’t on the big festival calendar. They’re just part of Sarasota life. And they’re honestly some of my favorite things about living here.
The Sarasota Farmers Market — Every Saturday, Year-Round
Where: Lemon Avenue, Downtown Sarasota Hours: 7 AM – 1 PM Cost: Free to attend
The Saturday Farmers Market is the heartbeat of Sarasota’s community. Every week, local farmers, bakers, artists, coffee roasters, plant sellers, and food makers set up on Lemon Avenue downtown. It’s been running for over 40 years, and it’s genuinely excellent — not a tourist market, a real community market where locals do their weekly shopping.
My Saturday ritual: arrive at 7:30 AM for first pick of the good produce. Coffee from the roaster at the corner. Walk the whole market once before buying anything. Then circle back for everything I want.
For what to wear to a farmers market morning in Sarasota — and how to dress for the market-to-beach transition that happens naturally when you live here — the what to wear to a farmers market guide has the perfect outfits for every season.
The Siesta Key Sunday Drum Circle — Every Sunday at Sunset
Where: Siesta Key Beach (main pavilion area) Cost: Free
Every Sunday evening, people gather on Siesta Key Beach for a free community drum circle. It starts an hour or so before sunset — a few drummers, then more, then dancers, then fire spinners, then a crowd that fills the beach. When the sun actually hits the water, the drumming gets louder, and the whole thing becomes something much bigger than the sum of its parts.
I’ve been to this event too many times to count. It still gets me. Every time.
Show up 45 minutes before sunset. Bring a blanket or a chair. Bring cash for the performers and vendors. And bring someone, or come alone — both work completely.
The Nokomis Drum Circle — Every Wednesday at Sunset
Where: Nokomis Beach, Casey Key Road, Nokomis Cost: Free
The same concept as Siesta’s Sunday version, but smaller, more local, and far less crowded. This is the one the locals know about. If you want the drum circle experience without the full Sunday Siesta scene, Wednesday at Nokomis is the answer.
Practical Tips for Attending Sarasota Events
Plan around peak season (January–April). Most of Sarasota’s biggest events happen during peak season because the weather is perfect and the city is already full of visitors. If a specific festival is a priority for your trip, book accommodation early — peak season hotels and vacation rentals fill up months in advance.
Check parking before you go. Downtown events can make parking competitive. For events at the Sarasota Fairgrounds (Thunder by the Bay, the County Fair), parking is generally easy. For downtown and St. Armands events, arrive early or use rideshare to avoid the stress.
Dress for the event and the weather. Sarasota events span every dress code, from the absolute casual (Drum Circle, County Fair) to the genuinely formal (Ringling Wine and Roses). The what to wear in Sarasota guide covers every scenario — and if you’re attending a special event like the Ringling gala or a beach wedding nearby, the beach wedding outfit guide has the specific dress code guidance.
Combine events with beach time. Almost every event on this list is within 30 minutes of some of Sarasota’s best beaches. The best Sarasota beaches guide helps you pair the right beach with the right event day.
Bring kids. Sarasota’s event calendar is genuinely family-friendly. Thunder by the Bay (kids 12 and under free), the County Fair, the Medieval Fair, the Chalk Festival, the Crystal Classic — all of them are excellent for families. The best things to do in Sarasota with kids builds on this with a full guide to family activities year-round.
Planning Your Sarasota Trip Around the Events
If you’re visiting Sarasota specifically for an event, here’s how to think about the rest of your trip:
Visiting for the Jazz Festival (March 9–14)? Stay downtown or on Lido Key for easy access to the Municipal Auditorium. Make dinner reservations at Indigenous or Selva Grill before you arrive — these fill up during festival week. Visit the Sarasota Art Museum between sets.
Visiting for Thunder by the Bay (February 13–15)? Arrive Friday evening for the gates-open atmosphere and stay through Sunday. Sarasota Jungle Gardens makes an excellent Sunday morning activity before the afternoon session.
Visiting for the Medieval Fair (November–December)? The weather is perfect for beach time too — Siesta Key and Lido Beach are beautiful in November with smaller crowds than peak season.
Choosing between Sarasota and other Gulf Coast cities? The Sarasota vs. Naples guide and the Sarasota vs. Fort Myers comparison are both useful — Sarasota has a significantly richer events calendar than its neighbors, which is a real factor in the decision.
For accommodation: The Airbnb vs. hotel guide for Florida trips walks through the decision for different event types — for a festival weekend, a well-located hotel is often worth the extra cost for the convenience alone.
The Bottom Line
I’ve lived in Sarasota long enough to stop being surprised by how much this city offers throughout the year. But I haven’t lived here long enough to stop being delighted by it.
A Jazz Festival where Arturo Sandoval plays to a full auditorium in March. A drum circle that fills a beach every Sunday at sunset without anyone organizing it, year after year. A chalk festival that turns ordinary streets into something that makes you catch your breath. A Medieval Fair in a forest that runs for five weekends and somehow gets better every time you go.
This city knows how to have a good year.
Mark the calendar. Book the accommodation. Come for the event you planned. Stay for everything else you didn’t expect.
Want more Sarasota guides? From beaches to restaurants to what to pack, Belle on the Boardwalk has everything in one place.
