From October through May, there's an outdoor art festival in Sarasota almost every other weekend. White tents go up around St. Armands Circle, along the downtown bayfront at J.D. Hamel Park and down Main Street, and admission is almost always free. This calendar lists every 2026 to 2027 art and craft festival we could confirm on the organizers' own sites, with where each one happens and what to know before you go, so you can plan a winter trip around one or simply stumble into one on purpose.
Art Festivals at a Glance
- Season: mid-October through Memorial Day weekend, with the busiest stretch from January through March.
- Hours: most shows run Saturday and Sunday, 10 a.m. to 5 p.m.
- Cost: admission is free at every show listed here. You pay for parking and anything you buy.
- Three main settings: St. Armands Circle, J.D. Hamel Park on the downtown bayfront, and Main Street downtown.
- Who runs them: Paragon Festivals, Howard Alan Events (ArtFestival.com) and Hot Works, plus the St. Armands Circle Association, which promotes the shows on the Circle.
- Before you go: confirm the date on the organizer's website. Shows occasionally move for weather.
Fall 2026: October to December
- October 17 to 18: St. Armands Fall Festival of the Arts. Paragon's fall show on St. Armands Circle, with painting, sculpture, jewelry, glass, ceramics and more. See our full St. Armands Fall Festival of the Arts guide for parking and tips.
- October 17 to 18: Downtown Sarasota Craft Festival. ArtFestival.com lists this as the 30th anniversary edition. Last year's festival was at Selby Five Points Park, at Central Avenue and First Street, so check the 2026 location before you go.
- October 24 to 25: The Mall at UTC Art Festival with Craft Marketplace. An ArtFestival.com show at the University Town Center mall, east of I-75.
- October 31 to November 1: Sarasota Fine Art Show by Hot Works. J.D. Hamel Park, 199 Bayfront Drive, on Gulfstream Avenue.
- November 14 to 15: 37th Annual St. Armands Circle Art Festival. An ArtFestival.com show on the Circle, which the St. Armands Circle Association promotes as its Fall Art Festival and Sidewalk Sale.
- November 14 to 15: Sarasota Fall Fine Art Festival. Paragon, at J.D. Hamel Park on Bayfront Drive. With the St. Armands show the same weekend, you can see both in one trip.
- December 19 to 20: Sarasota Fine Art Show by Hot Works. J.D. Hamel Park again, a good weekend to shop for one-of-a-kind holiday gifts.
Winter 2027: January and February
This is peak season, when the most visitors are in town and the shows are at their liveliest. If you're flying in from the Northeast or Midwest for a winter break, odds are good there's a festival during your stay.
- January 2 to 3: Sarasota Fine Art Festival. Paragon, J.D. Hamel Park. A nice way to spend New Year's weekend.
- January 9 to 10: Sarasota Fine Art Show by Hot Works at St. Armands Circle. Hot Works moves to the Circle for this one, with the listed address 1 St. Armands Circle.
- January 30 to 31: 24th Annual St. Armands Circle Art Festival. ArtFestival.com's winter show on the Circle. In 2026, the city listed it as the Winter Art Festival and Sidewalk Sale, with national and local artists around St. Armands Circle Park.
- February 13 to 14: 39th Annual Downtown Sarasota Festival of the Arts. The big one downtown, on Presidents Day weekend. In 2026, the city listed more than 200 artists along Main Street from Orange Avenue east to Links Avenue, with leashed pets welcome. Proceeds benefit the Downtown Sarasota Alliance.
- February 27 to 28: Sarasota Festival of the Arts. Paragon, J.D. Hamel Park, Bayfront Drive.
Spring and Summer 2027
- March 6 to 7: Sarasota Fine Art Show by Hot Works. J.D. Hamel Park.
- March 20 to 21: 5th Annual Downtown Sarasota Fine Art and Craft Fair. ArtFestival.com. The 2026 edition was on Main Street at Orange Avenue.
- May 29 to 30: St. Armands Fine Art Festival. Paragon's Memorial Day weekend show at St. Armands Circle Park. Paragon notes a $5 fee at the St. Armands garage during the event.
- Early June: St. Armands Circle Craft Festival. Usually the first weekend of June. In 2026 it ran June 6 to 7. Check ArtFestival.com for 2027 dates.
- September: St. Armands Art Festival and Craft Marketplace. In 2026 it ran September 12 to 13. The 2027 date isn't posted yet.
Where the Festivals Happen
St. Armands Circle. Booths wrap around the Circle and its center park, with the regular shops and restaurants open behind them. Park in the city garage at 57 N. Adams Drive. On a normal day the first hour is free once you register your plate in the Passport app or at a pay station, and the city may charge a flat $5 rate during special events. Street meters run $1.50 an hour, 10 a.m. to 8 p.m., Monday through Saturday. Our St. Armands Circle guide covers the rest of the neighborhood.
J.D. Hamel Park. A small park on the downtown bayfront at 199 Bayfront Drive, where Gulfstream Avenue meets the water. It's an easy walk from downtown hotels and restaurants, and the bayfront views make it a pleasant place to browse.
Main Street. The downtown festivals close Main Street to traffic and line it with tents, so you can pop into the shops and cafes between booths.
Downtown and St. Armands are linked by the Ringling Bridge, and the free Bay Runner trolley connects downtown, St. Armands and Lido Beach. Check SarasotaBayRunner.com for current hours.
More Art Beyond the Booths
The Chalk Festival. The Sarasota Chalk Festival is not taking place in 2026, according to the Observer, but its permanent Avenue of Art sidewalk paintings in Burns Square are open to walk anytime. Our Chalk Festival guide has the details.
Living Arts Festival. From November 8 to 15, 2026, Sarasota Rising's Living Arts Festival brings special programming and performances to arts organizations around the region. It's more performances than tents, but a great week for an arts-focused trip.
Tips for Buying Art at an Outdoor Festival
- Go early. The first hour is the calmest time to talk with artists, and mornings are cooler.
- Walk the whole show first. It's easy to come back to the booth you can't stop thinking about.
- Ask about shipping. If you flew in, many artists can ship larger pieces home for you.
- Take a card. Many artists sell online too, so you can buy later once you've measured the wall.
- Dress for the sun. Even in January, a full afternoon on pavement can be bright and warm.
What to Bring to a Festival Day
Most of these shows are a long, sunny walk, so a few basics go a long way. Our shop is at 410 St. Armands Circle and open every day from 9 a.m. to 9 p.m., so you can grab what you need before a show on the Circle opens.
- Shade for your face. The Siesta Key Cap Rempa Sand or the Sarasota Cool Fit Visor keeps the sun off while you browse.
- Lip and skin protection. Sun Bum Lip Balm SPF 30 slips in a pocket. See more in sun care.
- A layer for winter mornings. January shows can start cool. The Longboat Key Mock Neck is easy to take off by noon.
- A souvenir of the islands. The Keys Tee has a map of the keys, a nice reminder of the season you spent here.
Frequently Asked Questions
When is art festival season in Sarasota?
Outdoor art festivals run from mid-October through Memorial Day weekend, with the most shows from January through March. A few St. Armands craft and art shows also happen in June and September.
Are Sarasota art festivals free?
Yes. Every show on this calendar has free admission. You pay only for parking and anything you buy.
When is the Sarasota Festival of the Arts in 2027?
Paragon's Sarasota Festival of the Arts is February 27 to 28, 2027, at J.D. Hamel Park on Bayfront Drive, 10 a.m. to 5 p.m. both days.
When is the Downtown Sarasota Festival of the Arts in 2027?
ArtFestival.com lists the 39th annual Downtown Sarasota Festival of the Arts for February 13 to 14, 2027. In 2026 it filled Main Street from Orange Avenue to Links Avenue.
When are the art festivals on St. Armands Circle?
Confirmed dates are October 17 to 18 and November 14 to 15, 2026, and January 9 to 10, January 30 to 31 and May 29 to 30, 2027. Check each organizer's site before you go.
What are the hours of Sarasota art festivals?
Most run Saturday and Sunday from 10 a.m. to 5 p.m. Confirm hours on the organizer's site for the show you plan to attend.
Where is J.D. Hamel Park?
On the downtown Sarasota bayfront at 199 Bayfront Drive, near Gulfstream Avenue. Paragon and Hot Works hold several shows there each season.
Where do I park for an art festival on St. Armands Circle?
Use the city garage at 57 N. Adams Drive. The city may charge a flat $5 rate during special events, and street meters cost $1.50 an hour from 10 a.m. to 8 p.m. Monday through Saturday.
Are dogs allowed at Sarasota art festivals?
It depends on the show. The city's listing for the Downtown Sarasota Festival of the Arts welcomes leashed pets, but check each organizer's rules before bringing a dog.
Is there a Sarasota Chalk Festival in 2026?
No. The Observer reported in June 2026 that the festival is not taking place this year. The Avenue of Art sidewalk paintings in Burns Square are still there to see.
Who organizes the Sarasota art festivals?
Most are produced by Paragon Festivals, Howard Alan Events (ArtFestival.com) and Hot Works. The St. Armands Circle Association promotes the shows on the Circle.
Plan Your Art Weekend
Pick a show, book your stay, and leave room for the beach. If your festival is on St. Armands Circle, stop by and see us at 410 St. Armands Circle. We're happy to point you to the garage, the restrooms or the best way to Lido Beach. Can't wait for your trip? You can shop the Keys online anytime.