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The Best Annual Art and Music Festivals in Southwest Florida
In Southwest Florida, you get to enjoy waterfront art shows, downtown street festivals, student showcases, and live music weekends almost year-round. Not sure where to start? Below is a month-by-month guide to annual art and music festivals in Southwest Florida including Sarasota, Bradenton, and Parrish. (Tip: Dates can shift each year, so confirm details before you go!)
January: Sarasota Fine Art Festival
The Sarasota Fine Art Festival is a free annual event that turns Sarasota’s bayfront into an outdoor gallery. Expect paintings, sculpture, jewelry, photography, ceramics, and more from local, regional, and national artists. It’s also a great event for buyers who want to commission custom work directly from artists. Because admission is free, it’s an easy event to visit for an hour or make a full day of it. The open-air setting and artist access make it feel both elevated and approachable. Luckily, our residents of Aqua and Legends Bay are only about 20 miles away.
February: Downtown Sarasota Festival of the Arts
A longtime favorite on Main Street, Sarasota Festival of the Arts usually spans two days and multiple downtown blocks. You’ll see a wide range of fine art categories, meet artists in person, and enjoy a free, walkable outdoor experience. It’s a great excuse to spend a full day downtown, with plenty of nearby dining and coffee spots between gallery-style browsing. If you enjoy art with a lively city backdrop, this one delivers.
March: Manatee County Seafood & Music Festival
The Manatee County Seafood & Music Festival is a three-day annual festival that mixes live music, seafood vendors, arts/crafts, and family-friendly browsing. It’s an easy pick for people who want both food and music in one outing. The atmosphere is casual and social, so it works well for date nights, family plans, or meeting friends. Come hungry and plan to stay awhile, because there’s usually more to taste and hear than expected. Plus, it’s less than 10 minutes from our Aqua and Legends Bay communities.
March: BAM!Fest: Bradenton Art & Music Festival
Held along the Riverwalk, BAM!Fest is one of the area’s most immersive art-and-music events. You’ll find multiple stages, live visual art creation, pop-up performances, student talent, and interactive projects. It feels energetic and community-driven, with something happening at almost every turn along the waterfront. If you like festivals that are creative, active, and family-friendly, BAM!Fest is a standout. And when you live at Watercolor Place, you’ll only be about 10 miles from the fun.
June: Sarasota Music Festival
The annual Sarasota Music Festival is dedicated to classical/chamber music and is a standout for music lovers. It features high-level performances and a strong educational component through Sarasota Orchestra programming. Concert quality is consistently strong, and the programming often appeals to both longtime classical fans and newer listeners. It’s a great way to experience Sarasota’s arts scene in a more formal, performance-focused setting. And residents of our Aqua and Legends Bay communities are only about 10 miles away.
November: East2West Arts & Craft Market
The annual East2West Arts & Craft Market, led by the Parrish Arts Council, highlights local artists, student performers, family activities, and community fundraising. It’s a strong regional arts event for Parrish-area residents (like the ones in The Laurels, River Preserve Estates, and The Willows Medallion Home communities). The market’s community focus makes it feel especially meaningful, with proceeds supporting scholarships and local art programs. It’s also a great place to shop small before the holiday season ramps up.
November: Sarasota Living Arts Festival
The Sarasota Living Arts Festival is a newer but recurring multi-city festival that features visual arts, performances, family programming, and live music. It spans multiple locations and offers a broad snapshot of the region’s creative community. It’s a smart pick for people who like discovering newer events before they become crowded staples.
December: Bradenton Blues Festival
This annual downtown Bradenton Blues Festival is a signature for blues fans, held at the Riverwalk Event Pavilion near the Manatee River. It’s produced by Realize Bradenton and has become a seasonal tradition. The riverfront setting adds to the experience, especially with cooler December weather. If live blues is your thing, this is one of the area’s most reliable can’t-miss weekends — especially for those who live at Aqua and Legends Bay, which is only about 10 miles away.
Medallion Home: Enjoy Annual Art and Music Festivals in Southwest Florida
From winter art walks to spring Riverwalk performances and holiday blues weekends, Southwest Florida offers a festival calendar that keeps culture close to home. For buyers considering life in Sarasota, Bradenton, or Parrish, these annual events are part of what makes the lifestyle here feel vibrant, connected, and uniquely local. Contact us today to learn more or to schedule your tour.
