Things to Do This May in Southwest Florida

Festivals, Concerts, Art Shows and Community Events Across Sarasota, North Port, Venice and Punta Gorda

May in Southwest Florida is one of those months that separates the tourists from the people who actually live here. The snowbirds have headed north, the beaches are quieter, restaurant wait times shrink, and the locals get to enjoy the best version of their own backyard. That is one of my favorite things about this time of year. You get all the beauty, all the waterfront sunsets, all the festivals, and about half the traffic.

I spend most of my weeks driving between communities across Sarasota County and Charlotte County, meeting buyers at homes in North Port, walking properties in Venice, showing waterfront in Punta Gorda, and grabbing coffee in downtown Sarasota. The upside of that schedule is I hear about events and gatherings that most people miss entirely. And May 2026 is loaded.

Whether you just moved here, you are visiting for the week, or you have been living in Southwest Florida for years and just need a reason to get out of the house, this is my complete roundup of the best things to do this May across our region.

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Punta Gorda: Festivals, Tacos and Waterfront Celebrations

Punta Gorda kicks off May with back-to-back events that make the first weekend one of the busiest of the entire month. If you have been thinking about exploring downtown Punta Gorda or spending a Saturday along the harbor, this is the weekend to do it.

Hibiscus Festival at Gilchrist Park | May 1, 2 and 3

The Hibiscus Festival is one of those events that feels uniquely Punta Gorda. It runs three days at Gilchrist Park along the waterfront, and it celebrates the city’s deep connection to the hibiscus flower and one of the world’s most well known hybridizers, a lifelong resident named Harry Goulding. Goulding grew roughly 60,000 varieties of hibiscus over his lifetime and won the American Hibiscus Society’s “Best in the World” category five times.

The festival features live music across two stages, plant vendors selling everything from tropical flowers to native landscaping, craft and art vendors, food trucks, a vintage car show, and the always entertaining Lil’ Miss Hibiscus Pageant. Friday evening kicks things off with live music starting around 6pm, Saturday runs from 9am to 4pm, and Sunday wraps up from 10am to 3pm. Admission is free.

Gilchrist Park itself is one of the most beautiful public parks in Charlotte County, sitting right on the water with views of the Peace River and Charlotte Harbor. If you have never been, the festival gives you a great excuse to experience it for the first time.

Punta Gorda Taco-Fest at Laishley Park | May 2

If you are someone who needs tacos, live music, and a cold beer on a Saturday afternoon, this one is for you. The annual Punta Gorda Taco-Fest takes over Laishley Park on May 2nd from noon to 6pm. The lineup includes Mexican and Latin food vendors, a full bar, beer stations, and live entertainment all day. This year’s headliners include the classic country group Pure Country, along with Marty and the Mosstones and an authentic mariachi band.

General admission is just $5 at the gate. VIP tickets are available and include covered seating near the stage, a dedicated VIP bar, complimentary beers, and private restrooms. Free parking is available at the Charlotte County Justice Center parking lot and throughout downtown Punta Gorda. Proceeds benefit the Florida Outdoor Education Foundation, a local nonprofit.

What I like about this event is the location. Laishley Park sits right on Charlotte Harbor. So even if you are not a huge festival person, the setting alone makes it worth showing up for a couple of hours. Bring chairs or a blanket if you are doing general admission.

Charlotte County History Talk | May 2

For anyone interested in learning more about the area’s past, Charlotte County Historian Dr. Jennifer Zoebelein hosts a history presentation at the Punta Gorda Library from noon to 3:30pm on May 2nd. This is one of those under-the-radar events that attracts a really engaged crowd. If you have recently relocated to Charlotte County and want to understand the region’s roots, this is a great starting point.

Visani Comedy and Tribute Shows | All Month

Visani Restaurant and Comedy Theater on Kings Highway in Port Charlotte continues to host nationally recognized comedians, tribute bands, and dinner shows throughout May. Steve Trevino performs on May 1st, and the schedule rotates with new acts weekly. It is one of the best dinner-and-a-show options in Charlotte County.

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North Port: Music, Running and Community Connection

North Port continues to grow its events calendar, and May has some genuinely fun options for families, fitness enthusiasts, and anyone who just wants to feel more connected to the community.

Newcomer Day | May 2

If you moved to North Port within the past year, or even the past five years, Newcomer Day is built for you. This free expo-style event runs from 10am to noon at the George Mullen Activity Center on Kramer Way. More than 40 community organizations, nonprofits, city departments, and local businesses set up tables to introduce residents to services, resources, parks, recreation programs, and volunteer opportunities.

I recommend this to every buyer I help relocate to North Port. Understanding the community beyond your front door makes a real difference in how quickly you feel at home. And it is completely free.

Wellen Park Country Music Festival | May 2

Downtown Wellen Park is quickly becoming one of the go-to entertainment hubs in the southern Sarasota County and northern Charlotte County corridor. The Country Music Festival runs from 4pm to 10pm at 19745 Wellen Park Blvd and features live country music, food vendors, shopping, and family-friendly activities.

If you have not visited Downtown Wellen Park yet, this is a great excuse to check it out. The area around the Grand Lake is beautifully designed, walkable, and built for exactly this kind of gathering. CoolToday Park (spring training home of the Atlanta Braves) is right next door, and the whole corridor has a resort-like energy that draws people from Venice, North Port, and Port Charlotte.

Fusion Fest 5K | May 9

Lace up your shoes for a good cause. The Fusion Fest 5K starts at 7:30am at the North Port City Center and supports the North Port Youth Soccer Club. There is also a 1-mile fun run and walk for families who want something a little more relaxed. Awards go out by age bracket, and registration is online only. Packet pickup is the evening before at Narramore Sports Complex.

Wellen Park Ongoing Events

Downtown Wellen Park runs events throughout the month that are easy to drop into. Their weekly lineup typically includes Saturday morning yoga on the Great Lawn, Monday morning Zumba, live music on Wednesday and Friday evenings, and the Wellen Park Night Market on the second Thursday of every month (May 14). The Night Market brings together independent artists, food vendors, home decor makers, and more from 6pm to 9pm. Dueling Pianos at Solis Hall happens the third Thursday (May 21) from 6pm to 10pm.

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Venice: Concerts, Symphony Under the Stars and Hurricane Prep

Venice in May has a personality all its own. The arts scene stays strong, the beach is stunning, and there are a couple of events that really stand out this month.

Tacos and Tequila Festival at CoolToday Park | May 2

CoolToday Park, the sprawling spring training facility off South West Villages Parkway, hosts a Tacos and Tequila Festival starting at 11am on May 2nd. Food, drinks, live music, and a party atmosphere in one of the best outdoor venues in the area. If you live in Venice, Wellen Park, or North Port, this is right in your backyard.

Lynyrd Skynyrd Tribute at Venice Community Center | May 23

For classic rock fans, the Venice Community Center hosts a Lynyrd Skynyrd tribute show on Saturday, May 23rd starting at 7pm. The Venice Community Center on Nokomis Avenue South has become a solid venue for tribute concerts and community events. Check the City of Venice events page for ticket details.

Venice Symphony: America’s Heroes Patriotic Pops Concert | May 23

This is one of the signature events of the season in Venice. Music Director Troy Quinn leads the Venice Symphony at CoolToday Park in a concert of great American music, including a performance by Liberty Voices, a world-renowned eight-part a cappella group specializing in Americana, folk, and patriotic songs. Gates open at 5:30pm, and the concert starts at 7:30pm. The evening wraps up with fireworks. This is a perfect Memorial Day weekend kickoff, and it draws people from across the entire region.

Bring a blanket, grab a spot on the lawn, and enjoy one of the best outdoor concert experiences in Southwest Florida.

Venice Farmers Market | Every Saturday

The Venice Farmers Market continues every Saturday morning at Venice City Hall. It has been running for more than 25 years, and it is one of the most consistent weekly community touchpoints in the city. Fresh produce, baked goods, local vendors, and a great excuse to spend a Saturday morning outdoors.

City of Venice Hurricane Expo | May 29

Hurricane season officially starts June 1st, and the City of Venice hosts its annual Hurricane Expo at the Venice Community Center on May 29th from 9am to 2pm. If you are a homeowner in Venice, North Port, Englewood, or anywhere in Sarasota County, this is a smart event to attend. You will learn about evacuation routes, home preparation, insurance considerations, and emergency resources. Living in Southwest Florida means being prepared, and this expo makes it easy to do that before the season starts.

 

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Sarasota: Art, Pop Culture and Waterfront Weekends

Sarasota in May is the cultural heartbeat of the region, and the event calendar reflects it. From fine art to comic books, from jazz to beach rugby, there is genuinely something for everyone.

Rock De Mayo Sarasota Block Party | May 5

Cinco de Mayo gets its own full-scale celebration in downtown Sarasota. The Rock De Mayo Block Party shuts down the streets for a day and night of tacos, tequila, cervezas, live music, and DJs. It is the kind of event where the energy builds as the afternoon rolls into evening. Bring a group of friends and plan to stay awhile.

SiestaCon at Robarts Arena | May 9

SiestaCon is Sarasota’s locally grown comic con, and it keeps getting bigger. This year the event returns to Robarts Arena at the Sarasota Fairgrounds from 10am to 7pm on May 9th. The guest lineup includes acclaimed comic creators Donny Cates and Ryan Stegman, voice actors Lisa Ortiz and John Gremillion, along with trading card game tournaments, cosplay contests, panels, creative workshops, and a massive vendor floor. General admission is $15, and kids 10 and under get in free.

If you have kids who are into comics, gaming, or cosplay, this is one of the best family-friendly pop culture events in the area. And honestly, plenty of adults go without kids and have a great time.

Sarasota County Fire Department Open House | May 17

The Sarasota County Fire Department hosts a free community open house at Station 4 on Old Bradenton Road from 9am to 1pm on May 17th. Families can meet firefighters, tour equipment, and take advantage of car seat safety inspections and bike helmet fittings. It is a fantastic, low-key Saturday activity for families with young children.

Sarasota Art Museum Events | May 19

The Sarasota Art Museum on the Ringling College campus hosts its monthly Uncorked wine tasting series on May 19th at 5:30pm, featuring six wines, gourmet cheeses, and a guided presentation. It is a refined, adult evening out, and the museum itself is worth the visit.

Behind the Curtain: Exploring the Van Wezel | May 18

Arts Advocates hosts a unique guided tour inside the Van Wezel Performing Arts Hall from 1:30 to 3pm. You will see artwork from the Arts Advocates collection by noted Florida artists, then step onto the stage for behind-the-scenes stories about the world of live performance. Tickets are $15 and benefit educational outreach programs.

Siesta Beach Rugby Tournament | May (Check Dates)

If you have ever wanted to see competitive rugby played on America’s number one beach, the Siesta Beach Rugby Tournament delivers exactly that. Teams battle it out on the sand during the day, followed by live music, DJs, food trucks, and the legendary Siesta Stumble bar crawl through Siesta Key Village. It is one of the more unique events on the entire Sarasota calendar.

St. Armands Fine Art Festival | May 23 and 24

The St. Armands Fine Art Festival transforms St. Armands Circle into an outdoor gallery of original artwork from across the country. Mediums include sculpture, jewelry, painting, photography, glass, ceramics, mixed media, metalwork, fiber art, and woodworking. The artists are on-site to discuss their work and accept commissions. Saturday and Sunday from 10am to 5pm, free admission. If you are visiting Sarasota for Memorial Day weekend, this is a must.

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Weekly and Ongoing Events Worth Knowing About

Some of the best things about living in Southwest Florida are not the big festivals. They are the consistent, weekly rhythms that make life here feel like something special.

Punta Gorda Downtown Farmers Market runs every Saturday morning from 8am to 1pm with ready-to-eat food, produce, art, souvenirs, and a crowd that feels like a neighborhood gathering.

Punta Gorda History Park Market is Sundays from 9am to 1pm, focused on antiques, art, original food products, and handmade goods.

Venice Farmers Market meets every Saturday at Venice City Hall, rain or shine, and has been running for over 25 years.

Englewood Farmers Market covers several blocks of Dearborn Street every Thursday through May, with just about everything you can imagine.

Downtown Wellen Park Live Music happens Wednesdays and Fridays, plus Saturday night concert series events. Free outdoor yoga is Saturdays at 9am and Zumba is Mondays at 9am.

Punta Gorda Chocolate and Wine Tasting is a weekly event that lets you sample vintages and craft beer in a relaxed setting. Check their schedule for May dates.

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Why Events Like These Matter When You Are Buying or Selling a Home

I write about events like these because they are a direct reflection of what it actually feels like to live in a community. When a buyer asks me what life is like in North Port or Venice or Punta Gorda, I do not just talk about home prices and school ratings. I talk about what your weekends look like. I talk about where you take your family on a Friday night. I talk about farmers markets and concerts and festivals that happen right down the street from the neighborhoods I help people buy and sell in.

That is what makes a place feel like home. Not just the house. The lifestyle that surrounds it.

If you are thinking about relocating to Southwest Florida, or if you already live here and are considering a move to a different community, I would love to help you figure out where you fit best. Sometimes the right neighborhood is the one with the right Saturday morning farmers market.

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Quick Reference: May 2026 SWFL Events Calendar

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FAQs: May Events in Southwest Florida

What are the best free events in Southwest Florida in May 2026? The Hibiscus Festival in Punta Gorda (May 1-3), Newcomer Day in North Port (May 2), the Venice Farmers Market (every Saturday), and the Sarasota County Fire Department Open House (May 17) are all completely free. The St. Armands Fine Art Festival (May 23-24) is also free admission.

What is there to do in Punta Gorda in May? Punta Gorda hosts the Hibiscus Festival at Gilchrist Park and the Taco-Fest at Laishley Park on the same weekend (May 1-3). The downtown farmers market runs every Saturday, the History Park Market runs every Sunday, and Visani in Port Charlotte has live comedy and tribute shows throughout the month.

What family friendly events are happening in Sarasota in May 2026? SiestaCon at Robarts Arena (May 9) is great for families with kids who enjoy comics and gaming. The Sarasota County Fire Department Open House (May 17) offers hands-on activities for young children. The St. Armands Fine Art Festival (May 23-24) is an easy, free outdoor family outing.

Are there any events at Wellen Park in May? Downtown Wellen Park hosts the Country Music Festival on May 2nd, the Night Market on May 14th, Dueling Pianos on May 21st, plus ongoing live music on Wednesdays and Fridays, Saturday morning yoga, and Monday morning Zumba.

When does hurricane season start in Florida? Hurricane season officially begins June 1st. The City of Venice hosts a Hurricane Expo on May 29th at the Venice Community Center from 9am to 2pm, which is an excellent way to prepare before the season begins.

What is there to do in Venice, Florida in May? Venice hosts a Tacos and Tequila Festival at CoolToday Park (May 2), a Lynyrd Skynyrd tribute concert (May 23), the Venice Symphony Patriotic Pops concert with fireworks (May 23), the weekly Saturday Farmers Market, and the Hurricane Expo (May 29).

What is there to do in North Port in May? North Port hosts Newcomer Day (May 2), the Fusion Fest 5K (May 9), and benefits from its proximity to Downtown Wellen Park’s full event calendar including the Country Music Festival, Night Market, and weekly entertainment programming.

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Cole Murray is a Realtor and team leader at Murray and Team | Keller Williams Island Life, serving buyers and sellers across Sarasota County and Charlotte County including North Port, Venice, Port Charlotte, Punta Gorda, Englewood, and surrounding communities.

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