60+ Memorable May Festivals in Florida

Are you looking for May Festivals in Florida? You’ve come to the right place. May is the perfect time to explore the many festivals that Florida has to offer!

At this time of year, the weather really begins to feel like summer with heat and humidity. South Florida’s rainy season begins, too, but it’s still a great time to enjoy the end of Florida’s festival season.

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Florida Arts Festivals in May

Art and craft festivals in Florida rank among the most popular festivals to attend. And May in Florida is the last time to attend an art festival before summer’s intense heat and afternoon rains. Art and craft festivals help to support local, regional, and emerging artists. Many of Florida’s art festivals are also recognized among the best in the country and are juried art shows.

1. ArtsQuest Fine Arts Festival

Held May 4-5 in Miramar Beach. This juried art show presents a great opportunity to discover new artists, whether new to the art world or just new to you. The two-day festival showcases more than 100 artists, many of which also sell their artwork. From ceramics to oil to photography, enjoy the art, mingle with artists, and snack on the food offerings.

2. 22nd Annual St. Armand’s Circle Art & Craft Festival

Held May 4-5 in Sarasota. This outdoor art and craft festival takes place on beautiful St. Armands Key near downtown Sarasota. St. Armand’s Circle is lined with upscale boutiques and cafes, towering palm trees, and lies just yards from the aquamarine waters of the Gulf of Mexico. Artists and vendors set up along the streets and invite visitors to peruse their wares and offerings.

3. Cocoa Village Summer Art and Craft Fair

Held May 11 in Cocoa. For decades, the historic Cocoa Village has brought artists and the public together in three annual art fairs. Hundreds of exhibitors and tens of thousands of visitors attend each year. Visitors enjoy strolling the quaint streets to browse the shops of the village as well as the vendors.

4. Mayfaire by the Lake

Held May 11-12 in Lakeland. One of the oldest art festivals in central Florida, Mayfaire by the Lake offers more than 140 artists a beautiful lakefront setting in which to display their art. For the past ten years, the long-running festival has been named one of the country’s “200 Best Art Shows” by Sunshine Artists Magazine.

5. Digital Graffiti Festival

Held May 17-18 in Alys Beach. Possibly one of the most unique festivals in Florida, this festival uses the white walls of buildings in north Florida’s Alys Beach as the canvas for visual artists. These architecture screens showcase videos, sound-motion-light shows, and more during the two day show. National Geographic called the Digital Graffiti Festival one of the “top 24 places in the world for unconventional art”.

6. 26th Annual Downtown Delray Beach Memorial Day Weekend Craft Festival

Held May 25-26 in Delray Beach. This free art and craft festival in South Florida is held outdoors at the Delray Beach Tennis Center. Artists, artisans, and crafters come from all over South Florida to show off their artwork and present their best for sale. Visitors can enjoy a variety of handmade goods.

Heritage Festivals

Florida boasts a rich history and heritage that spans hundreds of years and includes the stories of many unique pioneers. Heritage festivals in Florida are an important reminder of this history and culture.

These festivals celebrate the stories and culture of pioneers who settled in the area, as well as those who have made significant contributions to its development. Through a variety of activities, heritage festivals honor and recognize those who built up their communities, making them a great way to celebrate a town’s history and rich cultural heritage.

23. Belleview Founder’s Day Celebration

Held May 4 in Belleview. Belleview Founders Day is a family-friendly event which celebrates the founding of Belleview, a small town south of Ocala, back in the 1880s. At Founders Day, children enjoy activities such as games, crafts, and inflatables. For the rest of the family, there will be booths highlighting the city’s history as well as craft, business, and food vendors.

24. Howey Founders Day

Held May 4 in Howey-in-the-Hills. Held at Howey Mansion, the Howey-in-the-Hills Founders Day celebration features mansion tours, food trucks, and more than 40 art and crafts vendors. There will also be information about the town’s history and a vintage car show. Founded in 1925 as Town of Howey, the name was officially changed to Howey-in-the-Hills in 1927.

25. Drake’s Raid Re-enactment

Held May 10-11 in St. Augustine. In late May (possibly early June) 1586, 2000 British in 23 ships laid siege to San Agustín. Led by Sir Francis Drake, the town was captured and razed to the ground. The re-enactment commemorates this event and brings it to life. Enacters set up camp on Friday. On Saturday, the Oldest House Museum Complex will host a re-created 16th-century-style military encampment, featuring drills, weapons demonstrations and living history interpretations. The raid itself is re-enacted near the Orange Street redoubt in front of Ann O’Malley’s on Saturday evening.

26. Florida Folk Festival

May 24-26 in White Springs. This 71st annual festival is a celebration of the music, stories, and food that make Florida unique. Each year, the festival Folklife Area highlights a special topic of Florida heritage, and in 202 that’s earth. This festival features all aspects of Florida’s heritage, from Irish fiddlers to root beer floats. Learn about various traditions through exhibits and demonstrations, and enjoy the food that Florida loves.

Music Festivals in Florida

Music festivals offer the perfect opportunity to get together with friends and family, enjoy live music from your favorite bands, and have a day of fun. Whether you’re looking for an intimate gathering or a large event, music festivals are sure to be full of energy and excitement. Plus, you can find vendors selling amazing merchandise and delicious food trucks offering mouth-watering treats.

27. Key West Singers and Songwriters Festival

Held May 1-5 in Key West. The Key West Songwriters Festival brings five days of magical music and storytelling to Key West’s historic and quirky streets. The largest festival of its kind in the world, it’s known as a place where country bands and solo artists are launched into stardom, including the likes of Kacey Musgraves and Florida Georgia Line. Veteran songwriters engage in storytelling while lesser known acts put on the music. The 2024 lineup includes Cole Swindell, Dylan Marlowe, and Mackenzie Carpenter.

28. Sunfest

Held May 3-5 in West Palm Beach. Sunfest is a four-day waterfront music festival in West Palm Beach which features some of the country’s most well-known artists. In 2024, three stages will rock with acts such as Nelly, Billy Idol, and Dashboard Confessional. As with any multi-day music festival, expect to find art installations, vendors, and amazing food trucks.

29. Welcome to Rockville

Held May 9-12 in Daytona Beach. The Daytona International Speedway turns into an epic rock festival each May. This outdoor music festival features three stages, onsite campground, several bars, a Ferris wheel, a waterslide, and much more. The lineup for 2024 includes Slipknot, Limp Bizkit, Foo Fighters, and Mötley Crüe.

30. New Smyrna Beach Jazz Festival

Held May 17-19 in New Smyrna Beach. The New Smyrna Beach Jazz Festival is an annual event featuring live jazz performances from some of the best local and international artists. This year, the festival offers free admission on Friday and Saturday, so everyone can enjoy the amazing music. On Sunday, there will be special Jazz Brunches at various venues. It’s the perfect long weekend for jazz lovers of all ages!

31. As If! North Florida’s 90’s Fest

Held May 18 in St. Augustine. As If! North Florida’s 90’s Fest is here to make all your ’90s nostalgia dreams come true! The main attraction of the fest is undoubtedly the music, featuring performances by Deana Carter and Paula Cole. Jam out to iconic ’90s tunes or take a break at the selfie station, a slime zone, or enjoying the best ‘90s food from several food trucks. Go back in time for an unforgettable experience!

32. Jacksonville Jazz Festival

Held May 23-26 in Jacksonville. Jazz lovers rejoice! The Jacksonville Jazz Festival is back, filling the streets of downtown Jacksonville with an amazing collection of jazz performances. This year’s festival kicks off with the Jacksonville Jazz Piano Competition. The festival then continues with two stages featuring free, live performances from world-renowned jazz musicians and bands such as Joss Stone and Brian Culbertson. Come on down to Jacksonville and experience an unforgettable weekend filled with jazz!

33. Sunset Music Festival

CANCELLED IN 2024. Sunset Music Festival, one of the premier EDM festivals in Florida, has been on a rebranding journey through the end of 2023 and beginning of 2024, to include a new venue announcement. According to a Tampa Bay Times article, that venue is not yet ready so the festival has been cancelled in 2024.

34. Myakka River Blues Festival

Held May 27 in Venice. The Myakka River Blues Festival is one of the premier annual events in Venice, featuring some of the best blues musicians in the country. Since its inception in 2011, this festival has grown to become one of the most highly acclaimed events on Florida’s west coast. Taking place at Snook Haven Restaurant, this annual event celebrates the genre and its various styles with performances from renowned artists. There is something for everyone, from traditional blues to more modern interpretations. Attendees can enjoy a variety of food and drinks while listening to their favorite blues tunes.

35. Gulf Coast Jam Festival

Held May 30-June 2 in Panama City Beach. Get ready for four days of #countryonthecoast at the annual Gulf Coast Jam. This popular music festival in Florida’s panhandle features some of the top country music artists. In 2024, those include Morgan Wallen, Cody Johnson, and Jelly Roll. Gulf Coast Jam is also partnering with Jim Beam to present Welcome Sessions at Ms. Newby’s when finalists will perform for a spot to open on the Main Stage at the Festival.

Nature Festivals

Nature festivals are an amazing way to celebrate the beauty of the natural world. From science presentations and workshops to expos and other events, these festivals are a great way to explore and appreciate what Mother Earth has to offer. In May, as the heat ramps up, nature winds down, and there are still a couple of fun nature festivals in Florida to enjoy.

36. Hibiscus Festival

Held May 3-5 in Punta Gorda. The 20th Annual Hibiscus Festival presented by the Charlotte County Historical Society to celebrate and share the unique history of Punta Gorda and the town’s ties to world-renowned hibiscus hybridizer, Harry Goulding. The festival is a great way for locals and visitors alike to explore the hibiscus flower and the town’s nickname, “City of Hibiscus”. During this nature festival, explore a variety of activities including live music, plant and craft vendors, and the Lil’ Miss Hibiscus Pageant.

37. Wild Amelia Nature Festival

Held May 10 & 18 in Fernandina Beach. The Wild Amelia Nature Festival is a celebration of the unique bioregion on and around Amelia Island. It features a variety of activities such as nature tours, an Eco-Expo, a nature photography contest and workshops, and a Kids’ Niche. Visitors can also see live animals from Jacksonville Zoo and enjoy live music. In 2024, the festival features Amelia River cruises on May 10 and the EcoExpo on May 18.

Pride Festivals in May

Every year, Pride festivals celebrate and honor the contributions of the LGBTQIA+ community. These events feature parades, rallies, and other activities that draw attention to the issues and struggles faced by the LGBTQIA+ community. They also provide an opportunity to foster acceptance and understanding among people of different orientations and gender identities. Pride festivals provide an opportunity for us all to come together and show our support for the community.

38. Pride: Be Fabulous Arts and Music Festival

Held May 2-4 in Sarasota. The 14th Annual Pride: Be Fabulous Arts and Music Festival is here! This family-friendly event celebrates the spirit of diversity, acceptance, and inclusion, with a lineup of LGBTQ+ music acts, art vendors, food trucks and more. Formerly known as the Harvey Milk Festival, this year’s festival promises to be bigger and better than ever before. Take part in another year of fabulousness by celebrating the diversity of the community.

39. South Florida Pridechilla Music and Arts Festival

Held May 23-27 in Fort Lauderdale. South Florida Pridechilla features five days of events, arts, and music held at venues in Fort Lauderdale and Miami. It’s an event that celebrates the black/BlPOC and LGBTQIA+ community with a variety of activities and fundraisers. From a foam block party to a beach party, Pridechilla promises to be a unique and once-in-a-lifetime experience.

40. Girls in Wonderland

Held May 30-June 2 in Winter Garden. Though GIW calls itself the “premier queer music festival in the country”, it’s not just a music festival so deserves a spot here with the pride festivals. Five days are filled with events that include daily happy hour events, an opening party, a pool parties, a comedy show, dance parties, and after-hours parties. Events will be held at a few different locations around Winter Garden, including the host hotel Springhill Suites, New York Beer Project Orlando, and Mango’s Tropical Cafe.

Florida Watermelon Festivals in May

Florida is the perfect place to celebrate the start of summer with a Watermelon Festival! Every summer, thousands of people gather in various cities to celebrate and enjoy this sweet and juicy fruit. From watermelon carving competitions and seed-spitting contests to live music, there’s something for everyone at these festivals. So grab a slice of deliciousness and enjoy the sweet taste of summer with a celebration at one of Florida’s many watermelon festivals!

47. Rotary Watermelon Festival

Held May 11-12 in Zolfo Springs. This watermelon festival in Zolfo Springs helps to promote area farmers and supports the many projects the local Rotary Club takes on. The day is filled with events, including demonstrations, a car show, and airboat and swamp buggy rides. Centered around the juicy and delicious watermelon, there will also be plenty of watermelon and watermelon-centric dishes from food vendors plus watermelon contests such as seed-spitting.

48. Newberry Watermelon Festival

Held May 18 in Newberry. The Newberry Watermelon Festival has been a part of the town’s culture since 1946. The annual event draws thousands to the small town west of Gainesville and celebrates the town’s favorite fruit – watermelons. The festival includes a beauty pageant, parade with golf cart competition, music performances and a golf cart race. It’s a great opportunity to bring people together and promote unity in the community.

Wine and Beer Festivals

Wine and beer festivals offer the perfect opportunity to celebrate your love of wine and beer. You can sample craft beers from local breweries, try new flavors, or just enjoy the atmosphere with friends. Many festivals also offer food trucks where you can enjoy delicious dishes paired with your favorite drinks.

49. St. Augustine Craft Brewers’ Festival

Held May 4 in St. Augustine. The St. Augustine Craft Brewers’ Festival is a unique event that brings together beer lovers and craft brewers. Attendees are invited to try unlimited samples from 25+ breweries, while enjoying a variety of food vendors, live music, a photo booth and, for the kids, face painting. Not only will festival-goers have tons of fun, but they will also be supporting Brewing a Community – an organization that supports various organizations in need throughout our community, including the St. Augustine Lighthouse and Maritime Museum, Whitney Lab for Marine Bioscience, and St. Johns County Marine Science Program. Don’t miss out on this amazing opportunity to experience St. Augustine’s vibrant craft beer culture!

50. Ormond Beach Beer Festival

Held May 11 in Ormond Beach. In its fourth year, this beer festival in Florida offers a unique opportunity to sample over 100 different beers from over 35 different breweries. Not only can you enjoy beer tasting, but there will be food and other vendors to check out as well. Plus, every purchase made at the event supports the Rotary Club’s charitable mission to help the Ormond Beach community, assist families and children in need, and support local charities. Don’t miss out on this amazing chance to try some of the best beers from around the region, all for a good cause!

51. Beer ‘Merica

Held May 18 in Orlando. Celebrate American Craft Beer Week with a bang at Beer ‘Merica! Sample over 100 different craft brews, seltzers and more. Enjoy delicious offerings from food trucks while enjoying live music. And if that’s not enough, there’s also a $500 cash prize up for grabs for the person wearing the most patriotic gear! Don’t miss this incredible night of fun and raise your glass to the best craft beer America has to offer.

52. Ocean Brews and Blues Beer Fest

Held May 18 in Deerfield Beach. Since 2017, Deerfield Beach transforms itself one day in May into South Florida’s largest beer festival on the beach. Enjoy unlimited samples of 140+ beers from 60+ breweries, while listening to live music and savoring great food. It’s the perfect opportunity to explore new beers, find your favorite brew, and have an unforgettable time with friends.

55. Island Grove Blueberry Festival

Held May 4 in Hawthorne. This annual festival helps support the Cross Creek Volunteer Fire Department which serves the Island Grove, Lochloosa, and Cross Creek communities. Though not well known outside of the immediate area, Cross Creek might sound familiar as the place where Marjorie Kinnan Rawlings wrote her class book set in Florida, The Yearling.

This Florida festival features local artists, artisans, and crafters. Visitors can enjoy homemade blueberry pie or take part in the blueberry cake contest. There’s a kids zone, food trucks, and transportation to and from a nearby u-pick blueberry field.

May Festivals in Florida by Date

Sometimes you don’t know what kind of festival you want to go to, but you do know when you want to go. Here are all the previously listed festivals in Florida by date so that it’s easy to find something to do in Florida on any given weekend in May.

May 1-5

• 1-5: Key West Singers and Songwriters Festival, Key West
• 1-5: Thunder Beach Spring Rally, Panama City Beach
• 2-4: Pride: Be Fabulous Arts and Music Festival, Sarasota
• 3-4: Tampa Riverfest, Tampa
• 3-5: Hibiscus Festival, Punta Gorda
• 3-5: Isle of Eight Flags Shrimp Festival, Fernandina Beach
• 3-5: Sunfest, West Palm Beach
• 4: Bacon, Bourbon, and Blues Festival, Oviedo
• 4: Belleview Founder’s Day Celebration, Belleview
• 4: FORD Cuban Sandwich Festival of Kissimmee and Orlando, Kissimmee
• 4: Howey Founders Day, Howey-in-the-Hills
• 4: Island Grove Blueberry Festival, Hawthorne
• 4: Manatee’s 3rd Annual Taco Fest, Palmetto
• 4: St. Augustine Craft Brewers’ Festival, St. Augustine
• 4-5: ArtsQuest Fine Arts Festival, Miramar Beach
• 4-5: Garden Show and Spring Festival, Williston
• 4-5: 5th Annual Mexican Food Street Fest, Fort Myers
• 4-5: St. Armand’s Circle Aart & Craft Festival, Sarasota
• 4-5: Treasure Coast Seafood Festival
• 5: Casa Tina’s Cinco de Mayo Street Fiesta, Dunedin
• 5: Cinco de Mayo Celebration at Spanish Springs Town Square, The Villages

May 8-12

• 8-12: St. Augustine Food and Wine Festival, St. Augustine
• 9-12: Welcome to Rockville, Daytona Beach
• 10: Wild Amelia Nature Festival – Amelia River Cruises, Fernandina Beach
• 10-11: Drake’s Raid Re-enactment, St. Augustine
• 10-11: St. Pete Taco and Tequila Festival, St. Petersburg
• 11: Cocoa Village Summer Art and Craft Fair, Cocoa
• 11: Family Fest, Altamonte Springs
• 11: Haitian Flag Day Festival, Palmetto
• 11: Ormond Beach Beer Festival, Ormond Beach
• 11: Tomato Festival, St. Augustine
• 11-12: Mayfaire by the Lake, Lakeland
• 11-12: Rotary Watermelon Festival, Zolfo Springs
• 11-12: Vero Beach Seafood Festival, Vero Beach

May 14-19

• 14-27: International Fringe Theater Festival, Orlando
• 16-20: Billy Bowlegs Pirate Festival, Fort Walton Beach
• 17-18: Digital Graffiti Festival, Alys Beach
• 17-19: New Smyrna Beach Jazz Festival, New Smyrna Beach
• 18: Asian Cultural Festival, Ocoee
• 18: As If! North Florida’s 90’s Fest, St. Augustine
• 18: Beer ‘Merica, Orlando
• 18: Homosassa Mullet Toss and Spring Festival, Homosassa
• 18: Newberry Watermelon Festival, Newberry
• 18: Ocean Brews and Blues Beer Fest, Deerfield Beach
• 18: Tacos & Tequila Feast, Fort Lauderdale
• 18: Tupelo Honey Festival, Wewahitchka
• 18: Wild Amelia Nature Festival EcoExpo, Fernandina Beach
• 18-19: Lionfish Derby and Festival, Destin

May 23-31

• 23-26: Jacksonville Jazz Festival, Jacksonville
• 23-27: South Florida Pridechilla Music and Arts Festival, Fort Lauderdale
• 24-26: Blue Crab Festival, Palatka
• 24-26: Florida Folk Festival, White Springs
• 25: Great American Beach Party, Fort Lauderdale
• 25-26: Downtown Delray Beach Memorial Day Weekend Craft Festival, Delray Beach
• 26: Florida Jerk & Music Festival, West Palm Beach
• 26: FORD Cuban Sandwich Festival: Tampa, Tampa
• 26: Tribute to Heroes Block Party & Parade, Lakewood Ranch
• 26-27: Air & Sea Show, Miami
• 26-28: Orlando Carnival Weekend, Orlando
• 27: Davie Memorial Day Parade & Ceremony, Davie
• 27: Green Cove Springs, Green Cove Springs
• 27: Myakka River Blues Festival, Venice
• 27: Pompano Beach Memorial Day Parade & Ceremony, Pompano Beach
• 27: Sarasota Memorial Day Parade, Sarasota
• 27: Wellington Memorial Day Parade & Ceremony, Wellington
• CANCELLED: Sunset Music Festival, Tampa
• 29-6/1: Fiesta Days, Pensacola
• 30-6/2: Girls in Wonderland, Winter Garden
• 30-6/2: Gulf Coast Jam Festival, Panama City Beach

Other Monthly Festival Pages

Looking for other festivals in Florida? Check out all of our Florida festival pages below.