May 2019: Our Favorite Events Throughout Florida

The month of May is jam-packed with some fantastic festivals/events. We’ve narrowed our May list down to a few of our personal favorites. We highly recommend planning a weekend getaway and exploring the surrounding areas of these festivals. Their locations are chock full of authentic treasures. Read on to check out our favorite May Events in Florida!


37th Annual SunFest, West Palm Beach

May 2-5, 2019



SunFest is Florida’s largest waterfront music and art festival held annually in downtown West Palm Beach. The national headliners include Keith Urban, OneRepublic, Earth, Wind & Fire, The B-52s, and more. Fun facts: More than 2,000 volunteers support SunFest; last year people traveled from 49 states, 31 countries, and more than 200 cities outside of Palm Beach County; Economic impact to the area is more than $15 million.


The 24th Annual Gamble Rogers Music Festival, St. Augustine

May 3-5, 2019



A three-day music festival is held in St. Augustine the first weekend each May, featuring dozens of national, regional, and local musicians and storytellers on several stages. 50+ bands on 3 stages, new Folk School workshops, & also activities for kids! You’ll find it all downtown May 3-5, 2019 at the historic Colonial Quarter in beautiful St. Augustine, Florida.


The 56th Annual Isle of Eight Flags Shrimp Festival, Fernandina Beach

May 3-5, 2019



The 56th Annual Isle of Eight Flags Shrimp Festival will be held on May 3-5, 2019. Fernandina Beach is the birthplace of the modern shrimping industry, and its historic downtown pulls out all the stops at this beloved May Event in Florida, which has been a part of Island life for over 50 years. One of the premier festivals in the Southeast, the Festival brings together the love of shrimp and also the best of arts and entertainment, all set in the beautiful Historic District of Fernandina Beach, Florida. Enjoy the fine arts and crafts, antiques, regional and local music, shrimp caught and served locally, seafood dishes, The Pirate’s parade, fireworks, and also family fun!


Forgotten Coast En Plein Air, Apalachicola

May 3-12, 2019



World-renowned artists convene to portray the scenery and culture of old Florida through painting at this ten-day May event in Florida. The fair also concentrates on restoring land affected by hurricane destruction.


24th Annual Key West Songwriters Festival, Key West

May 8–12, 2019



Music fans descend on the streets of Key West to hear songwriters perform on stages from beaches to boats to bars and also historic theaters. The 24th annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Over 200 performers and over 50 shows, and most shows are also free.


Baby Owl Shower, Maitland

May 11, 2019



Each year the Audubon Center for Birds of Prey in Maitland (North of Orlando) hosts the Baby Owl Shower to help support clinical programs during their busiest season. They ask for in-kind donations in lieu of admission. The wishlist is available on their website. Fun for the whole family, the Center hosts special conservation-themed activities, games, and also up-close visits with the Center’s Educational Ambassador birds. Additionally, visitors will be able to view non-releasable orphaned raptors (birds of prey) being raised at the Center, if available.


7th Annual Key Lime Festival, Punta Gorda

May 11, 2019




Enjoy family-friendly games and activities all day, along with music and dancing at this May event in Florida. Village merchants will feature specialties like key lime-scented Florida sea salts and soap, as well as all manner of key lime goodies, including gelato, ice cream, milkshakes, yogurt, pie, fudge, marinade, dips, jelly, candy, almonds, truffles, cookies, limeade, taffy, olive oil, balsamic vinegar, and “Lime-a-Ritas.” Free admission. 10 a.m. to 4 p.m.


9th Annual Sea Turtle Festival, Titusville


May 11, 2019



This May event in Florida is a FREE family fun community event. Highlights include Sea Turtle artists, crafters, turtle talks, live entertainment, music, dance groups, and also an opportunity to get your photo w/ a live mermaid! There’s also face painting, chalk art, a bounce house, sea turtle crafts for kids, and more! Additionally, you will also learn simple things you can do to protect endangered sea turtles with the Canaveral National Seashore and Sea Turtle Preservation Society.–thirsty-turtle-beer-crawl.html


Phat-N-Jazzy 25th Anniversary Celebration, Orlando

May 11, 2019



Celebrate 25 years since the launch of Phat-N-Jazzy, a weekly party dedicated to the music loved by so many! Listen to acid jazz, funk, soul, jazzy hip hop, downtempo, trip-hop & global sounds dominated their playlists & the roster of international artists who blessed their stage. Some of their past guest artists included DJ Krush, Blackalicious, Ghostface Killah, Sharon Jones & The Dap-Kings, Mr. Scruff, Mark Farina, and also Galactic. The event will take place at the Iron Cow. Doors open at 9 pm. 21 & up. $10 cover. Lots of free parking near the venue! 


Mayfaire by-the-Lake, Lakeland

May 11 & 12, 2019


Began as a crafts fair on the lawn of the Lakeland Public Library, Mayfaire by-the-Lake has grown into one of Florida’s premier outdoor art festivals. Held on Mother’s Day weekend each year, this May event in Florida is located on the shores of beautiful Lake Morton in downtown Lakeland, Florida. Mayfaire is also one of the largest and oldest outdoor art festivals in Central Florida, ranked number 45 among Sunshine Artist Magazine’s “200 Best Art Shows” in 2018. Come see why it has such a great reputation! From 9 am to 4 pm.


Windsor Zucchini Festival, Windsor

May 12, 2019



For 35 years, the folks in this Alachua County city celebrate the zucchini with a zucchini contest, zucchini carving a Duke of Zuke & Zuqueenie Pageant, and also zucchini ice cream. The event also features live music, kid’s activities, a raffle, arts and crafts, and plant sale. Held at the Windsor Fire Station grounds east of Gainesville. 1401 Co Rd 234. 9 am to 4 pm. Free.


28th Annual Orlando Fringe Festival, Orlando

May 14-27, 2019



The Orlando Fringe is the longest-running Fringe Theatre Festival in the United States, celebrating 28 years as “Orlando’s Most Unique Cultural Experience.” Fourteen days of 200+ short plays, musical performances, magic acts, and also a visual-art exhibition. Headquartered at Loch Haven Park (off Princeton Street between Orange and Mills avenues, north of downtown Orlando), 100% of ticket sales are given back to the artists. General Admission is $35; $10 button plus tickets also required for indoor plays. Outdoor performances, art exhibits, and also weekend kids’ activities are free.


Orange Blossom Jamboree, Brooksville

May 15-19, 2019



Visit the Sertoma Ranch for four days of jam bands and themed nights. Over 50 bands will be performing including The Heavy Pets, Mind Medicine, Soul Jam and also Grumpy Ole Trolls. Friday-Sunday 3 Day Passes are $90; Thursday-Sunday 4 Day Passes are $110. All tickets also include primitive camping.


Great Rotary Swan Boat Race, Orlando

May 16, 2019



Come join the fun as organizations compete for the Golden Swan award for the fastest swan boat! The Great Rotary Swan Boat Race at Lake Eola Band Shell will take place on Thursday, May 16, at 5 pm. Bring new or nearly new used books for kids up to 12th grade! Don’t have books? Cash contributions will also be gratefully accepted by ‘A Gift For Teaching‘. All monies will be used to purchase books. All books will be distributed to students in need of additional reading materials.


Annual Tupelo Honey Festival, Wewahitchka, FL

May 18th, 2019



Under the great mossy oaks of Lake Alice, people come from all over the world to Wewahitchka, Florida to taste and take home the country’s finest Tupelo Honey. Food, fun, music, art … it’s all there, also with loads of small-town charm. 9 am – 4 pm.


Palatka Blue Crab Festival, Palatka

May 24-27, 2019




Canceled in 2018, the festival returns in 2019 as Florida’s largest Memorial Day celebration. Festivities include a Memorial Day Parade, seafood cook-off, live entertainment, helicopter and airboat rides, arts and crafts, antiques, and more. Everything happens at the Palatka Riverfront in Downtown Palatka. Free admission. (Note: the Gatorland Ski Show is at 12:15 pm, not a.m.)


2019 Jacksonville Jazz Festival, Jacksonville


May 23-26, 2019



Join the City of Jacksonville May 23 – 26 and experience two stages of live jazz, local food, drinks, shopping, and also entertainment.  Since first taking place in 1981, the Jazz Fest has become one of the largest jazz festivals in the country, offering a fun and vibrant street festival atmosphere, and in 2019 you can experience it throughout 10 blocks of downtown – all for free! www,


67th Annual Florida Folk Festival, White Springs

May 24-26, 2019



On Memorial Day Weekend the Stephen Foster Folk Cultural Center State Park in the little hamlet of White Springs abounds with the sounds and sights of Florida’s finest music, dance and also stories. The Florida Folk Festival presents the roots of Florida’s many cultures as performers gather from little towns and large cities. One of the oldest state folk festivals in America, the event now brings 30,000+ concert-goers to the festival site each year to hear more than 300 performances on multiple stages. Admission starts at $25 for adults.

Want to learn more about the Florida Folk Festival? Check it out here! was named Best Travel Blog two-times at the Florida Sunshine Awards.
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