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May 2019: Our Favorite Events Throughout Florida

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.

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. www.sunfest.com


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, & activities for kids! You’ll find it all downtown May 3-5, 2019 at the historic Colonial Quarter in beautiful St. Augustine, Florida. www.gamblerogersfest.org

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 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 celebration every May, 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 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 family fun! www.shrimpfestival.com/

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 gathering. The fair concentrates on restoring land affected by hurricane destruction. https://www.pleinairfl.com

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 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 free. www.keywestsongwritersfestival.com

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 up-close visits with the Center’s Educational Ambassador birds. Visitors will be able to view non-releasable orphaned raptors (birds of prey) being raised at the Center, if available. fl.audubon.org/chapters-centers/baby-owl-shower

7th Annual Key Lime Festival, Punta Gorda
May 11, 2019


Enjoy family-friendly games and activities all day, along with music and dancing. 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, milk shakes, 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. https://www.fishville.com/event/key-lime-festival-2/

9th Annual Sea Turtle Festival, Titusville
May 11, 2019

This is a FREE family fun community event. Highlights include Sea Turtle artists, crafters, turtle talks, live entertainment, music, dance groups, and 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! Plus you will learn simple things you can do to protect endangered sea turtles with the Canaveral National Seashore and Sea Turtle Preservation Society. www.downtowntitusvillefl.com/sea-turtle-festival–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, Galactic & many more. The event will take place at the Iron Cow. Doors open at 9pm. 21 & up. $10 cover. Lots of free parking near the venue! www.facebook.com/phatnjazzy/ 

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, Mayfaire is located on the shores of beautiful Lake Morton in downtown Lakeland, Florida. Mayfaire is 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 9am to 4pm. www.mayfairebythelake.org/

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 even 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. 9am to 4pm. Free. www.windsor-z-news.org/events.html

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 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 required for indoor plays. Outdoor performances, art exhibits and weekend kids’ activities are free. orlandofringe.org

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 Grumpy Ole Trolls. Friday-Sunday 3 Day Passes are $90; Thursday-Sunday 4 Day Passes are $110. All tickets include primitive camping. orangeblossomjamboree.com

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 5pm. Bring new or nearly new used books for kids up to 12th grade! Don’t have books? Cash contributions will 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. orlandorotary.org/event/2019-great-rotary-swan-boat-race

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, along with loads small-town charm. 9am – 4pm. www.tupelohoneyfestival.com/

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 Patatka. Free admission. (Note: the Gatorland Ski Show is at 12:15pm, not a.m.)  www.facebook.com/bluecrabfestivalpalatka/

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 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,jacksonvillejazzfest.com

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 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.

Here’s an article we wrote on the 2018 Florida Folk Festival: http://www.authenticflorida.com/articles/where-to-go/celebrate-the-66th-annual-florida-folk-festival-memorial-day-weekend/

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