Top Florida Events in May 2026

by Melanie Lentz-Janney

We’ve narrowed our list of Florida events in May to a few of our personal favorites that you won’t want to miss.

Leu Gardens walkway in Orlando, Mother's Day

These events are sprinkled throughout the Sunshine State, so we recommend planning a weekend getaway and exploring the surrounding areas.

30th Annual Key West Songwriters Festival – Key West

When: April 29^th through May 3^rd, 2026

Where: Various Key West venues, Key West – Schedule and venue list coming soon.

More information: The Key West Songwriters Festival is five days of live music, with shows running from morning to late at night.

This festival takes you all over the island to different locations and has over 100 artists in the lineup.

Learn more about the event on the Key West Songwriters Festival Website.

Tips for the Event

Get there early to get a good seat. While there are many free concerts, there can be long lines.

While you’re in the area, make sure to check out our tips for A Trip to Authentic Key West.

61st Isle of Eight Flags Shrimp Festival – Fernandina Beach

When: May 1^st through May 3^rd, 2026

Where: 102 Centre Street, Fernandina Beach, Florida 32034

More Information: Located in downtown Fernandina Beach, the Eight Flags Shrimp Festival has many activities for the whole family.

Don’t miss the Parade the day before the festival kicks off.

The Shrimp Fest features tons of fresh seafood and shrimp, and over 300 artists and craftspeople. You can purchase jewelry, photography, pottery, and more.

Let the kids play in the Kid Zone, and you will also be able to enjoy live music on two stages, contests, and pirates to entertain you.

There is also a decorated shrimp boat contest, followed by a blessing of the fleet and a laying of the wreath.

Learn more about the event from the Shrimp Festival website.

Tips for the Event

The parade starts at 6:00, rain or shine. Get a spot for the parade early.
There is a vintage and antique sale at the event that you are sure to enjoy. Make some time to stop in and see the vintage and antique items.

While in the area, check out the Top Things To Do on Amelia Island and visit the Pippi Longstocking House in Fernandina Beach.

19^th Annual Pinellas Pepper Fest – Pinellas Park

When: May 2^nd and 3^rd, 2026

Where: England Brothers Bandshell Park, 5010 81^st Ave. N, Pinellas Parks, FL 33781

Description: Pinellas Park’s spiciest event of the year has plenty of things to enjoy, including spicy contests, sauces, salsas, barbeque, beer, and live music.

This event is free to attend.

Learn more by visiting the official Pinellas Pepper Fest Facebook page.

Tips for the Event

Admission is free, but bring cash to purchase your own pepper plants and seasonings to take home.
Check the event schedule so you don’t miss any of the incredible entertainment available.

While you are in the area, don’t miss: Authentic Things to Do in Tampa, Florida

7th Annual First Responders Appreciation Day (Hero Fest) – Merritt Island

When: May 3^rd, 2026

Where: 400 S. Sykes Creek Parkway, Merritt Island, FL 32952

More Information: It’s time to celebrate Brevard County First Responders. Are you a member of Law Enforcement, a Firefighter, EMS, or a Dispatcher? Don’t miss this event that is here for you.

If you are not a first responder, don’t feel like you have to skip this event. In fact, you are welcome to come help celebrate the first responders who protect and serve you each day.

Learn more on the Back Brevard Heroes website.

Check out our Reasons to Visit Florida’s Space Coast

St. Augustine History Festival – St. Augustine

When: May 6^th through May 10^th, 2026

Where: Various locations in St. Augustine

More Information: St. Augustine invites you to enjoy special events at 30 historical sites throughout the city.

You can tour some historical locations, hear from fabulous speakers, and join a historic walking tour.

Check the St. Augustine History Festival Facebook Page to see more about the different events and offerings as part of the festival.

Castillo de San Marcos in St. Augustine aerial

Participating Venues

Castillo de San Marcos National Monument
St. Augustine Alligator Farm Zoological Park
National Shrine of Our Lady of La Leche at Mission Nombre de Dios – Catholic Diocese of St. Augustine
City of St. Augustine Archaeology Program and Historic Preservation
Colonial Quarter
Flagler College, former Ponce de Leon Hotel
Florida National Guard Museum and St. Augustine National Cemetery
Fort Mose State Park and Museum – Fort Mose Historical Society

Photo of a conquistador helmet at the Fountain of Youth

Fountain of Youth Archaeological Park
Governor’s House Cultural Center and Museum
Lincolnville Museum and Cultural Center
Lightner Museum
The Woman’s Exchange of St. Augustine – Peña-Peck House
Spanish Military Hospital Museum, St. Augustine, Florida
Saint Augustine Historical Society – Oldest House Museum Complex
St. Augustine Lighthouse and Maritime Museum
Ximenez-Fatio House Museum
Villa Zorayda Museum

CHURCHES

Cathedral Basilica of St. Augustine
First Congregation Sons of Israel
St. Benedict the Moor Catholic Church
St. Cyprian’s Episcopal Church
Ancient City Baptist Church
Memorial Presbyterian Church
National Shrine of Our Lady La Leche
Trinity Parish
St. Paul A.M.E. Church
St. Photios Greek Orthodox National Shrine

HISTORIC GARDENS

Father Miguel O’Reilly House and Gardens
Fountain of Youth Archaeological Park
Nombre de Dios Historic Grounds and Gardens
Peña-Peck House Historic Gardens
Spanish Military Hospital Apothecary Garden
UF: Resilient Florida Natives and Landscape Design
Ximenez-Fatio House Gardens

HISTORIC CEMETERIES

First Congregation Sons of Israel Cemetery
Pinehurst and San Sebastian Cemeteries
St. Augustine National Cemetery
Tolomato Cemetery

While in the area, don’t miss the Top Things to Do in St. Augustine.

Mayfaire By-The-Lake Fine Art Festival – Lakeland

When: May 9^th and 10^th, 2026`

Where: Lake Morton Dr, Lakeland, FL 33801

More Information: Mayfaire by the Lake started as a small art fair in 1971 and has quickly grown to one of the largest outdoor art events in the state. Visit over 150 booths of unique artists.

Mayfaire By the Lake Group of people enjoying the event — Source: Polk Museum of Art

Enjoy this charming walk through downtown Lakeland as you look for your next favorite art piece.

Learn more from Mayfaire by the Lake.

While in the area, enjoy some of the Best Things to do in Lakeland.

Wild Amelia Nature Festival (Eco Expo) – Fernandina Beach

When: May 8^th through the 16^th, 2026

Where: 2500 Atlantic Ave, Fernandina Beach, FL 32034

More Information: It’s time to learn more about making Fernandina Beach beautiful. A variety of seminars are offered, and different local organizations share more about the area and how to care for it.

Explore classes about the animals and nature that Fernandina Beach has to offer.

Learn more on the Fernandina Beach Calendar.

Fort Lauderdale Air Show 2026 – Fort Lauderdale

When: May 9^th through the 10^th, 2026

Where: 18th Street to Sunrise Blvd. on the beach in Fort Lauderdale

More Information: It’s time to celebrate aviation at the Fort Lauderdale Air Show. You have the chance to see a variety of military planes take to the sky.

Sit on the beach and watch a three-hour air show like no other.

See the Blue Angels, Polaris Program Ghost Squadron, A-10C Thunderbolt II Demonstration Team, and many more as part of the show.

Learn more on the Fort Lauderdale Air Show website.

While in the area, don’t miss the Things to Do in Ft. Lauderdale Most Spring Breakers Miss.

16th Annual Fort Myers Film Festival

When: May 20^th through the 24^th, 2026

Where: Fort Myers Film Festival, 2301 1st St, Fort Myers, FL 33901

More Information: Get ready to celebrate film and view a variety of films as part of the Fort Myers Film Festival. You do not want to miss this.

Since you are visiting Fort Myers, don’t miss out on the Ultimate Guide to Fort Myers and Fort Myers Beach

Are you a fan of Florida Film Festivals? Check out A Guide to Film Festivals in Florida

74th Annual Florida Folk Festival – White Springs

When: May 22^nd through the 24^th, 2026

Where: 11016 Lillian Saunders Dr, White Springs, FL

More Information: The Florida Folk Festival is a three-day celebration of the music, dance, stories, crafts, and food that make Florida unique.

From Irish fiddle tunes, contra dancing, and root beer floats to the vast varieties of music of immigrants, the state’s cultural heritage reflects the lives of generations of Florida families and communities.

Florida Folk Festival 2023 — Source: Florida State Parks

Learn more about the event from Florida State Parks.

Before you head out to the Florida Folk Festival, get to know the area: Things To Do in White Springs, Florida

Palatka Blue Crab Festival – Palatka

When: May 22^nd through the 24^th, 2026

Where: Riverfront Park – 100 Memorial Pkwy, Palatka, FL 32177

More information: The Palatka Blue Crab Festival is a 3-day, family-friendly festival held in downtown Palatka.

The cherished event features top national performers, an all-day lineup of regional musicians, vendors, food trucks, carnival rides, and tons of blue crabs.