Discover Orlando: May 2026 Event Guide

by Aponte Group

May in Orlando brings a full calendar of experiences that blend culture, community, and high-energy entertainment across Central Florida. From major festivals like Rolling Loud Orlando and the Orlando International Fringe Theatre Festival to seasonal traditions such as SeaWorld’s Seven Seas Food Festival, the month is packed with something happening nearly every day. Local neighborhoods come alive with food truck festivals, outdoor markets, and heritage celebrations, while concert tours, comedy shows, and cultural events keep the entertainment scene thriving. As spring transitions into summer, May is the perfect time to explore everything Orlando has to offer, whether you are enjoying family-friendly events, discovering local flavor, or catching a live performance across the city.

As spring transitions into summer, May is the perfect time to explore everything Orlando has to offer, from family-friendly events and local food spots to live performances and the latest in entertainment.

Ongoing Throughout May
National Heritage Month | National Investors Month | National Moving Month | Small Business Month

SeaWorld Orlando Seven Seas Food Festival & Concerts
Through the 17th

May 1st
National Principal’s Day

Ocoee Cindo de Mayo Block Party

Matt Mathews: Boujee On A Budget Tour

May 2nd
National Brothers and Sisters Day

Boxi Park Derby Day

Perreo at 9AM: Orlando

'Somebody Feed Phil' Food Tour

Clermont 8th Annual Spring Garden Festival

Jess Hilarious at The Plaza Theatre

24th Annual MAKE 'm SMILE

Free Comic Book Day 2026 at Coliseum of Comics Millenia

May 3rd
Hurricane Preparedness Week
Through the 9th

Cars & Coffee Central Florida at The Fountains

Kissimmee Puerto Rican Heritage Night

Lake Underhill Orlando Seafood Pop Up

May 4th
Star Wars Day

May 5th
Cinco de Mayo | Nail Day | National Hoagie Day

Cinco de Mayo Street Party & Celebration at Promenade at Sunset Walk

Orange County's Asian American & Pacific Islander Heritage Celebration

May 7th
National Tourism Day

Curren$y at The Abbey

May 8th
National Military Spouses Day

Ari Lennox: The Vacancy Tour

Rolling Loud Orlando
Through the 10th

Blessd: El Mejor Hombre Del Mundo Tour

May 9th
Mother’s Day Food Truck Festival at Dezerland Park
Through the 10th

Orlando Carnival Downtown: Miss Orlando Carnival Queen Pageant

Whiskey Riot: A Festival of Whiskeys

City of Kissimmee Mother & Son Dance

May 10th
Mother’s Day | National Golf Day | National Small Business Day