Top 10 Events in Pensacola for the weekend of Thursday, May 1 – Sunday, May 4, 2025. Whether you’re into festivals, live music, family fun, or unique local experiences, there’s something for everyone to enjoy.
CORKS FOR A CAUSE Join Northwest Florida Guardian ad Litem for an event brings together our community to support advocacy for abused, abandoned, and neglected children in Northwest Florida. Live music by Roman Street Band, heavy hors d’oeuvres by Classic City Catering, a variety of red and white wine.
- Date: Thursday, May 1
- Time: 5:00 p.m. – 8:00 p.m.
- Location: 5eleven Palafox
For tickets, click here: Corks for a Cause Tickets
COMMUNITY MOVIE NIGHT FEATURING MOANA 2 Bring the family to Blue Wahoos Stadium on Friday, May 2 for Moana 2 Movie Night, featuring food, inflatables and fun! The movie begins at 6:00. No chairs or outside food and drinks are allowed – concession options will be available for purchase.
- Date: Friday, May 2
- Time: Gates open at 5:00 p.m.; Movie Starts at 6:00 p.m.
- Location: 5eleven Palafox
TRAIL TO OREGON Trail to Oregon is a lively and humorous musical that follows the misadventures of a quirky pioneer family as they journey westward along the Oregon Trail in the 19th century. Led by the bumbling but well-meaning Father, the family encounters a series of obstacles and colorful characters along the way, including bandits, buffalo stampedes, and the dreaded dysentery.
- Date: Friday, May 2 at 7:30 p.m. – May 11 at 2:30 p.m.
- Time: Times vary; check website for more
- Location: Pensacola Little Theatre
https://www.pensacolalittletheatre.com/shows-and-events/trail-to-oregon
BURGER BATTLE BY THE BAY is a fundraiser that benefits Take Stock in Children of Florida and Pensacola Suburban West Rotary Club Foundation. Sample burgers from all cook teams and vote for your favorite (essentially it’s all you can eat burgers!)
- Date: Saturday, May 3
- Time: 11 a.m. – 1:30 p.m.
- Location: Community Maritime Park, Downtown Pensacola
https://www.facebook.com/burgerbattlebythebayPensacola/
KENTUCKY DERBY PARTIES Calvert’s, 200 South, and Old Hickory Bar are all having Kentucky Derby events.
Calvert’s event begins at 10 a.m.; Old Hickory starts at 2 p.m.; 200 South at noon. Don your dapper duds a la Derby and gets ready for the fastest event in sports. Mint juleps, bow ties, and sheer excitement are central to every first Saturday in May.
Details on Calvert’s here.
Details on Old Hickory here.
Details on 200 South here.
KENTUCKY DERBY PARTY BENEFITTING THE SAKEY FOUNDATION *Must purchase ticket to attend! One ticket includes appetizer buffet and 3 drink tickets* benefitting The Sakey Foundation, a Non-Profit organization serving the greater Pensacola area.
Their mission is to provide sports equipment & opportunities to youth with limited income in both Escambia & Santa Rosa counties.
- Date: Saturday, May 3
- Time: 4:00 p.m. – 9:00 p.m.
- Location: The Burrow
- Date: Saturday, May 3
- Time: 6:30 p.m. – 9:00 p.m.
- Location: Studer Community Institute
BEARLY DEAD Dead & more like never before! Bearly Dead, a nationally-touring Grateful Dead tribute, is a true party band delivering a full-spectrum live experience filled with danceable energy, extraordinary performance antics, and world-class musicianship. The band’s concert-style show celebrates the journey of the Grateful Dead from their earliest records until their final tours while weaving in potent classics from notable jam, rock, and funk artists.
- Date: Saturday, May 3
- Time: 7:00 p.m.
- Location: The Handlebar
Tickets: Bearly Dead
PENSACOLA SYMPHONY ORCHESTRA: SEASON FINALE The season concludes with a thrilling finale, featuring Dvořák’s Sixth Symphony and Le Corsaireby Berlioz. Soloist Maxim Lando joins the orchestra for Saint-Saëns’ Second Piano Concerto.
- Date: Saturday, May 3
- Time: 7:30 p.m.
- Location: Saenger Theatre
TACO EATING CONTEST Do you like Tacos? If so, come and sign up at our annual Taco Eating Contest in celebration of Cinco de Mayo!! The winner receives $50 cash, Tacos Rock Gift Card and a Cinco de Mayo T-shirt!!
- Date: Monday, May 5
- Time: 4:00 p.m.
- Location: Tacos Rock in Gulf Breeze
What’s crispy, refreshing, and golden brown all over?
Our Thursday $10 Mullet and Brew Special!🙌
Stop in and treat-yo-self to the deal of the day, and don’t forget to grab the crew and join us for Trivia Night!
👉7 pm
👉Hosted by Jarrell Hendrix
👉winner takes home a DH Giftcard
The grills are lit and we’re ready for ya.
See you soon Pensacola!
