PENSACOLA NAVY DAYS Celebrate Pensacola’s rich military heritage with a weekend of events honoring our service members. More details:pensacolanavydays.com
- Date: Friday, May 9 – Sunday, May 11
- Time: Varies
- Location: Various
Night at the Museum Gala – Friday, May 9, 6:30 PM at the National Naval Aviation Museum. Enjoy cocktails, dinner, and dancing in a black-tie setting.
Navy Days 4K Run/Walk – Saturday, May 10, 8:00 AM starting at Plaza DeLuna. Participate in a 2.4-mile race through downtown Pensacola.
Navy Days Parade – Saturday, May 10, 9:30 AM along Pensacola’s waterfront. Experience a parade featuring military equipment, bands, and drill teams.
Fun Fest at Plaza DeLuna – Saturday, May 10, 12:00–3:00 PM. Enjoy family-friendly activities, food trucks, and military displays. pensacolanavydays.com
BANDS ON THE BLACKWATER Head to Milton’s Riverwalk for this free outdoor concert series. Bring your lawn chairs and enjoy live music by local bands along the Blackwater River. More details: https://www.facebook.com/BandsOnTheBlackwater/
- Date: Friday, May 9
- Time: 7 – 9 p.m.
- Location: Milton’s Riverwalk
PENSACOLA BEACH ART & WINE FESTIVAL Sip, stroll, and shop your way around the Pensacola Beach Boardwalk as it transforms into an artist and wine lover’s paradise. Enjoy local art, live music, and wine tastings with a stunning Gulf backdrop. More information here: visitpensacola.com
- Date: Saturday, May 10
- Time: 11 a.m. – 4 p.m.
- Location: Pensacola Beach Boardwalk
“THE TRAIL TO OREGON” Embark on a comedic journey with this musical parody of the classic Oregon Trail game. Laughter guaranteed! 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. Trail Tickets Here
- Date: Thursday, May 8 – Sunday, May 11
- Time: Varies; Several Shows sold out, so act fast
- Location: Pensacola Little Theatre
UWF HISTORIC TRUST OPEN HOUSE All visitors to the site will enjoy FREE ADMISSION to all of the UWF Historic Trust museums and downtown sites including the Pensacola Museum of Art, Pensacola Museum of History, Pensacola Children’s Museum and Historic Pensacola Village. Living history actors will share information and memorabilia from different periods of history for visitors of all ages. https://historicpensacola.org/
- Date: Saturday, May 10
- Time: 10 a.m. – 2 p.m.
- Location: All UWF Trust Museums & downtown sites.
PALAFOX MARKET Rain or shine, this vibrant market offers fresh produce, baked goods, local art, and more—perfect for a Saturday morning stroll.
- Date: Saturday, May 10
- Time: 9 a.m. – 2 p.m.
- Location: MLK Plaza and Plaza Ferdinand; shuttles avail.
MOTHER’S DAY Mother’s Day does not have to be complicated. If the mother in your life has children in elementary school or younger, she wants a break. (Okay, maybe middle school, too) If her children are high school and older, what she wants is TIME WITH YOU. Time, a momento of thanks, heartfelt words of appreciation, a million dollars, maybe a flower. Literally everything else is icing. Call a brunch spot, take pictures together, rent her a beach chair, bring her a plant or flowers. And if you still have your Mama, hug her and thank God.
- Date: Sunday, May 11
- Time: ALL DAY LONG (All week long; ALL YEAR LONG)
- Location: Anywhere but the laundry room or kitchen
THE EASTHILLBILLIES AT CALVERT’S Tiger Beat Large Print Edition calls them a “four-person jukebox of adorable proportions.” We agree, Tiger Beat…we agree. Is Tiger Beat still around? We Googled…it ended in 2021 as an online edition. Anywho! Go support local and live!
- Date: Sunday, May 11
- Time: 4 p.m. – 7 p.m.
- Location: Calvert’s in the Heights
GULF BREEZE ZOO ADVENTURE Visit the Gulf Breeze Zoo and explore its 50-acre park featuring over 900 exotic animals. Enjoy activities like hand-feeding giraffes and riding the African preserve train. https://www.gbzoo.com/
- Date: Every day of the year except Thanksgiving & Christmas
- Time: 9 a.m. – 5 p.m. from Mar. 1 – Nov. 2
- Location: 5701 Gulf Breeze Pkwy, Gulf Breeze, FL 32563
JOYWAVE: HERE TO PERFORM…SPRING 2025 Indie rock fans, rejoice! Catch Joywave live for an unforgettable night of music and energy. Tickets here: JOYWAVE
- Date: Sunday, May 11
- Time: 7 p.m. doors open; 7:30 p.m. – show
- Location: Vinyl Music Hall
It’s TRIVIA NIGHT at Dog House Downtown!
Think you’ve got what it takes to be the trivia champ? Grab your smartest friends and head our way—trivia kicks off at 6 PM sharp!
Thursday specials:
$10 Fish Sandwich + Beer Combo
$6 Craft Cocktails
$5 Well Shots
Whether you’re in it to win or just here for the laughs and good eats, we’re celebrating a Thursday night tradition full of fun, food, and friendly competition.
Let’s make it a night to remember!
See you at Dog House—where the answers are questionable, but the vibes are always right!
