Italian nights take over downtown, wine returns to the beach, and one of the biggest pickle and wings festivals the Gulf Coast has ever seen lands at Seville Square.
Whether you’re catching live music in Milton, dancing to 2000s throwbacks at Vinyl, or supporting animal welfare at the Shaka Bar, this is a weekend packed with reasons to get out and explore what Pensacola has to offer.
Here’s the top 10 for the weekend.
Downtown Pensacola’s monthly street festival celebrates Italian heritage with 70+ art vendors, live music, performances, and food throughout the streets.
- Date: Friday, May 15
- Time: 5:00pm–9:00pm
- Location: Downtown Pensacola (Government St, Plaza Ferdinand, Zaragoza St)
PENSACOLA BEACH ART & WINE FESTIVAL
Finally rescheduled after last weekend’s weather, this beachside wine and art festival spans two premier locations with 50+ wine selections, 20+ local artists, live music on two stages, and Grand Tasting access.
- Date: Sunday, May 17
- Time: 12:00pm–5:00pm (Grand Tasting: 2:00pm–5:00pm)
- Location: Pensacola Beach Boardwalk & Gulfside Pavilion
HOME SWEET HOME GULF COAST BLOCK PARTY
A free, family-friendly expo and community block party connecting homeowners with local businesses, interactive activities, food, music, and games at Blue Wahoos Stadium.
- Date: Saturday, May 16
- Time: 12:00pm–4:00pm
- Location: Blue Wahoos Stadium, 351 W Cedar St
A beach event celebrating endangered marine animals with environmental education, live music from Katie Dineen, and advocacy for Gulf wildlife protection.
- Date: Saturday, May 16
- Time: 9:00am–11:00am
- Location: Gulfside Pavilion, Pensacola Beach
PENSACOLA PICKLES & WINGS FAMILY FESTIVAL
An all-day festival featuring pickle-inspired creations, wings in every style, food trucks, live music, costume contests, the Pickle Priest, and kids’ activities beneath Seville Square’s oak trees.
- Date: Saturday, May 16
- Time: 10:00am–8:00pm
- Location: Seville Square, 311 E Government St
A community fundraiser benefiting Escambia County Department of Animal Welfare featuring delicious BBQ plates and adoptable dogs. Hosted by Rushing Partners and WolfGang LLC at the beach’s favorite tiki bar.
- Date: Saturday, May 16
- Time: 3-hour event
- Location: The Shaka Bar, 649 Pensacola Beach Blvd
Free outdoor concert series along the Blackwater River featuring live music from 7:00pm–9:00pm every Friday night. This week: Blackwater Calvary performs.
- Date: Friday, May 15
- Time: 7:00pm–9:00pm
- Location: Jernigan’s Landing, 5158 S Willing St, Milton
THE MAX BEACH VOLLEYBALL TOURNAMENT
The 5th annual charity beach volleyball tournament benefiting Rally Foundation for Childhood Cancer Research Gulf Coast, held at Salty Rose.
- Date: Saturday, May 16
- Time: 10:00am (Check-in: 9:00am)
- Location: Salty Rose at The Pensacola Beach Resort
ASIAN/PACIFIC AMERICAN FESTIVAL
A two-day cultural celebration featuring authentic Asian and Pacific Islander cuisine, live performances, traditional dances, cultural exhibits, and family activities.
- Date: Saturday–Sunday, May 16–17
- Time: Both days
- Location: Fil-Am Cultural Center, 234 W Oakfield Rd
The Gulf Coast’s biggest outdoor vintage clothing festival returns with 40+ vendors specializing in vintage clothes, housewares, records, art, and sustainable fashion from the 1970s to 1990s. Free to attend with live music.
- Date: Sunday, May 17
- Time: 1:00pm–6:00pm
- Location: The Handlebar, 319 N Tarragona St
Local Pulse Top 10 Brought to You by The Dog House
We’ve got a secret, downtown Pensacola.
Something exciting is coming to the Jefferson alleyway…
Here are some hints to tide you over until the big reveal:
It’ll be bold.
It’ll be bright.
It’ll be blocking out those blazing UV rays, making patio lunches with us a lot less sweaty!
Any guesses?
