THU 10/1–SUN 10/11
Pensacola Beach Songwriters Festival (cherry-pick sets)
22+ venues, Pensacola Beach + downtown
Ten days of acoustic storyteller rounds run, mostly free, a build-your-own date.
Venue-by-venue schedule
Last quarter · 37% lit3101825
Pensacola Beach & Perdido
Everything checked within reach of Pensacola Beach & Perdido.
Pensacola Beach & Perdido
35 events and 18 places
Mondays
Perdido Run Club (Fleet Feet, Mondays)
Hub Stacey's at The Point · Pensacola
Perdido Run Club is a weekly Fleet Feet run or walk club that meets at Hub Stacey's at The Point, 5851 Galvez Rd, in the Perdido Key area.
6 PM
Tuesdays thru TUE 10/27
Bands on the Beach: free Gulfside concert
Gulfside Pavilion, Pensacola Beach
Live music beside the Gulf every Tuesday evening, free, with the sand right there.
7:00-9:00 PM
Tuesdays thru TUE 10/27
Bands on the Beach
Gulfside Pavilion at Casino Beach · Pensacola Beach
A free beach concert plays every Tuesday at the Gulfside Pavilion, 7:00 PM to 9:00 PM.
7:00-9:00 PM
21+Tue thru FRI 10/16
Live Music: Paradise Bar & Grill
Paradise Bar & Grill · Pensacola Beach
Beachside live music plays most nights on Pensacola Beach, with rotating local acts starting at 5:30 (Sundays 2:30).
/Fri/Sat 5:30 PM · Sun 2:30 PM
18+Wednesdays thru FRI 10/16
Ladies Night: Flora-Bama
Flora-Bama Lounge · Perdido Key
The legendary state-line roadhouse runs Ladies Night every Wednesday 6-9 with free admission, then live music across its stages the rest of the night.
6:00-9:00 PM
Fridays
Pensacola Beach Yoga: Friday and Wednesday beach classes
Pensacola Beach Yoga, beside the Gulf Pier
Pensacola Beach Yoga runs drop-in yoga on the sand beside the Gulf Pier at 41 Fort Pickens Road in Pensacola Beach.
9 AM and Wednesdays 6 PM
THU 10/8–FRI 10/9
Draconid Meteor Shower: the one that happens at bedtime
Your own yard, or Big Lagoon State Park for a darker sky · Pensacola
Nearly every meteor shower asks you to be awake at three in the morning.
From dark, best in the first hours
Thursdays
Civil War Trunk at Fort Pickens
Fort Pickens, Gulf Islands National Seashore · Pensacola Beach
Park rangers open a hands-on Civil War trunk program at Fort Pickens every Thursday afternoon through October 29.
2:00 PM to 4:00 PM
THU 10/8
Perdido Palooza Craft & Vendor Market
Warrior Beer Company · Pensacola
The Perdido Key Area Chamber and Warrior Beer Company run this monthly outdoor market on the second Thursday, with live music, local food trucks, craft beer, and local vendor booths.
5:00 PM to 8:00 PM
21+Every weekend thru FRI 10/16
Weekend Live Music: Sandshaker Lounge
Sandshaker Lounge · Pensacola Beach
The Shaker, birthplace of the Bushwacker, has live music every weekend and never a cover.
Evenings
FRI 10/9
Costa: Pensacola Beach, FL
Laguna's Beach Bar + Grill · Pensacola Beach
Costa takes over Laguna's Beach Bar + Grill on Pensacola Beach for a night that runs from 8 PM to 12:30 AM.
8:00 PM to 12:30 AM
Saturdays thru SAT 10/10
Ocean Hour Beach Cleanup
Rotating, Pensacola Beach / area waterfronts · FL 32561
Give an hour and leave the beach better.
Start time and site posted each week
Sat + Sun thru SUN 10/11
Pensacola Bay Ferry to Fort Pickens
Downtown ferry landing → Fort Pickens → Pensacola Beach
Boat + fort + beach without the car: ranger narration across the bay, tunnels and batteries at Fort Pickens for engineering-minded kids, then the beach stop.
Runs 9 AM-6 PM
SAT 10/10
Santa Rosa Island Triathlon: SOLD OUT (waitlist)
Casino Beach Pavilion · Pensacola Beach
Individual sprint entries are sold out (final tier hit $130).
7:00 AM · Casino Beach
Saturdays
Tailgate in the Tent: Flora-Bama
Flora-Bama: Tent Stage · Perdido Key
Flora-Bama turns its Tent Stage into a game-day sports bar every Saturday through the fall, with a big screen on SEC matchups, live music on two other stages, and a fresh-oyster walk-up bar.
11:00 AM to 6:00 PM
21+SUN 10/11
Flora-Bama Oktoberfest
Flora-Bama · Perdido Key
Flora-Bama throws a family-friendly Oktoberfest each October with a stein-hoisting contest, German food while supplies last, and live polka music from The Brats.
3:00 PM to 6:00 PM
FRI 10/16
Beach-O-Ween 2026
Pensacola Beach Boardwalk
Beach-O-Ween takes over the Pensacola Beach Boardwalk with a bounce house, a costume contest, games, face painting, hotdogs and candy, and Visit Pensacola says every game and activity is…
MON 10/19
Krewe of Wrecks Kick Off Meeting
Bamboo Willie's · FL
Krewe of Wrecks holds its kick off meeting for the season at Bamboo Willie's on Pensacola Beach.
6:00 PM to 7:00 PM
WED 10/21
Annual Multi-Chamber Social 2026
Flora-Bama Main Tent · Perdido Key
The Annual Multi-Chamber Social gathers under the Flora-Bama's Main Tent on Wednesday, October 21, from 5 to 7 PM.
5:00 PM to 7:00 PM CDT
THU 10/22–FRI 10/23
Orionid Meteor Shower: Halley's Comet dust
Your own yard, or Big Lagoon State Park for a darker sky · Pensacola
These are crumbs off Halley's Comet hitting the air at forty-one miles a second.
From 3:15 AM, once the moon is down
FRI 10/23
Cinemas in the Sand: “Toy Story 5”
Gulfside Pavilion, Casino Beach · Pensacola Beach
Toy Story 5 plays free on a giant outdoor screen at the Gulfside Pavilion stage, right on the sand at Casino Beach.
Dusk
SAT 10/24
Witches and Werewolves: Paddle for a Purpose
Hub Stacey's at The Point · Perdido Key
Hub Stacey's at The Point runs a Halloween-themed paddle fundraiser on Saturday, October 24.
Noon to 8:00 PM
MON 10/26
Krewe of Wrecks Halloween Costume Contest
Bamboo Willie's · Pensacola Beach
Krewe of Wrecks runs a Halloween costume contest at Bamboo Willie's on Pensacola Beach.
6:00 PM to 7:00 PM
THU 10/29–SUN 11/1
Taste of the Beach: Pensacola Beach
Casino Beach / beach venues · Pensacola Beach
Saturday is the daylong event at Casino Beach, with cooking demonstrations, challenges and tastings from more than a dozen beach restaurants, and sand for the kids between plates.
Sat daytime = the family window
SAT 10/31
Heron Trot
Big Lagoon State Park · Pensacola
The Heron Trot is a race at Big Lagoon State Park on Saturday, October 31.
7:00 AM
SAT 10/31
Elks Halloween 5K for Elks Charities
Pensacola Beach Elks Lodge 497
Pensacola Beach Elks Lodge 497 runs its second annual Halloween 5K for Elks Charities, and costumes are encouraged.
Start time not published yet
SAT 10/31
Halloween Contest
Flora-Bama · Perdido Key
Flora-Bama runs its annual Halloween costume contest on October 31, right on the state line.
Time not published
THU 11/5–SUN 11/15
Frank Brown International Songwriters' Festival
Flora-Bama Lounge and more than two dozen stages along the Gulf Coast · Perdido Key
More than 200 songwriters play over 600 performances on more than two dozen stages along the Florida and Alabama Gulf Coast during this 11-day festival, which grew out of the Flora-Bama on…
Times vary by stage
THU 11/26
Flora-Bama Thanksgiving Potluck
Flora-Bama Lounge, Package & Oyster Bar · Perdido Key
The Flora-Bama Thanksgiving Potluck is a free community Thanksgiving meal at Flora-Bama Lounge, Package & Oyster Bar, 17401 Perdido Key Dr. The venue provides turkey and ham, and guests…
9:00 AM
SAT 12/5
Flora-Bama Santa Drop
Flora-Bama Lounge, Package & Oyster Bar · Perdido Key
The Flora-Bama Santa Drop is a free holiday event at Flora-Bama Lounge, Package & Oyster Bar, 17401 Perdido Key Dr., where Santa skydives onto the beach at 12:30 PM.
11:00 AM
SAT 12/12
Emerald Coast Ultra
Big Lagoon State Park · Pensacola
The Emerald Coast Ultra is a first-year 50-mile, 50K and relay run along the Gulf shoreline.
5:00 AM
FRI 12/25
Flora-Bama Christmas Potluck
Flora-Bama Lounge, Package & Oyster Bar · Perdido Key
The Flora-Bama Christmas Potluck is a Christmas Day gathering at Flora-Bama Lounge, Package & Oyster Bar, 17401 Perdido Key Dr. Everyone is welcome to bring a side dish while the venue…
Start time not posted
SAT 12/26
Flora-Bama Make It To The Line 4 Mile Run/Walk and 1 Mile Fun Run (39th annual)
Flora-Bama Lounge · Pensacola
Make It To The Line is a 4-mile run or walk and 1-mile fun run starting at the Flora-Bama Lounge on Perdido Key.
9:00 AM
THU 12/31
Flora-Bama New Year's Eve Bash
Flora-Bama Lounge, Package & Oyster Bar · Perdido Key
The Flora-Bama New Year's Eve Bash is a party at Flora-Bama Lounge, Package & Oyster Bar, 17401 Perdido Key Dr., with live music on three stages.
Start time not posted
Open
Fort Pickens · Gulf Islands Seashore
Pensacola Beach
An 1830s fort pairs with a calm sound-side beach, and the rangers run free programs most weeks in season.
Gate 5 AM-8 PM (Mar-Oct) · 5 AM-6 PM (Nov-Feb)
Daily
Big Lagoon State Park
Pensacola
A boardwalk leads to the observation tower, and there is calm lagoon wading and 75 campsites, plus the astronomy club's dark-sky star gazes on scheduled nights.
8 AM to sunset
Open
Glow Paddle: Glow-in-the-Dark Mini Golf
Pensacola Beach (bay side)
9 holes of glow-in-the-dark mini golf on the bay at night, $10 a player, all ages.
By reservation (evening)
Open
Pensacola Beach Gulf Pier: $6.50 Vet Fishing
Pensacola Beach
This spot offers the cheapest real fishing in the radius.
Daily, 24 hours
Open
Charter Fishing: the honest options
Pensacola Beach / Destin
Private option: Heads N Scales inshore, $550 flat for up to 4 (kid-paced; military pricing exists, amount available by phone).
By reservation
Open
Frisky Mermaid Dolphin Cruise
Pensacola Beach
A calm 1.5-2 hr dolphin cruise sails on protected water, the easiest big boat with a baby aboard.
Booking office daily 7 AM-7 PM
Sunrise
Pensacola Beach (Casino Beach)
Pensacola Beach
Classic white-sand day. Quietwater, on the sound side, is calmer for small children.
Sunset
Daily
Johnson Beach · Perdido Key
Perdido Key
A wide, uncrowded national-seashore beach stretches along the Gulf side or the calm sound side.
5 AM-8 PM (Nov-Feb to 6 PM)
Daily
Tarkiln Bayou Preserve State Park
Perdido / SW Pensacola
A boardwalk leads out to a pitcher-plant prairie and quiet bayou overlooks, an easy, cheap nature morning.
8 AM to sunset
Daily
UFO's Mini-Golf, Ice Cream & Arcade
Pensacola Beach
UFO-themed mini golf sits steps from the sand, then ice cream and the arcade, an easy Pensacola Beach add-on.
9 AM-9/10 PM (site inconsistent)
Wed-Thu
Historic Goofy Golf (est. 1958)
W. Pensacola
A retro 1958 landmark course brings dinosaurs, pirates, and campy charm.
10 AM-5 PM · Fri-Sat 10 AM-7 PM · Sun 1-5 PM
Open
Laguna's Adventure Park
Pensacola Beach
This offers beachside ropes, zip rails, go-karts and a splash pad.
Park Thu-Mon 10 AM-8 PM · closed Tue-Wed · watersports daily 9 AM-7 PM
Open
Jolly Sailing & Dolphin/Snorkel Cruise
Pensacola Beach
You can snorkel right off the boat in the shallow Sound, with gear included and dolphins on the way.
By reservation
Open
Run, Roast & Refresh (monthly)
Rotating, Pensacola / Pensacola Beach · check @runroastrefresh
This monthly Saturday wellness social from WHEALTH SOCIAL (RUNCLUB850 and PlungeWorx) has an optional 5K plus 1-mile walk, an iced-latte bar, cold plunges, and yoga and pilates demos.
One Saturday morning a month (date + venue rotate)
Daily
Radical Rides: parasail off Pensacola Beach
Pensacola Beach
Two Ocean Pro 31 winch boats, Coast Guard inspected for 12 passengers, flying single, double and triple, and the doubles and triples go up side by side.
9:00 AM-7:00 PM
Open
Ike's Parasail at the Flora-Bama
Perdido Key · Pensacola
The Perdido Key launch flies off the beach at the Flora-Bama.
9:00 AM-5:00 PM Memorial Day to Labor Day · off-season varies daily
Open
Perdido Key State Park
Pensacola
Perdido Key State Park runs along a barrier island stretch of undeveloped Gulf beach, backed by dunes and sea oats rather than hotels.
8 AM to sunset, 365 days a year.
Monday-Friday
Southwest Library
Pensacola
The Southwest branch, out toward Gulf Beach Highway, runs the same free admission and Monday through Saturday schedule as the rest of the West Florida Public Library system.
10 AM-7 PM; Saturday 10 AM-4 PM; Sunday closed.