October 6
Wellness By The Water Yoga | 8:30am | The Alice Destin
Mug Club & Bingo | 6pm | Destin Brewery
Karaoke | 6pm | AJ’s on the Bayou
Karaoke | 6pm-9pm | Fatboys Destin
Trivia Night | 6pm | Rick’s Crab Trap | Okaloosa Island
Columbus Day Weekend Movie on the Beach | 8pm | The Boardwalk | Okaloosa Island
October 7
Collab & Co-Working w/ Women in Business | 1pm | Coastal Protein & Energy
Bonfire on the Beach | 5pm | The Bay | SRB
Trivia Night | 5pm | Down Island | SRB
Run Club | 5:30pm | Destin Brewery
Trivia Night | 6pm | Destin Brewery
Trivia Night | 6pm | Craft Bar @ The Harbor
Karaoke | 7pm | Kenny D’s
Karaoke | 7pm | AJ’s Oyster Shanty
Columbus Day Weekend Karaoke | 7–10pm | The Boardwalk | Okaloosa Island
October 8
Sinfonia Gulf Coast’s Cabaret | 5:30pm | Seagar’s Prime Steaks & Seafood | Miramar Beach
Little Black Dress Night | 6:30pm-9:30pm | Marina Café
Fort Comedy Open Mic Standup | 7pm | Downtown Music Hall | FWB
Karaoke Night | 9pm | Harry T’s Lighthouse
Ladies Night | 10pm | McGuire’s Destin
October 8–10
Rockin’ in Paradise with Styx & Friends | 3–10pm daily | Seascape Resort | Miramar Beach
October 9
Friday Martini Lunch | 11am-4pm | Skybar Destin
Special 250th History Sandwiched In Lunch | Noon | Heritage Museum of NWFL | Val’p
Free Beach Bonfire | 5pm | Royal Palm Grille
Movies on the Lawn: Fall Edition | 6pm | Harborwalk Village
Karaoke | 7pm | Island Wing Company
Salsa & Bachata Dance Lessons | 8pm | Bric a Brac | Destin
Latin Night | 8pm-2am | Bosforo | Miramar Beach
Karaoke | 8pm | Harry T’s Lighthouse
October 10
Emerald Coat Home & Boat Show! | 10am-5pm | Destin FWB Convention Center
Yoga with Dolphins | 7:30am | Gulfarium Marine Adventure Park
Famers Market | 9am-1pm | Grand Blvd | SRB
Farmers Market | 9am | Seaside, FL
America 250 Heritage Festival & Scouting Expo | 9am | Destin-Fort Walton Beach Rigdon Center | FWB
Bloody Mary Festival | 10am | The Market Shops | Miramar Beach
Nautical Flea Market | 10am–2pm | LJ Schooner’s | Bluewater Bay
Saturday Sing-A-Long Brunch | 11:30am | Skybar Destin
Dogs, Bands & Beer Festival | Bands start 1:30pm | Mattie Kelly Arts Center | Niceville
Rocktober Concert Series | 5pm | Harborwalk Village
Sip n Shop: Fall Edition | 5pm | Harborwalk Village
Karaoke | 6pm | Fatboys Destin
Fireworks on the Harbor | 8pm | Harborwalk Village
Karaoke | 8pm | Harry T’s Lighthouse
Karaoke | 9pm | Fubar | Okaloosa Island
October 11
Emerald Coat Home & Boat Show | 10am-3pm | Destin FWB Convention Center
Sunrise Sculpt on the Harbor | 6:30am | Happy Life Cruises | Destin
DJ Brunch | 10am | Azul @ Harborwalk | Destin
Columbus Day Weekend Karaoke | 7–10pm | The Boardwalk | Okaloosa Island
Columbus Day Weekend Fireworks Show | 9pm | The Boardwalk | Okaloosa Island
Karaoke | 9pm | Fubar | Okaloosa Island
Karaoke | 9pm | Outcast Bar & Grill | SRB
October 12
Free Beach Bonfire/SIN Night | 5pm | Royal Palm Grille
Bingo Night | 6pm | American Legion Destin, 311 Main St
October 13
Wellness By The Water Yoga | 8:30am | The Alice
Mug Club & Bingo | 6pm | Destin Brewery
Karaoke | 6pm | AJ’s on the Bayou
Karaoke | 6pm-9pm | Fatboys Destin
Trivia Night | 6pm | Rick’s Crab Trap | Okaloosa Island
October 14
Pilates with Dolphins | 7:30am | Gulfarium Marine Adventure Park
Trivia Night | 5pm | Down Island | SRB
Run Club | 5:30pm | Destin Brewery
Trivia Night | 6pm | Destin Brewery
Trivia Night | 6pm | Craft Bar @ The Harbor
Karaoke | 7pm | Kenny D’s
Karaoke | 7pm | AJ’s Oyster Shanty
October 15
Bubbly Baytowne | 5pm | Baytowne Wharf | Sandestin
Harvest Wine Dinners | 6pm-9pm | Various Locations
Little Black Dress Night | 6:30pm-9:30pm | Marina Café
Fort Comedy Open Mic Standup | 7pm | Downtown Music Hall | FWB
Karaoke Night | 9pm | Harry T’s Lighthouse
Ladies Night | 10pm | McGuire’s Destin
October 15-25
Emerald Coast Theatre Co.’s The 39 Steps | Times vary | Grand Blvd | Sandestin
October 16
Friday Martini Lunch | 11am-4pm | Skybar Destin
Free Beach Bonfire | 5pm | Royal Palm Grille
Mayor’s Charity Gala | 5:30pm | The Henderson | Destin
Movies on the Lawn: Fall Edition | 6pm | Harborwalk Village
Baytowne Beer Festival | 6pm-9pm | Baytowne Wharf | Sandestin
ADSO’s Celebrate Autumn Art Exhibition Opening Reception | 6–8 pm | Arts and Design Society, 17 First Street SE | FWB
Exhibition Dates | Oct. 13–Nov.7 | Tues–Fri: 12–4 pm; Sat: 1–4 pm
Karaoke | 7pm | Island Wing Co
Harvest After Dark | 7pm-10pm | Cerulean Park, Watercolor
Salsa & Bachata Dance Lessons | 8pm | Bric a Brac
Latin Night | 8pm-2am | Bosforo in Miramar Beach
Karaoke | 8pm | Harry T’s Lighthouse
Karaoke | 8pm | 5 o’Clock Somewhere | Baytowne Wharf
October 16-17
McCaskill & Company’s First-Ever Men’s Weekend | 10am – 5:30pm | McCaskill & Company | Destin
October 17
Pilates with Dolphins | 7:30am | Gulfarium Marine Adventure Park
Pumpkin Festival | Hammock Bay | Freeport
Famers Market | 9am-1pm | Grand Blvd
Farmers Market | 9am | Seaside, FL
Saturday Sing-A-Long Brunch | 11:30am | Skybar Destin
Harvest Food & Wine Grand Tasting | 1pm | Cerulean Park, Watercolor
Baytowne Beer Festival Grand Tasting | 2pm | Baytowne Wharf | Sandestin
Rocktober Concert Series | 5pm | Harborwalk Village
Black Cat Ball | 6pm | Elks Lodge | Okaloosa Island
Karaoke | 6pm | Fatboys Destin
Sinfonia Gulf Coast’s The Wizard of Oz: Film in Concert | 7pm | Mattie Kelly Arts Foundation Dugas Pavilion | Destin
Fireworks | 8pm | Harborwalk Village
Karaoke | 8pm | Harry T’s Lighthouse
Karaoke | 9pm | Fubar | Okaloosa Island
October 18
Pumpkin Festival | Hammock Bay | Freeport
Back-to-School Rock Painting Party | 9-11 a.m. | Captain Royal Melvin Heritage Park
DJ Brunch | 10am | Azul @ Harborwalk
Jazz Cocktail Brunch (Harvest Food & Wine) | 11am | 140 Flatwood St | WaterColor SRB
Karaoke | 9pm | Fubar
Karaoke | 9pm | Outcast Bar & Grill
October 19
Free Beach Bonfire/SIN Night | 5pm | Royal Palm Grille
Bingo Night | 6pm | American Legion Destin, 311 Main St
October 20
Wellness By The Water Yoga | 9am | The Alice Destin
A Superior First Responders Appreciation Lunch | 11:30am–1pm | Niceville Community Center
Mug Club & Bingo | 6pm | Destin Brewery
Karaoke | 6pm | AJ’s on the Bayou
Karaoke | 6pm-9pm | Fatboys Destin
Trivia Night | 6pm | Rick’s Crab Trap | Okaloosa Island
October 21
Bonfire on the Beach | 5pm | The Bay | SRB
Run Club | 5:30pm | Destin Brewery
Trivia Night | 6pm | Destin Brewery
Trivia Night | 6pm | Craft Bar @ The Harbor
Karaoke | 7pm | Kenny D’s | Destin
Karaoke | 7pm | AJ’s Oyster Shanty
October 22
All Sports Association Presents Casino Night | 5pm | Destin FWB Convention Center
Business After Hours | 5:30pm | Beachworx
Little Black Dress Night | 6:30pm-9:30pm | Marina Café
Fort Comedy Open Mic Standup | 7pm | Downtown Music Hall
Karaoke Night | 9pm | Harry T’s Lighthouse
Ladies Night | 10pm | McGuire’s | Destin
October 23
Friday Martini Lunch | 11am-4pm | Skybar | Destin
Free Beach Bonfire | 5pm | Royal Palm Grille | Destin
Movies on the Lawn: Fall Edition | 6pm | Harborwalk Village
Karaoke | 7pm | Island Wing Company | Destin
Salsa & Bachata Dance Lessons | 8pm | Bric a Brac
Latin Night | 8pm-2am | Bosforo | Miramar Beach
Karaoke | 8pm | Harry T’s Lighthouse
October 23–25
Shinedown’s Lunatic Ball Beach Weekend | 3pm daily | Seascape Resort
October 24
Yoga with Dolphins | 7:30am | Gulfarium Marine Adventure Park
McGuire’s Halloween Run | 9am-Noon | Destin
Famers Market | 9am-1pm | Grand Boulevard | SRB
Farmers Market | 9am | Seaside, FL
Destin Songwriter Festival | 12pm-8pm | Destin Harbor
Halloween Spooktacular | 3pm | Harborwalk Village
Jeepalooza Parade Invasion 2026 | 5pm | John Beasley Park | Okaloosa Island
Rocktober Concert Series | 5pm | Harborwalk Village
Movies on the Lawn: Fall Edition | 6pm | Harborwalk Village
Karaoke | 6pm | Fatboys | Destin
Fireworks | 8pm | Harborwalk Village
Karaoke | 8pm | Harry T’s Lighthouse | Destin
Karaoke | 9pm | Fubar | Okaloosa Island
October 24–25
31st Annual Festival of the Arts | 9am–5pm Sat; 10 am–4 pm Sun | Cultural Arts Village | Destin
October 25
DJ Brunch | 10am | Azul @ Harborwalk Village
3rd Annual OKI Fest | 11am | 1958 Lewis Turner Blvd | FWB
Destin Songwriter Festival | 12pm-8pm | Destin Harbor + The Alice
Halloween Haunt | 6-8pm | Destin Commons
Karaoke | 9pm | Fubar | Okaloosa Island
Karaoke | 9pm | Outcast Bar & Grill | SRB
October 26
26th Annual Destin Fall Festival | 5-8 p.m. | Destin Community Center
The Next BIG Thing 2026 | 8am – 5pm | Hilton Sandestin Beach | Miramar Beach
Free Beach Bonfire/SIN Night | 5pm | Royal Palm Grille
Bingo Night | 6pm | American Legion, 311 Main St | Destin
October 27
Wellness By The Water Yoga | 9am | The Alice Destin
Mug Club & Bingo | 6pm | Destin Brewery
Karaoke | 6pm | AJ’s on the Bayou
Karaoke | 6pm-9pm | Fatboys Destin
Trivia Night | 6pm | Rick’s Crab Trap | Okaloosa Island
October 28
Pilates with Dolphins | 7:30am | Gulfarium Marine Adventure Park
Bonfire on the Beach | 5pm | The Bay | SRB
Run Club | 5:30pm | Destin Brewery
Trivia Night | 6pm | Destin Brewery
Trivia Night | 6pm | Craft Bar @ The Destin Harbor
Karaoke | 7pm | Kenny D’s
Karaoke | 7pm | AJ’s Oyster Shanty
October 29
Wellness By The Water Yoga + Mini Massages | 8:30am | The Alice Destin
Business After Hours | 5:30pm | Beachworx
Little Black Dress Night | 6:30pm-9:30pm | Marina Café
Fort Comedy Open Mic Standup | 7pm | Downtown Music Hall | FWB
Karaoke Night | 9pm | Harry T’s Lighthouse
Ladies Night | 10pm | McGuire’s Destin
October 30
Friday Martini Lunch | 11am-4pm | Skybar Destin
Dog-Harmony’s 11th Annual Barktoberfest | 4:30–6:30pm | Grand Blvd | Sandestin
Free Beach Bonfire | 5pm | Royal Palm Grille
Halloween Eve Fun with Ron Adams | 6pm | Tuscany Italian Bistro
Movies on the Lawn: Fall Edition | 6pm | Harborwalk Village
Karaoke | 7pm | Island Wing Co
Salsa & Bachata Dance Lessons | 8pm | Bric a Brac | Destin
Latin Night | 8pm-2am | Bosforo | Miramar Beach
Karaoke | 8pm | Harry T’s Lighthouse
October 31
Pilates with Dolphins | 7:30am | Gulfarium Marine Adventure Park
Famers Market | 9am-1pm | Grand Blvd | SRB
Farmers Market | 9am | Seaside, FL
Karaoke | 6pm | Fatboys Destin
Breaking Through the Decades — A Halloween Extravaganza | 6-11pm | Ara Rooftop
Fireworks | 8pm | Harborwalk Village
Karaoke | 8pm | Harry T’s Lighthouse
Karaoke | 9pm | Fubar | Okaloosa Island
