Lyrics on the Harbor: Destin’s First Songwriter Festival
October 10–11, 2025 | Heron Harbor, Destin, Florida
For the first time, Destin Harbor will echo with the stories behind the songs you love. The inaugural Destin Songwriter Festival transforms Heron Harbor (314 Harbor Blvd.) into two days of music, storytelling and coastal beauty.
Enjoy free daytime shows on three harbor-front stages, then ticketed evening headliners on the Main Stage. Acclaimed songwriters from across the country will share acoustic sets and the inspiration behind their hits, creating an unforgettable waterfront experience.
Tickets & Details: GA 2-Day Pass: $60 | GA Friday or Saturday: $35/day | VIP Table (2-Day): $1,000. Main Stage shows require GA or VIP tickets; side stages are free.
A portion of proceeds supports Operation Song, a nonprofit helping veterans and military families heal through songwriting.
Tickets: DestinSongwritersFestival.com
Annual Bloody Mary Festival
Saturday, Oct. 11 | 11 a.m.–2 p.m. | The Market Shops, Miramar Beach
Sip and savor creative Bloody Marys from area restaurants, bars and resorts at this popular and colorful fall festival, with live music, a photo booth and local vendors. Proceeds benefit Habitat for Humanity of Walton County.
Tickets & details: thebloodymaryfest.com
Harvest Wine & Food Festival
Oct. 16–19 | Times vary by event | Cerulean Park, WaterColor
Four days. World-class wine. Unforgettable food. From Friday’s sultry Harvest After Dark to Saturday’s legendary Grand Tasting and elegant Sunday brunch, this is one of the Southeast’s premier festivals. Proceeds benefit Destin Charity Wine Auction Foundation.
Tickets and details: dcwaf.org
Fall Silent Auction for Emerald Coast Food Rescue
Friday, Oct. 24 | 6–9:30 p.m. | Local Market, Destin
Bid for a cause! Help fight hunger in Okaloosa and Walton counties while enjoying food, drinks and community fun. Proceeds support ECFR’s mission to deliver 250,000 pounds of food monthly.
Details: emeraldcoastfoodrescue.org
Fleets and Eats: A Party for a Purpose
Saturday, Oct. 25 | 6 p.m. | Destin Harbor (Tailfins, The Edge, Harbor Docks)
Hop aboard tiki boats for a Lu’au-style harbor crawl with cocktails, hors d’oeuvres, and live music. Proceeds support autism services at ECAC. Afterparty at Tailfins!
Tickets & Details: ecautismcenter.org
Barktoberfest
Thursday, Oct. 30 | 4:30–6:30 p.m. | Grand Park, Grand Boulevard at Sandestin
Paws down, the cutest fall fest around! Bring your pup in costume for trick-or-treating, a legendary doggie costume contest, live DJ, photo booth, and tasty bites. $15 preregistration ($20 day-of). Benefits Dog-Harmony.
Register: dog-harmony.org
Escape to Wonderland Halloween Party
Friday, Oct. 31 | 6–11 p.m. | Ara Rooftop Pool & Lounge, Hotel Effie Sandestin
Sip, dance, and play croquet with the Queen of Hearts at this Alice in Wonderland–themed rooftop party. DJ, costume contest, themed bites, and cocktails. Tickets $35.
Info: hoteleffie.com
Trick or Treat Street
Friday, Oct. 31 | 6–8 p.m. | The Village of Baytowne Wharf, Sandestin
Ghosts, ghouls, and goblins take over Baytowne! Trick-or-treat at merchant booths, enjoy live music, and don’t miss the fireworks at 8 p.m. Free admission.
Details: baytownewharf.com
11th Annual Eggs on the Beach – Big Green Egg Cooking Competition!
Saturday, Nov. 1 | 10 a.m.–1 p.m. | Seascape Resort, Miramar Beach
Big Green Egg fans unite! Sample unlimited bites from 20+ cook teams, including nine nonprofits, and cast your votes for the 2025 People’s Choice Awards. A distinguished panel of judges features local chefs, Big Green Egg grill masters, and celebrity talent from Netflix and Food Network. Hosted by Bay Breeze Patio, this fan-favorite foodie fest benefits Fisher House of the Emerald Coast and Food For Thought.
Tickets & details: EggsOnTheBeach.com
Pirate Brew Fest
Saturday, Nov. 1 | 11 a.m.–3 p.m. | Fudpucker’s, Destin | FREE Admission
Ahoy, mateys! Fudpucker’s hosts the Pirate Brew Fest, a lively afternoon of food, fun, and frothy brews. Enjoy live music, games, artists and vendors, alcohol samples, and a pirate costume contest. Festivities also include a magician, mermaid, fire performer, and beer memorabilia on display. Pirate attire is encouraged—and the first 100 pirates through the gate will receive special gifts. Admission is free.
Details: PirateBrewFest.com
Decades On Display: A Nostalgic Journey Through Automotive History Past & Current
Saturday, Nov. 1 | 10 a.m. | Heritage Museum | Valparaiso, 115 Westview Ave. | FREE Admission
Join the Heritage Museum for Decades On Display. Take a ride through time with iconic cars from the swinging ’60s to the bold ’80s and beyond! This family-friendly event promises fun, flair and plenty of photo-worthy moments. To enter a vehicle: GA: $35 | VIP: $40 (limited availability)
Info: 850-678-2615
27th Annual Pinfish Classic – Destin
Saturday, Nov. 1 | 7–9 a.m. | Dock behind AJ’s, 116 Harbor Blvd., Destin
The City of Destin hosts its annual catch-and-release Pinfish Classic for kids ages 14 and under. Bring your own pole—bait is provided! Awards will be given for the largest, smallest and most fish caught in each age group, with prizes announced at 8:45 a.m. Free family-friendly fun on the Harbor.
Details: cityofdestin.com/reconline
SOWAL Jazz Fest
Nov. 6–8 | Times vary by venue | Along Scenic Highway 30A
A cool new tradition debuts! Three nights of intimate jazz at local venues, with tributes to Sinatra, Billie Holiday, Amy Winehouse, and more. Tickets start at $50.
Tickets: sowaljazzfest.com
Animoré – Weekend of Compassion for Animals
Alaqua Animal Refuge | Freeport
9th Annual 100 Point + Cult Wine Dinner | Friday, Nov. 7 | 5 p.m.
Festivities at the exclusive 9th Annual 100 Point + Cult Wine Dinner are limited to 100 guests. Enjoy a cocktail reception, a four-course dinner by Café Thirty-A paired with rare 100-point wines, and a private dressage performance by USDF medalist Jodie Kelly. The evening also features a live auction with unforgettable trips to Italy, Iceland, and more. Tickets: $1,250 per guest.
Bluegrass Barn Jam & Fall Fest | Saturday, Nov. 8 | 11 a.m.-6 p.m.
Saturday’s Bluegrass Barn Jam & Fall Fest is a vibrant day of live music, local fare, and family fun in support of Alaqua’s life-saving mission. Proceeds benefit Alaqua’s mission to provide shelter, safety and second chances to animals in need.
Tickets & details: alaqua.org (Friday’s dinner ticket includes VIP admission to Bluegrass Barn Jam.)
30A BBQ Festival – 10 Years of Sizzling Flavor!
Friday, Nov. 7 | 5–8 p.m. | Grand Boulevard, Miramar Beach
The 6th Annual 30A BBQ Festival, presented by 360 Blue, serves up all-you-can-eat barbecue, live music by River Dan, drinks, a silent auction, and more—all benefiting The Sonder Project’s 10th anniversary.
GA: $60 | VIP: $125 | Kids 12 & under free
Tickets: bit.ly/30a-bbq-2025 | Sponsorships: jessica@proffittpr.com
33rd Annual Flutterby Arts Festival
Sunday, Nov. 9 | 10 a.m.–4 p.m. | Watersound Town Center
Celebrate creativity and the Monarch migration with a full day of fun for all ages! Enjoy hands-on art activities, student exhibits, live performances, an artist market and the beloved butterfly parade. Free and family-friendly.
Details: culturalartsalliance.com
