This week’s events, in your region, on one page.
Sweet Season Farms Corn Maze & Fall Fun Festival
Sweet Season Farms Corn Maze & Fall Fun Festival at Sweet Season Farms in Milton.
WHO Everyone
WhenSeptember 26–November 8, 2026 · Sat 9 AM-5 PM, Sun 11 AM-5 PM; Fri Oct 23 & 30 6-10 PM
WhereSweet Season Farms, 2260 Horn Rd, Milton, FL 32570
CostSee organizer website for details
Blast on the Bay Songwriters Festival 2026
You can spend four days with 40+ Nashville and rising songwriters in intimate Forgotten Coast venues, anchored by the Party at George Core Park.
WHO Everyone
WhenOct 15–18, 2026 · Contact organizer for hours
WhereMulti-venue Port St. Joe & Forgotten Coast — Party at George Core Park, 162 Miss Zola’s Dr, Port St. Joe, FL 32456
CostSee organizer website for details.
Gallery Night Pensacola — Ghoul-ery Night
You can stroll downtown Gallery Night’s Halloween theme—70+ art vendors, live performances and food trucks on a free Friday evening presented with Publix.
WHO Family
WhenFri Oct 16, 2026, 5:00–9:00 p.m.
WhereDowntown Pensacola Gallery Night footprint, 13 Palafox Place, Pensacola, FL 32502
CostFREE.
Panama City Beach Oktoberfest 2026
Three days at Aaron Bessant Park in a Munich-style tent with German and craft beer, live music by The Bräts, The Czechers and the Will Thompson Band, bounce houses and face painting—kids 12 and under free on GA.
WHO Family
WhenFri Oct 16, 2026, 4:00–11:00 p.m.; Sat Oct 17, 12:00–11:00 p.m.; Sun Oct 18, 12:00–5:00 p.m.
WhereAaron Bessant Park, 500 West Park Drive, Panama City Beach, FL 32413
Cost3-day General Admission tickets start at $20 ahead of time; FREE for kids 12 and under.
Goat Day & Pioneer Day
Goat Day arts and crafts land next to Pioneer Day living history at Panhandle Pioneer Settlement — $5 cash covers both.
WHO Family
WhenSat Oct 17 · gates open 8:00 AM CT
WherePanhandle Pioneer Settlement inside Sam Atkins Park, 17869 NW Pioneer Settlement Road, Blountstown (Calhoun)
Cost$5 adults (cash) · ages 3 & under free
Paws in the Park
Bring family, friends and pets to Frank Brown Park Dog Park for Police K9 demonstrations, a Doggie Dash with medals, an adoption booth and a pet costume contest.
WHO Family
WhenSat Oct 17, 2026, 9:00 a.m.–12:00 p.m.
WhereFrank Brown Park Dog Park, 16200 Panama City Beach Parkway, Panama City Beach, FL 32413
CostFREE.
30th Annual Holiday Decorating Showcase
Chipley Woman’s Club brings Kirby Holt AIFD and Brad Holt for Christmas tree and floral demos at 10 AM and 6 PM.
WHO Everyone
WhenThu Oct 22 · shows 10:00 AM and 6:00 PM
WhereWashington County Ag Center, 1424 Jackson Avenue, Chipley (Washington)
Cost$20 per person
Pensacola Hippie Fest 2026 (SevilleStock)
A free SevilleStock day under the oaks—artisan marketplace, vintage market, food trucks, Family Fun Zone and a classic & vintage car show at Bartram Park.
WHO Family
WhenSat Oct 24, 2026, 10:00 a.m.–6:00 p.m.
WhereSeville Square, Fountain Park & Bartram Park, 331 East Government Street, Pensacola, FL 32502
CostFREE.
2nd Annual Destin Songwriter Festival
You can hear Nashville hit songwriters across Destin Harbor—free side stages all weekend, ticketed Main Stage in front of SkyBar at The Edge, and VIP Sunday at The Alice.
WHO Everyone
WhenOct 24–25, 2026 · Contact organizer for hours
WhereMulti-venue Destin Harbor — Main Stage in front of SkyBar at The Edge / Edge Seafood, 302 Harbor Blvd, Destin, FL 32541
CostSee organizer website for details.
Mattie Kelly Festival of the Arts
Mattie Kelly’s 31st Festival of the Arts brings 100+ juried artists to the Dugas Pavilion Green — admission and parking free.
WHO Family
WhenSat Oct 24–Sun Oct 25. Sat 9:00 a.m.–5:00 p.m.; Sun 10:00 a.m.–4:00 p.m.
WhereMattie Kelly Dugas Pavilion Green, 4323 Commons Dr W, Destin (Okaloosa County)
CostFREE
City of Destin's 26th Annual Fall Festival
City of Destin’s Fall Festival packs the Community Center with games, a cakewalk, costume contest, and a non-perishable food ask at the gate.
WHO Family
WhenMon Oct 26. 5:00 PM – 8:00 PM
WhereDestin Community Center, 101 Stahlman Ave, Destin (Okaloosa County)
CostBring one non-perishable food item for admission
Great Gulfcoast Arts Festival
Juried fine arts fill Seville Square with 200+ artists, Heritage Arts, music stages, and a Children’s Art Festival in Bartram Park.
WHO Family
WhenFri Nov 6–Sun Nov 8. Fri–Sat 9:00 a.m.–5:00 p.m.; Sun 9:00 a.m.–4:00 p.m.
WhereSeville Square, 301 South Alcaniz St, Pensacola (Escambia County)
CostFREE
Pensacola Greek Festival (66th Annual)
Pensacola's 66th Annual Greek Festival returns to Annunciation Greek Orthodox Church.
WHO Family
WhenFri Nov 6–Sun Nov 8 · Contact organizer for hours
WhereAnnunciation Greek Orthodox Church, 1720 West Garden Street, Pensacola (Escambia)
CostSee organizer website for details
Festa Italiana
Festa Italiana at Fountain Park in Pensacola.
WHO Everyone
WhenNovember 13–14, 2026 · 11 AM – 6 PM
WhereFountain Park, 300 E Zaragoza St, Pensacola, FL 32502
CostSee organizer website for details
Forgotten Coast Festival of Trees
Joe Center’s Forgotten Coast Festival of Trees turns the Reid Avenue gallery into decorated trees, wreaths, and a silent auction through Dec 12.
WHO Everyone
WhenFri Nov 20–Sat Dec 12 · Contact organizer for daily gallery hours (Opening Reception Fri Nov 20; silent auction through Dec 10)
WhereThe Joe Center for the Arts, 201 Reid Avenue, Port St. Joe (Gulf)
CostSee organizer website for details
Lynn Haven Winter Wonderland
Lynn Haven Winter Wonderland packs the Sports Complex with vendors, Mrs. Claus story time, crafts, and food trucks.
WHO Family
WhenSat Nov 21 · 9:00 AM–3:00 PM
WhereLynn Haven Sports Complex, 2201 Recreation Drive, Lynn Haven (Bay)
CostSee organizer website for details
Creek Fest '26
Santa Rosa Band of the Lower Muscogee brings pow wow drum, Creek village, and the Battle of Chumuckla reenactment across two days.
WHO Family
WhenSat Nov 21–Sun Nov 22 · 9:00 AM–6:00 PM each day
WhereSanta Rosa County Creek Indian Tribal Grounds, 4750 Willard Norris Road, Milton (Santa Rosa)
Cost$5 general · kids under 7 free · parking free