[Clearwater Jazz Holiday in Coachman Park | 2025]
Pinellas County is gearing up for a busy stretch of fall events, and there's something happening nearly every weekend from Clearwater down through Dunedin, Palm Harbor, and Safety Harbor. Whether you're into live music, street festivals, art markets, or family-friendly carnivals, here's a roundup of what's on the calendar this September, October, and into November 2026.
Clearwater
Clearwater's Coachman Park and The BayCare Sound continue to be the epicenter of live music in the region this fall. September brings a stacked concert lineup, including the 97X Next Big Thing Legends show with Yellowcard and Waterparks, Modest Mouse, W.A.S.P. & KK's Priest at Ruth Eckerd Hall, and a big John Fogerty and Steve Winwood run of shows. Rock band America kicks off October with its "Happy Trails Tour" stop in town.
The city's marquee music event, the Clearwater Jazz Holiday, returns October 15–18, 2026 at Coachman Park for its 47th year, drawing music lovers from across Tampa Bay for four days of jazz, funk, and soul on the waterfront. The Clearwater Marine Aquarium also keeps a steady stream of community programming going, including monthly Lake Belleview cleanups with its Sea Turtle Conservation Program.
Dunedin
Dunedin's small-town charm is on full display this season. The Dunedin Downtown Market runs regularly on Main Street, and the town has a full slate of only-in-Dunedin happenings, including the 4th Annual Downtown Dunedin Mocktail Walk, a World Car Free Day celebration, and beach cleanups at Honeymoon Island with Salty Soul. Live music fans can catch acts at Dunedin House of Beer and the Captain's Lounge yacht rock series.
Looking ahead, Island Fest takes over the causeway on October 10, and outdoorsy types will want to save December 5 for the Honeymoon Island Bluegrass Festival. Sports fans can also catch Dunedin Blue Jays games at TD Ballpark throughout the fall schedule.
Palm Harbor
Palm Harbor's community calendar is anchored by its beloved First Friday celebrations at Pop Stansell Park, which bring rides, games, local vendors, and live music to downtown each month — the next one falls on September 19. October brings the annual Taste of Palm Harbor, a seafood-and-live-music staple, along with the Halloween Carnival on October 30 at White Chapel and Harbor Hall, complete with a haunted chapel, hayride, and trick-or-treat trail for the kids.
The Palm Harbor Museum's Wine Around Palm Harbor fundraiser is set for November 7, and Palm Harbor Parks & Recreation has a Touch-a-Truck event and holiday tree lighting already on the books for later in the season.
Safety Harbor
Safety Harbor keeps its small-town social calendar humming with the long-running 3rd Friday Street Celebration, a free, dog-friendly street festival that closes nine blocks of Main Street for live music, artisan vendors, and open patios from 6–10 p.m. The next dates are September 18 and October 16, 2026.
The city also just marked a milestone with the reopening and ribbon-cutting of the Fire Marshal Dick Brock Memorial Pier on September 12, rebuilt after storm damage from the 2024 hurricane season — a nice one for a sunset stroll. Other community happenings include Pickin' in the Park at the Folly Farm Gazebo and the Folly Faire at Folly Farm Nature Preserve.
Plan Your Fall Around Pinellas County
From jazz on the Clearwater waterfront to street festivals in Safety Harbor and family carnivals in Palm Harbor, Pinellas County's fall calendar has something for everyone. Most of these events are free or low-cost, family-friendly, and a great way to support the small businesses that make each of these communities feel like home. Grab a friend, check the exact dates before you go (community calendars do shift), and get out and enjoy everything this corner of the Gulf Coast has to offer this season.
Event dates are subject to change — always confirm details with the host city or venue before heading out.