Clearwater packed its fall calendar with more than a dozen free and low-cost events running through late November, the city announced in its official fall events roundup on Tuesday, Sept. 29.

Opening weekend brings festivals and fishing

The season opens Friday, Oct. 2, with the Countryside Family Fall Fest at Countryside Recreation Center, 5:30 to 8:30 p.m. Admission is $4 with pre-registration or $6 at the door for ages 2 to 18; adults and children under 2 get in free.

Saturday, Oct. 3, brings two events. The Fall Y'all Festival takes over Coachman Park, 300 Cleveland St., from 11 a.m. to 5 p.m. with food trucks, local vendors, a Kids Zone and a Lil Miss & Sir Pumpkin Contest. Admission is free. That same morning, the Make a Difference Fishing Tournament for Kids runs 8 a.m. to 1 p.m. at Pier 60 Park, 370 Mandalay Ave. The nonprofit organizes fishing programs for children and adults with disabilities.

Halloween events pack the October calendar

October is loaded with Halloween options. The North Greenwood Bootacular Trunk or Treat follows on Oct. 8, 5 to 7 p.m. at North Greenwood Library, free. Two events share Oct. 16: the Glow and Boo Bash at The Long Center, 5:30 to 8:30 p.m. ($7 per person, ages 3 and up), and the Halloween JuBOOlee at Morningside Recreation Center, 5:30 to 8:30 p.m. ($3 per person).

On Oct. 24, Owl-O-Ween at Moccasin Lake Nature Park offers $2 admission from 3 to 7 p.m. That evening, the Clearwater Urban Leadership Coalition hosts a free Community Family Fun Night at Buccaneer Field, Walter C. Campbell Park, with line dancing, salsa dancing, games and bounce houses from 4:30 to 9:30 p.m.

The month's two biggest Halloween events close out the final weekend. Fall-O-Ween fills Coachman Park on Oct. 30 from 6 to 10 p.m. with a costume contest, candy trail, food trucks, a Carrie Underwood tribute band called Carnival Ride, touch-a-truck and Dino Dig. It's free. The Ross Norton Trunk or Treat also runs that evening, 5 to 7 p.m., free.

On Oct. 31, the city of Clearwater and the Clearwater Threshers co-host Boo Bash at BayCare Ballpark, 601 Old Coachman Road, from 5 to 8 p.m. Families walk table to table on the concourse, collecting candy from more than 25 stations set up by local businesses. The event also features hayrides, games and a costume parade. Admission is free.

The Clearwater Jazz Holiday, now in its 47th year, runs Oct. 15-18 at Coachman Park. Coverage of that festival is forthcoming separately.

Turkey Trot, tree lighting close out November

Looking ahead to November, the Make a Difference Fishing Tournament for Adults takes place Nov. 7 at Pier 60 Park from 8 a.m. to 1 p.m.

The 2026 Achieva Clearwater Turkey Trot takes place Thanksgiving morning, Nov. 26, at Clearwater High School, 1951 Gulf to Bay Blvd. The city calls it one of Tampa Bay's longest-running Thanksgiving traditions. Three race options start between 7 and 9:15 a.m.: the Achieva 5K Timed Run at 7 a.m., the FrankCrum Family Fun 5K at 8 a.m. (strollers and leashed dogs welcome) and the Abe's Place 1-Mile Drum Run at 9:15 a.m. Every registered participant receives a collectible 2026 medal. Registration is open at RunSignUp.com.

Packet pickup runs at Achieva Credit Union headquarters in Dunedin on Nov. 21 from 2 to 6 p.m. and at the Clearwater branch, 2201 Drew St., on Nov. 23 from 5:30 to 8:30 p.m. A Pre-Trot Community Celebration at BayCare Ballpark on Nov. 25 from 4 to 8 p.m. features live music, giveaways and street performers. Race-morning road closures will affect Gulf to Bay Boulevard, Keene Road, Hercules Avenue, Druid Road and surrounding streets.

The season wraps with Clearwater's Bright and Beautiful Tree Lighting on Nov. 29 from 5 to 9 p.m. at Coachman Park. The free event features Christmas carolers, a snow machine, inflatables, dance groups, food trucks and photos with Mr. and Mrs. Claus.

For details on any city event, contact Clearwater Special Events at 727-562-4700 or [email protected].