#1 John’s Pass Seafood Festival
Fresh Gulf seafood, live music and Halloween fun take over John’s Pass Village Friday–Sunday, October 23–25, for the 45th Annual John’s Pass Seafood Festival! Browse local arts and crafts vendors, enjoy waterfront dining and catch live entertainment throughout the weekend. Friday brings family-friendly trick-or-treating through the Village, while Saturday’s Costume Contest and Block Party runs from 6–9pm, with creative costumes, live music and cash prizes. Admission is free!
Learn more at https://www.paradisenewsfl.com/45th-annual-johns-pass-seafood-festival/.
#2 Cheer on Your Rays
It’s time to cheer on your Tampa Bay Rays in game 1 of the World Series! The Rays take on the Milwaukee Brewers in Game 1 of the World Series this Friday, October 23rd 8pm, and Pinellas County has plenty of places to watch the action with fellow fans. From Ferg’s in St. Pete to waterfront favorites and beach-town pubs, we’ve rounded up nine local spots to watch the World Series, grab a bite and celebrate every big play. Go Rays!
Find our picks for where to watch your Tampa Bay Rays at https://www.paradisenewsfl.com/rays-up-2026/.
#3 Halloween on Central
Get ready for a full day of Halloween fun as Halloween on Central returns Sunday, October 25th, transforming 22 blocks of Central Avenue across St. Pete’s Edge and Grand Central districts into a massive, car-free street festival! Dress up and explore live music, local vendors, immersive experiences, family-friendly activities and plenty of candy. With entertainment for all ages and thousands of costumed revelers, this free-spirited community celebration is one of St. Pete’s biggest Halloween traditions!
Learn more at https://www.grandcentraldistrict.org/halloween-on-central/.
#4 TFO Pops in the Park
Pack a picnic, bring a blanket and enjoy free music under the stars at TFO’s Pops in the Park this Sunday, October 25th 7pm at Vinoy Park in St. Pete! The Florida Orchestra will perform movie music, Broadway hits and & favorites, with family activities starting at 5pm. Enjoy The Dalí Museum’s activity table, a TFO Instrument Petting Zoo, performances by St. Pete Community Band & community sing-along with The Master Chorale of Tampa Bay. Bring non-perishable food donations to support Metropolitan Ministries and enjoy an evening of music.
Learn more at https://floridaorchestra.org/event/free-pops-in-the-park-2/.
#5 FLBG’s Pumpkinfest
Celebrate the season with pumpkin-filled fun at PumpkinFest this Saturday, October 24th 10am–2pm at the Florida Botanical Gardens in Largo! This free family-friendly event features pumpkin carving and painting, fall crafts, a garden-wide scavenger hunt and the chance to plant a seed to take home. Explore the Majeed Discovery Garden, enjoy the fall festivities & make seasonal memories together. Free admission & parking make this a great outing for the whole family!
Learn more at https://flbgfoundation.org/pumpkinfest.