September Events & Latest Happenings:

September 5 - First Fridays at Friendship Fountain | First Fridays at the Fountain happen the first Friday of the month from 5-9:30 p.m. The special event will have a DJ, cash bar, food trucks, vendors, and lawn games all localized at the Fountain! Click here for more information.

• September 5 - Adam Sandler | VyStar Veterans Memorial Area. Comedy legend Adam Sandler brings his You’re My Best Friend Tour to VyStar Veterans Memorial Arena on Friday, September 5, 2025, for a night of laughter, music, and nostalgia. Don’t miss the kickoff of his 33-city tour, filled with his signature humor and fan-favorite moments. Click here to snag your tickets.

• September 6 - Historic Avondale Pairing Walking Tour | Experience a progressive tasting tour through four top spots in the historic Shoppes of Avondale, featuring chef-driven bites, perfectly paired wines or cocktails, and unforgettable hospitality. Enjoy a guided stroll through one of Jacksonville’s most charming neighborhoods as you savor bold flavors and local history. Learn more here.

• September 10 - Live Jazz & Wine Down Wednesday | Featuring local Jazz and soul artists!

  Join us for smooth grooves, soulful melodies & cozy ambiance. Perfect pairing with dinner and drinks — swing by to experience a moody evening of wine and Jazz! Click here to get your tickets.

• September 13 - USS Orleck 80th Birthday Bash | Celebrate the legendary Gearing‑class destroyer’s milestone aboard the USS Orleck at the Jacksonville Naval Museum—with food trucks, a car show, live DJ music courtesy of DJ RandMX, amateur-radio broadcasts from WJ4DD, and ship tours for a special price of just $8.86. Check out the details here.

• September 20 - Yoga at Riverview Park | Certified instructor Tahirah Hamilton leads free “Yoga at the Park” every 3rd Saturday at 9 AM in Riverview Park. Bring your mat, enjoy the oak trees and Trout River views, and start your weekend with a relaxing class—beginners welcome! Learn more here. 

• September 27 - 7th Annual Oktoberfest at Legacy Ale Works | Legacy Ale Works has a packed season ahead with Oktoberfest on Sept 27, the Homebrew Festival on Oct 18, Dueling Pianos on Oct 24, and the Fall Fest & Market on Nov 16. From beer games and live music to local makers and special pairings, there’s something for everyone to enjoy. Click here for details.