Leesburg Music Events

Christmas Festival & Parade

500 W Main St, Leesburg, FL 34748, United States 6 Dec 2025

Trick or Treat on Main St.

500 W Main St, Leesburg, FL 34748, United States 25 Oct 2025

Discover Leesburg

500 W Main St, Leesburg, FL 34748, United States 12 Dec 2025

Shamrockin Fest BBQ & Beer Festival - March 13th & 14th - Leesburg, FL

500 W. Main Street, Leesburg, FL, United States, Florida 34748 13 Mar 2026

Cruisin' for St. Jude - Escorted Ride

1745 US Highway 441, Leesburg, FL, United States, Florida 34748 4 Oct 2025

Harry "O" Jazz & Blues at the Speakeasy

118 S 2nd St, Leesburg, FL, United States, Florida 34748 11 Oct 2025

Lupe on Keys at the Speakeasy

118 S 2nd St, Leesburg, FL, United States, Florida 34748 4 Oct 2025

Stevie G's Las Vegas Spectacular

Pennbrooke Fairways 25 Jan 2026

October • WORSHIP ON THE WATER •NEW TIME 5:00pm*

Venetian Gardens, Leesburg 19 Oct 2025

Discover Leesburg

500 W Main St, Leesburg, FL 34748, United States 14 Nov 2025

Discover Leesburg

500 W Main St, Leesburg, FL 34748, United States 10 Oct 2025

PHANTASMAGORIA XVI “Hauntingly Whimsical Tales”

122 W. Main St., Leesburg, FL, United States, Florida 34748 3 Oct 2025

Phantasy Floyd @ The Warehouse Club (An Evening Dedicated To Pink Floyd)

MFPSA – Military, Fire, Police Support Association 15 Nov 2025

Ultimate Santana Tribute @ The Warehouse Social Club & Eatery

MFPSA – Military, Fire, Police Support Association 18 Oct 2025

Classic R&B After Dark 4th Street

100 S 4th ST, Leesburg, FL 18 Oct 2025

Son☀Rae RED🎖SHIRT FRIDAY🎤KARAOKE at FRANK'S🎱PLACE in LEESBURG f/ 9PM-1AM w/ DJ🎙JEFF-fa-fa!

Frank's Place 3 Oct 2025

Gator Bike Rally | Fall 2025

1745 US HWY 441, Leesburg, FL, United States, Florida 34748 14 Nov 2025

Thursday Karaoke w/ DJ RUSSMAN

The Warehouse Club - Military Fire Police Support Association 2 Oct 2025

Tuesday Night Karaoke & Taco Tuesday - Corona Specials & More

312 S. 2nd Street, Leesburg, FL 30 Sep 2025

Sandy Back Porch @ Leesburg Library

100 E Main St, Leesburg, FL 34748 3 Oct 2025

Leesburg Blues Brothers

Pennbrooke Fairways 15 Feb 2026

Atlantic City Boys

Pennbrooke Fairways 15 Mar 2026

U2 Ultimate Tribute @ The Warehouse (U2-2U)

The Warehouse Social Club operated by the Military Fire Police Support Association 17 Jan 2026

Second Thursday BIKE NIGHTS, Downtown Leesburg FL @ 5pm. HAPPY HOUR starts @ 4pm!

311 W. Magnolia, Leesburg, FL, United States, Florida 34748 9 Oct 2025

Shades of Rock at Gator Bay 🌞

Gator Bay Bar & Grill 26 Oct 2025

Son☀Rae🎤KARAOKE at THE🎶WAREHOUSE in LEESBURG EVERY 2nd & 4th TUESDAY f/ 6-10PM w/🎙DJ JEFF-fa-fa!

The Warehouse Social Club & Eatery - Live Music, Karaoke, Arcade & More 14 Oct 2025

Toppermost Beatles @ The Warehouse - Leesburg (Ultimate Beatles Tribute)

MFPSA – Military, Fire, Police Support Association 20 Dec 2025

Son☀Rae🎤KARAOKE🐪WEDNESDAYS at The BRICK & BARREL in LEESBURG f/ 6-9PM w/ DJ🎙JEFF-fa-fa & SHELBY!

The Brick & Barrel Public House Leesburg, FL 1 Oct 2025

RRCC's 5th Year Anniversary Weekend Celebration

Lake Yale Baptist Conference Center 9 Jan 2026

DuPLEXer returns to rock GATOR BAY

Gator Bay Bar & Grill 27 Dec 2025

Veterans Day Parade

500 W Main St, Leesburg, FL 34748, United States 8 Nov 2025

Time Machine at Gator Harley Davidson - Toy Run

GATOR HARLEY-DAVIDSON 6 Dec 2025

Benefit Concert @ The Warehouse Social Club

The Warehouse Club - Military Fire Police Support Association 26 Oct 2025