Entertainment events in Maitland

Check out happening entertainment events all around Maitland, FL

🎷🎶 Maitland Jazz & Blues Festival is BACK! 🎶🎷

 Sat, 11 Apr at 02:00 pm Downtown Maitland

🎷🎶 Maitland Jazz & Blues Festival is BACK! 🎶🎷

 Fri, 10 Apr at 06:00 pm Downtown Maitland

Corks and Forks

 Sat, 14 Mar at 07:00 am Venue on Lake Lily / Maitland Civic Center

Getdown Downtown

 Fri, 06 Feb at 06:00 pm 1776 Independence Lane, Maitland, FL, United States, Florida 32751

Oh Snap! A "School's Out" Family Day at A&H

 Mon, 16 Feb at 10:00 am Art & History Museums of Maitland USD 0 to 13

Good Times Bar Valentines Party

 Sat, 14 Feb at 08:00 pm Good Times Bar & Grill

FREE Earth Day Family Day at A&H + Printed Tote Bag Family Art Workshop

 Sat, 18 Apr at 10:00 am Art & History Museums of Maitland Free

Groove Slayers PARTY at Good Times

 Sat, 21 Feb at 09:00 pm Good Times Bar & Grill

FREE Summer Family Art Workshops - Week 4: Printmaking Party!

 Wed, 01 Jul at 10:00 am Art & History Museums of Maitland Free

A&H: The Art Party 2026

 Sat, 07 Mar at 06:00 pm 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Dining in the Dark

 Thu, 19 Feb at 06:00 pm Sheraton Orlando North Hotel

Comedy Night at The Good Times

 Thu, 12 Feb at 07:00 pm Good Times Bar & Grill

Oh Snap! A "School's Out" Family Day at A&H

 Fri, 24 Apr at 10:00 am Art & History Museums of Maitland USD 0 to 13

Smile City Comedy Show & Good Times Bar & Grill

 Thu, 19 Feb at 06:30 pm Good Times Bar & Grill USD 6 to 21

Hannah Stokes Band at Maitland Jazz & Blues Festival

 Sat, 11 Apr at 04:00 pm 1776 Independence Ln, Maitland, FL 32751-5639, United States

GRATEFUL DEAD TRIBUTE - DEAD SET FLORIDA

 Sun, 08 Feb at 04:00 pm Good Times Bar & Grill USD 19 to 31

ALL STAR TRIO - featuring TONY HARNELL - TNT, ANTHONY CORDER - TORA TORA & PJ FARLEY - TRIXTER

Sun, 08 Mar at 06:00 pm Good Times Bar & Grill

Maitland Jazz and Blues Festival

 Fri, 10 Apr at 06:00 pm Independence Ln, Maitland, FL 32751, United States

METALLICA TRIBUTE - MEDAL MILITIA and ALICE IN CHAINS TRIBUTE - THE ROOSTER

 Sun, 15 Mar at 04:00 pm Good Times Bar & Grill USD 13 to 25

Sip & Support

Thu, 26 Mar at 06:30 pm Mercedes-Benz of Orlando

Music in the Gallery (collab. with Howie Music + CFC2)

 Wed, 27 May at 05:30 pm Art & History Museums of Maitland Free

Rock da Floor Kid's Dance Battle National Championship

 Sat, 11 Apr at 12:00 pm Venue on Lake Lily / Maitland Civic Center USD 0 to 66

Maitland Puzzle Exchange

 Sun, 22 Feb at 02:00 pm Maitland Public Library