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

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

Derby on Park (Kentucky Derby Party)

 Sat, 02 May at 04:30 pm Mercedes-Benz of Orlando

Jessy J in Maitland

 Fri, 10 Apr at 08:00 pm

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

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

Lounge Lyzrds at Good Times - 3/13/26

 Fri, 13 Mar at 08:00 pm Good Times Bar & Grill

Nathan Mitchell at Jazz Tastings

 Sat, 14 Mar at 07:00 pm 164 Lake Ave, Maitland, FL, United States, Florida 32751

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 Mar at 06:30 pm Good Times Bar & Grill USD 7 to 19

A&H: The Art Party 2026

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

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

Rico Monaco Band LIVE — One Night Only at Good Times Bar & Grill

 Thu, 16 Apr at 07:00 pm Good Times Bar & Grill USD 25

GRATEFUL DEAD TRIBUTE - DEAD SET FLORIDA

 Sun, 29 Mar at 04:00 pm Good Times Bar & Grill USD 19 to 31

Discover Your Wellness

 Thu, 05 Mar at 05:00 pm 260 Lookout Place, Suite 107, Maitland, FL, United States, Florida 32751

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

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

Sip & Support

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

Hannah Stokes Band at Maitland Jazz & Blues Festival

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

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

ORIGINAL MUSIC ARTIST SHOWCASE with CLEM ROCKZ and others GOOD TIMES

 Sun, 22 Mar at 03:30 pm Good Times Bar & Grill USD 19

General Trivia at Brewlando Maitland

 Thu, 26 Mar at 07:00 pm Brewlando Maitland

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

Mommy and Me Tea Time | Weekend Mornings at Healing Mama Studio

 Sun, 07 Sep at 10:00 am Healing Mama Studio USD 19 to 69