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

Central FL Juneteenth Celebration – Talent & Performer Casting Call 2026

 Sat, 20 Jun at 12:00 pm Maitland USD 0 to 18

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

Hannah Stokes Band at Maitland Jazz & Blues Festival

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

Maitland Earth Market

 Sun, 26 Apr at 08:00 am 1776 Independence Lane, Maitland, FL, United States, Florida 32751

Derby on Park (Kentucky Derby Party)

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

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

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

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

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

Wine and Cheese

 Thu, 07 May at 05:30 pm 190 Independence Ln, Maitland, FL 32751-5625, United States

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

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

Lounge Lyzrds at Good Times - 4/17/26

 Fri, 17 Apr at 08:00 pm Good Times Bar & Grill

Slavic Party

 Sat, 02 May at 07:00 pm 1271 Semoran Blvd USD 32

BEATLES TRIBUTE - TOPPERMOST returns to Good Times Bar & Grill

 Sun, 21 Jun at 04:00 pm Good Times Bar & Grill USD 25 to 42

GODSMACK TRIBUTE - AWAKE

 Sun, 28 Jun at 04:00 pm Good Times Bar & Grill USD 19 to 36