Upcoming Food & Drinks Events

Derby on Park (Kentucky Derby Party)

 Mercedes-Benz of Orlando 2 May 2026
KENTUCKY-DERBY

Cheers to Kindness Gala

 Venue on Lake Lily - Maitland Civic Center 8 May 2026
CHARITIES

Wine and Cheese

 190 Independence Ln, Maitland, FL 32751-5625, United States 7 May 2026
MUSIC

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Upcoming Live Music Events

Maitland Earth Market

 1776 Independence Lane, Maitland, FL, United States, Florida 32751 26 Apr 2026
MUSIC

Jessy J in Maitland

 10 Apr 2026
CONCERTS

Spring Open House 2026

 Art & History Museums of Maitland 8 May 2026
ART FREE

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Upcoming Festivals Events

Maitland Jazz and Blues Festival

 1776 Independence Ln 10 Apr 2026
MUSIC USD 0 TO 162

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

 Downtown Maitland 11 Apr 2026
MUSIC

Central FL Juneteenth Celebration – Talent & Performer Casting Call 2026

 Maitland 20 Jun 2026
ENTERTAINMENT USD 0 TO 18

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Trending Events in Maitland

Smile City Comedy Show & Good Times Bar & Grill

 Good Times Bar & Grill 30 Apr 2026
COMEDY USD 7 TO 17

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

 Downtown Maitland 10 Apr 2026
MUSIC

Hannah Stokes Band at Maitland Jazz & Blues Festival

 1776 Independence Ln, Maitland, FL 32751-5639, United States 11 Apr 2026
MUSIC

12th Annual Kentucky Derby Soirée

 Venue on Lake Lily - Maitland Civic Center 2 May 2026
KENTUCKY-DERBY

Taylor Swift Music Bingo @ Good Times Bar & Grill Maitland

 Good Times Bar & Grill 22 Apr 2026
BINGO

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

 Art & History Museums of Maitland 18 Apr 2026
ART FREE

1st ASL Awareness Night with the Solar Bears!

 Orlando Solar Bears 11 Apr 2026

🌿 Kino MacGregor Ashtanga Yoga Workshop (Live in Maitland FL)

 140 Circle Drive , Maitland, FL, United States, Florida 32751 10 Apr 2026
HEALTH-WELLNESS

FREE Summer Family Art Workshops - Week 2: Nature Wands

 Art & History Museums of Maitland 10 Jun 2026
ART FREE

Rock da Floor Kid's Dance Battle National Championship

 Venue on Lake Lily / Maitland Civic Center 11 Apr 2026
KIDS USD 0 TO 66

FREE Summer Family Art Workshops - Week 1: Friendship Sculptures

 Art & History Museums of Maitland 3 Jun 2026
ART FREE

FREE Summer Family Art Workshops - Week 3: Soft Sculpture Bugs

 Art & History Museums of Maitland 24 Jun 2026
ART FREE

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

 Art & History Museums of Maitland 1 Jul 2026
ART FREE

FREE Summer Family Art Workshops - Week 6: Recycled Bird Sculptures

 Art & History Museums of Maitland 22 Jul 2026
ART FREE

3rd Annual "Blacker The Berry..."

 Venue on Lake Lily / Maitland Civic Center 27 Jun 2026
ART USD 31 TO 42

More things to do in Maitland

Food & Drinks
Live Music
Festivals
Music Festivals
Comedy
St. Patrick's Day
Fireworks
Pop-Ups