Upcoming Live Music Events

Jessy J in Maitland

 10 Apr 2026
CONCERTS

Spring Open House 2026

 Art & History Museums of Maitland 8 May 2026
ART FREE

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

 Good Times Bar & Grill 16 Apr 2026
MUSIC USD 25

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Upcoming Food & Drinks Events

Derby on Park (Kentucky Derby Party)

 Mercedes-Benz of Orlando 2 May 2026
KENTUCKY-DERBY

Young Chefs Academy- Spring Break Culinary Camp

 120 Independence Lane, Suite C, Maitland, FL 16 Mar 2026
FOOD-DRINKS

Cheers to Kindness Gala

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

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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

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

 Art & History Museums of Maitland 18 Apr 2026
ART FREE

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Trending Events in Maitland

St Patrick’s Day Celebration at An Tobar!!

 An Tobar Irish Pub 17 Mar 2026
MUSIC

GOOD FRIDAY Miracle Healing Service with Pastor Billy Burke

 Sheraton Orlando North 3 Apr 2026
GOOD-FRIDAY

🎷🎶 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

Smile City Comedy Show & Good Times Bar & Grill

 Good Times Bar & Grill 19 Mar 2026
COMEDY USD 7 TO 19

Laughing Stock Comedy Night at The Good Times

 Good Times Bar & Grill 26 Mar 2026
COMEDY

Maitland Movies in the Park - Moana 2

 1776 Independence Lane, Maitland, FL, United States, Florida 32751 21 Mar 2026
ENTERTAINMENT

12th Annual Kentucky Derby Soirée

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

Orlando Miracle Service with Pastor Billy Burke

 Sheraton Orlando North 15 Mar 2026
GOOD-FRIDAY

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

GemCon

 641 S Maitland Ave, Maitland, FL 32751, United States 22 Mar 2026
SPORTS

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 6: Recycled Bird Sculptures

 Art & History Museums of Maitland 22 Jul 2026
ART FREE

More things to do in Maitland

Live Music
Food & Drinks
Festivals
Comedy
Music Festivals
Easter
St. Patrick's Day
Black History Month
Easter Egg Hunt