Upcoming Maitland Events

Check out what's happening all around Maitland, FL

Maitland Jazz and Blues Festival

 Fri, 10 Apr at 06:00 pm 1776 Independence Ln USD 0 to 162

🎷🎶 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

12th Annual Kentucky Derby Soirée

 Sat, 02 May at 06:00 pm Venue on Lake Lily - Maitland Civic Center

Taylor Swift Music Bingo @ Good Times Bar & Grill Maitland

 Wed, 22 Apr at 07:00 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

1st ASL Awareness Night with the Solar Bears!

 Sat, 11 Apr at 07:00 pm Orlando Solar Bears

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

 Fri, 10 Apr at 05:00 pm 140 Circle Drive , Maitland, FL, United States, Florida 32751

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

FREE Summer Family Art Workshops - Week 2: Nature Wands

 Wed, 10 Jun at 10:00 am 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

Jessy J in Maitland

 Fri, 10 Apr at 08:00 pm

Spring Open House 2026

 Fri, 08 May at 06:30 pm Art & History Museums of Maitland Free

FREE Summer Family Art Workshops - Week 1: Friendship Sculptures

 Wed, 03 Jun at 10:00 am Art & History Museums of Maitland Free

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

 Wed, 24 Jun at 10:00 am Art & History Museums of Maitland Free

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

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

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

 Wed, 22 Jul at 10:00 am Art & History Museums of Maitland Free

3rd Annual "Blacker The Berry..."

 Sat, 27 Jun at 05:00 pm Venue on Lake Lily / Maitland Civic Center USD 31 to 42

FREE Summer Family Art Workshops - Week 5: Mini Yarn Tapestries

 Wed, 08 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

Cheers to Kindness Gala

 Fri, 08 May at 06:00 pm Venue on Lake Lily - Maitland Civic Center

Pampered & Empowered ~ Women's Retreat

 Sun, 19 Apr at 05:00 pm Venue on Lake Lily / Maitland Civic Center USD 31

Taylor Swift Music Bingo @ Selva Rosa Maitland

 Wed, 15 Apr at 07:00 pm Selva Rosa

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

14th Annual Diversity Awards

Fri, 29 May at 12:30 pm Sheraton Orlando North Hotel

Smile City Comedy Show & Good Times Bar & Grill

 Thu, 30 Apr at 06:30 pm Good Times Bar & Grill USD 7 to 17

Vendor and Sponsorship Opportunities ~ JOIN US IN EMPOWERING WOMEN

 Sun, 19 Apr at 03:30 pm Venue on Lake Lily / Maitland Civic Center USD 25 to 379

Island Vibes Music Bingo @ Good Times Bar & Grill Maitland

 Wed, 15 Apr at 07:00 pm Good Times Bar & Grill

Wine and Cheese

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

Ultimate Santana Tribute at Good Times Bar & Grill in Maitland, FL

 Sun, 24 May at 07:00 pm Good Times Bar & Grill USD 22 to 30

Realtors: GET FOUND IN AI SEARCH

 Tue, 21 Apr at 10:00 am 2301 Maitland Center Pkwy suite 180 Free

Homeschool Day at the Telephone Museum

 Fri, 01 May at 10:00 am Art & History Museums of Maitland USD 7 to 13

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

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

Engineered for Growth: AI, Social & Production 2026

 Thu, 30 Apr at 05:00 pm 810 N Orlando Ave Free

Stephanie Phillips Signing

 Sat, 18 Apr at 02:00 pm 500 E Horatio Avenue, Maitland, FL

SPEED LIMIT 70 Debut at Good Times, 5/2/26

 Sat, 02 May at 08:00 pm Good Times Bar & Grill

ADHD 2.0 Training: Transforming ADHD with Advanced Diagnostic Techniques

 Sat, 09 May at 09:30 am Maitland Wellness Center USD 229 to 259

CLEARWATER A Tribute to CCR

 Sun, 03 May at 06:00 pm Good Times Bar & Grill USD 25

Lounge Lyzrds at Good Times - 4/17/26

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

Maitland Library‑Hosted Board Game Day

 Sat, 18 Apr at 10:30 am Maitland Public Library

✨ Flow & Sound: A 75-Minute Vinyasa + Sound Bath with Marilyn Glasser & Laura Daniel | April 12

 Sun, 12 Apr at 10:30 am 140 Circle Drive , Maitland, FL, United States, Florida 32751

Maitland Area Chamber Speed Networking Event

 Tue, 14 Apr at 05:30 pm Art & History Museums of Maitland USD 34

Art Workshop: Pet Portraits

 Sat, 25 Apr at 09:30 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

200 Hour Yoga Teacher Training – 2026 Ashtanga Apprenticeship with Krista

 Fri, 16 Jan at 07:30 am 140 Circle Dr Free

Art Workshop: Inner Terrain: Abstract Landscape

 Sat, 09 May at 09:30 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Yoga on the Lawn - Open Community Event

 Sat, 02 May at 08:30 am 1450 S Orlando Ave, Maitland, FL, United States, Florida 32751

Luncheon and Fashion Show Fundraiser

 Sat, 25 Apr at 10:00 am Venue on Lake Lily - Maitland Civic Center

Hearts & Crafts for Women: "A New Creation"

 Sat, 11 Apr at 03:00 pm 501 Maitland Ave S Free

Studio Nights: Nights of Worship

 Sat, 11 Apr at 07:00 pm 901 N Lake Destiny Rd Free

Free Curator Tour

 Wed, 29 Apr at 06:00 pm Art & History Museums of Maitland Free

Sound Bath in the Park

 Sat, 02 May at 09:30 am Lake Lily Park Free

Slavic Party

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

Obsessive-Compulsive Disorder 101: Evidence-Based Assessment and Treatment

 Wed, 29 Apr at 05:30 pm Venue on Lake Lily / Maitland Civic Center USD 15 to 25

Art Workshop: Sweet Strokes: Painting Desserts in Impasto

 Sat, 23 May at 09:30 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

A&H Book Club: May 2026 Meeting

 Sun, 17 May at 03:00 pm Maitland Art Center gallery USD 7

Home Inspection Strategy 3h CE

 Wed, 20 May at 10:00 am EXIT Global Realty Free

Real Producers Playbook: Ask the Expert Agents

 Thu, 21 May at 09:30 am Venue on Lake Lily / Maitland Civic Center USD 0 to 13

Maitland Farmers Market

Sun, 12 Apr Maitland Farmers Market

REALTORS: Track Your Way to the Top!

 Wed, 22 Apr at 11:30 am EXIT Global Realty

General Trivia at Brewlando Maitland

 Thu, 02 Apr Brewlando Maitland

AltEra Debut at Good Times Bar and Grill!

 Sat, 09 May at 08:00 pm Good Times Bar & Grill

BEATLES TRIBUTE - TOPPERMOST returns to Good Times Bar & Grill

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

Art Workshop: Watercolor Journal Workshop

 Thu, 28 May at 06:30 pm 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Global Rhythm

 Sat, 04 Apr at 02:00 pm Art & History Museums of Maitland USD 135

Car Seat Safety Check & Installation

 Sat, 02 May at 09:00 am Lake Lily Park Free

Exclusive Dating Event | Flame Elite | Orlando

 Sat, 09 May at 10:00 am 1271 Semoran Blvd USD 50 to 535

Homeschool Tween/Teen MAITLAND CREATIVE CHALLENGE

 Fri, 24 Apr at 11:00 am Lake Sybelia Beach Park Free

Yom HaShoah Commemoration

 Sun, 19 Apr at 03:00 pm 851 N Maitland Ave Free

Fall Fest 2026!

 Sat, 26 Sep at 07:00 am 600 N Lake Destiny Rd USD 25 to 71

REALTOR Lunch & Learn: Track Your Way to the Top

 Wed, 22 Apr at 11:30 am EXIT Global Realty Free

Free Curator Tour

 Wed, 29 Jul at 06:00 pm Art & History Museums of Maitland Free

Taste of Midwifery: A Birth and Baby Expo Volunteer

 Sat, 02 May at 08:00 am Lake Lily Park Free

Benefit for Bill

 Sun, 26 Apr at 11:00 am 1720 Fennell St, Maitland, FL 32751-8672, United States

Faithless Under 40

 Tue, 14 Apr at 11:00 am Lazy Moon Pizza Maitland

"Mezuzah Traces: Memory on the Doorposts of Poland"

 Thu, 06 Aug at 05:00 pm 851 N Maitland Ave Free

GODSMACK TRIBUTE - AWAKE

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

Exhibition - a loom, a fence, a wire, a thread

 Sat, 25 Apr at 11:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Housing and Transportation Cohort Training

 Sat, 18 Apr at 11:00 am Eatonville Library - 200 E Kennedy Blvd, Eatonville 32751

Lefkada Yoga Retreat 2026 with Krista Shirley: Ashtanga, Movement & Culture

 Fri, 10 Jul at 06:00 am The Yoga Shala USD 500 to 3,436

A&H Book Club: September 2026 Meeting

 Sun, 20 Sep at 03:00 pm Maitland Art Center gallery USD 7

Dining Out Group - 4/29/26 Dinner Parea Greek Taverna Maitland 5:30pm

 Wed, 29 Apr at 05:30 pm Parea Greek Taverna

Team Florida Meet & Greet and Flag Signing

 Sat, 16 May at 01:00 pm 900 Winderley Pl, Maitland, FL 32751-4191, United States

Art Workshop: Kitchen Lithography Printing

 Sat, 06 Jun at 11:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Fragility of Democracy Session 2 - "Myths, Money, and the Making of Blame"

 Sun, 12 Apr at 12:00 pm 851 N Maitland Ave Free

Fragility of Democracy Session 4 - "When Law Becomes Weapon"

 Sun, 02 Aug at 12:00 pm 851 N Maitland Ave Free

Fragility of Democracy Session 5 - "Words That Wound"

 Sun, 04 Oct at 12:00 pm 851 N Maitland Ave Free

A&H Book Club: July 2026 Meeting

 Sun, 19 Jul at 03:00 pm Maitland Art Center gallery USD 7

Spelling Bee

 Fri, 08 May at 06:00 pm 500 E Horatio Avenue, Maitland, FL

Little Creatives

 Wed, 15 Apr at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Maitland Meet and Greet

Tue, 21 Apr at 06:00 pm 441 S Orlando Ave, Maitland, FL 32751

Fragility of Democracy Session 3 - "Culture Under Fire"

 Sun, 31 May at 12:00 pm 851 N Maitland Ave Free

Art Workshop: Automatic Drawing

 Sat, 02 May at 11:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Little Creatives & Me

 Wed, 20 May at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Little Creatives & Me at A&H

 Wed, 19 Oct at 10:00 am Art & History Museums of Maitland Free

General Meeting/Installation of Officers/Luncheon

 Sat, 16 May at 11:30 am Venue on Lake Lily - Maitland Civic Center

Maitland, FL: M**der Mystery Detective Experience

 Mon, 28 Nov at 10:00 am Maitland & Area (Orlando North) CAD 20

Kindergarten Popsicles in the Park

 Sat, 08 Aug at 10:00 am Dommerich Elementary