Upcoming Maitland Events

Check out what's happening all around Maitland, FL

Jazz Tastings Halloween Party!

 Fri, 31 Oct at 06:00 pm 164 Lake Ave, Maitland, FL, United States, Florida 32751

1887 First Weekend

Sat, 01 Nov at 02:00 pm 307 E Kennedy Blvd, Maitland, FL 32751-6800, United States

Free Winter Family Day at A&H + Wintery Family Art Workshop

 Sat, 06 Dec at 10:00 am Art & History Museums of Maitland Free

Eden Bar Halloween Party

 Fri, 31 Oct at 08:00 pm 1300 S Orlando Ave, Maitland, FL, United States, Florida 32751

Appreciation Winter Wonderland Gala 2025

 Fri, 12 Dec at 06:00 pm Venue on Lake Lily - Maitland Civic Center

Maitland's Getdown Downtown

 Fri, 07 Nov at 06:00 pm 1776 Independence Ln, Maitland, FL 32751-5639, United States

Financial Literacy Bootcamp

 Sat, 15 Nov at 11:00 am WSB Maitland Financial Education Center Free

Heirs' Property & Estate Planning Education Session

 Sat, 08 Nov at 10:30 am Christ Centered Church & Ministries Free

Equality Florida's 2025 Greater Orlando Gala

 Sat, 01 Nov at 06:00 pm Sheraton Orlando North Hotel

Celebration of Filipino Culture

 Wed, 19 Nov at 05:30 pm Art & History Museums of Maitland Free

Bookbinding: Japanese Stitching

 Sat, 08 Nov at 11:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Orlando Greek Fest

 Fri, 07 Nov at 11:00 am Holy Trinity Greek Orthodox Church of Greater Orlando Free

Winter Youth Music Festival, 2nd Annual

 Sun, 09 Nov at 12:00 pm Good Times Bar & Grill Free

The Polyvagal Theory and Powerful Calming Techniques

 Sat, 15 Nov at 09:30 am Imperial Counseling and Coaching LLC USD 215 to 242

Orlando Greek Fest 2025

 Fri, 07 Nov at 04:00 pm 1217 Trinity Woods Ln, Maitland, FL, United States, Florida 32751

Junior Reading Club: “I Will Come Back For You”

 Sun, 23 Nov at 12:00 pm 851 N Maitland Ave Free

Ultimate Rush Tribute at Good Times Bar & Grill

 Sun, 30 Nov at 05:00 pm Good Times Bar & Grill USD 13 to 31

Pampered & Empowered

 Sun, 07 Dec at 05:00 pm Venue on Lake Lily / Maitland Civic Center USD 45

BCO Presents: Echoes of Nordic and Romantic Spirits

 Sun, 16 Nov at 04:00 pm Maitland Presbyterian Church USD 23

Women in Tech & Entrepreneurship - Orlando Holiday Party

 Tue, 18 Nov at 05:30 pm Enzian Theater Free

Good Times Bar Dance Party

 Fri, 07 Nov at 08:00 pm Good Times Bar & Grill

We Appreciate You Day!

 Sat, 01 Nov at 11:00 am Maitland Community Park Free

BEE GEES TRIBUTE - JIVE TALKIN

 Thu, 13 Nov at 07:00 pm Good Times Bar & Grill USD 31 to 36

The Players TRIO - Live at Good Times Bar & Grill

 Sun, 09 Nov at 07:00 pm Good Times Bar & Grill

Junior Reading Club: “Hanukkah Bear”

 Sun, 14 Dec at 12:00 pm 851 N Maitland Ave Free

Masquerade Gala

 Fri, 14 Nov at 07:00 pm 1236 E Lake Colony Dr USD 185

2 Part Halloween Party at Good Times Bar & Grill!!

 Fri, 31 Oct at 07:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Drawing a Surrealist Dreamscape

 Tue, 11 Nov at 06:00 pm 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Ultimate Floyd Tribute at Good Times Bar & Grill

 Sat, 29 Nov at 08:00 pm Good Times Bar & Grill USD 13 to 31

Maitland Downtown Get Down Street Party

 Fri, 07 Nov at 06:00 pm 1776 Independence Ln, Maitland, FL 32751-5639, United States

A&H Book Club: November 2025 Meeting

 Sun, 16 Nov at 03:00 pm Maitland Art Center gallery USD 7

Maitland Move in the Park

 Sat, 15 Nov at 06:00 pm 1776 Independence Ln, Maitland, FL 32751-5639, United States

Lumière presents: AFROHOUSE AND COFFEE!

 Sat, 01 Nov at 10:00 am Lumiere Cosmetic and Implant Dentistry USD 23

Creating a Pop Art Portrait

 Tue, 18 Nov at 06:00 pm 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Winter Studio Show 2025

 Fri, 12 Dec at 06:30 pm Art & History Museums of Maitland Free

November Volunteer Day

 Thu, 06 Nov at 10:00 am 900 Winderley Place, Suite 2200, Maitland, FL, United States, Florida 32751

Orlando Miracle Service with Pastor Billy Burke

 Sun, 16 Nov at 07:00 pm Sheraton Orlando North

Midnight Mayhem Takes Over Good Times Bar & Grill November 1st!

 Sat, 01 Nov at 08:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Kristallnacht Commemoration Event

 Sun, 09 Nov at 03:00 pm 851 N Maitland Ave Free

Lounge Lyzrds at Good Times - 12/5/25

 Fri, 05 Dec at 08:00 pm Good Times Bar & Grill

Art Journaling

 Sun, 07 Dec at 11:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Running With Scissors returns to Good Times Bar & Grill November 8th!

 Sat, 08 Nov at 08:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Maitland Farmers Market

Sun, 07 Dec at 09:00 am Maitland Farmers Market

General Trivia at Brewlando Maitland

 Thu, 06 Nov at 07:00 pm Brewlando Maitland

A Taste of Marbling on Paper and Glass Baubles

 Wed, 12 Nov at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

MMS WINTER DANCE!

 Fri, 05 Dec at 07:00 pm 701 N. Thistle Lane, Maitland, FL

Shelia & The Sound return to Good Times Bar & Grill November 7th

 Fri, 07 Nov at 07:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Veteran's Salute

 Sun, 09 Nov at 04:00 pm 641 Maitland Ave S USD 0 to 5

Fire Rhythms returns to Good Times Bar & Grill November 15th!

 Sat, 15 Nov at 08:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Maitland Farmers Market

Sun, 14 Dec at 09:00 am Maitland Farmers Market

Faithless Under 40

 Sun, 09 Nov at 11:00 am Maitland Social

General Trivia at Brewlando Maitland

 Thu, 13 Nov at 07:00 pm Brewlando Maitland

Halloween Abyss with DJ Lavidicus at Good Times Bar & Grill October 31st!

 Fri, 31 Oct at 10:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Abyss HALLOWEEN 🎃

Fri, 31 Oct at 10:00 pm Good Times Bar & Grill

Maitland Farmers Market

Sun, 21 Dec at 09:00 am Maitland Farmers Market

Homeschool Day at A&H: Architecture Tour & Printmaking Workshop

 Fri, 14 Nov at 10:00 am Art & History Museums of Maitland USD 7 to 13

Doc Fu & The Soul Surgeons return to Good Times Bar & Grill November 22nd!

 Sat, 22 Nov at 08:00 pm 1720 Fennell St,, Maitland, FL, United States, Florida 32751

Cyanotype Printing

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

General Trivia at Brewlando Maitland

 Thu, 20 Nov at 07:00 pm Brewlando Maitland

Maitland Farmers Market

Sun, 09 Nov at 09:00 am Maitland Farmers Market

General Trivia at Brewlando Maitland

 Thu, 04 Dec at 07:00 pm Brewlando Maitland

Ashtanga Yoga Workshop | November 16th

 Sun, 16 Nov at 08:00 am The Yoga Shala USD 25 to 85

Maitland Farmers Market

Sun, 16 Nov at 09:00 am Maitland Farmers Market

Why NEW Construction needs a HOME INSPECTION too!

 Wed, 19 Nov at 11:00 am EXIT Global Realty Free

Just Priest returns to Good Times Bar & Grill with special guests Kings County

 Thu, 20 Nov at 07:00 pm Good Times Bar & Grill

Agency Apéritif: Connect w/Ad & Film Professionals @ The Enzian Eden Bar

 Wed, 19 Nov at 06:00 pm Eden Bar USD 0 to 13

Maitland Farmers Market

Sun, 23 Nov at 09:00 am Maitland Farmers Market

General Trivia at Brewlando Maitland

 Thu, 18 Dec at 07:00 pm Brewlando Maitland

Virtual Dementia Tour Experience

 Thu, 06 Nov at 09:00 am 1551 Sandspur Rd. , Maitland, FL, United States, Florida 32751

Behind the Blend with Stephen Wilson - Orlando

 Tue, 18 Nov at 02:00 pm Packwoods Free

Lake Lily Park Cleanup

 Sat, 01 Nov at 09:30 am 701 Lake Lily Dr, Maitland, FL 32751, United States

Medal Militia returns to Good Times Bar & Grill

 Sun, 14 Dec at 04:00 pm Good Times Bar & Grill

Park Maitland School North Campus - Winter Open House

 Sat, 10 Jan at 09:00 am 1450 S Orlando Ave, Maitland, FL, United States, Florida 32751

Volley On Collegiate Showcase and Camp

 Sat, 22 Nov at 03:00 pm Maitland Center, Maitland, Florida

Landsharks Concert: Maitland, FL

 Fri, 05 Dec at 06:00 pm Maitland Center, Maitland, Florida

Vendor and Sponsorship Opportunities ~ JOIN US IN EMPOWERING WOMEN

 Sun, 07 Dec at 05:00 pm Venue on Lake Lily / Maitland Civic Center USD 150 to 750

Casual Gaming at the Maitland Library

 Sat, 22 Nov at 10:00 am Maitland Public Library

Homeschool Day at the Waterhouse Residence and Carpentry Shop Museums

 Fri, 09 Jan at 10:00 am Waterhouse Residence Museum USD 7 to 13

General Trivia at Brewlando Maitland

 Thu, 11 Dec at 07:00 pm Brewlando Maitland

In Her Name: A Decade of Difference Gala

 Fri, 23 Jan at 06:00 pm 1217 Trinity Woods Ln USD 71 to 10,673

UDD 2nd Annual Ultimate Sweethearts

 Sat, 07 Feb at 10:00 am Sheraton Orlando North Hotel

Homeschool Day at A&H: Architecture Tour & Outdoor Sketching in the Garden

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

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

FREE Early Spring Family Day at A&H + Nature Pinch Pot Family Art Workshop

 Sat, 07 Feb at 10:00 am Art & History Museums of Maitland Free

BUTTERFLY GARDENING

Thu, 13 Nov at 12:00 pm Maidand Community Park 1400 Mayo Ave.

METALLICA TRIBUTE - MEDAL MILITIA and ALICE IN CHAINS TRIBUTE - THE ROOSTER

 Sun, 14 Dec at 04:00 pm Good Times Bar & Grill USD 13 to 25

Luncheon and Fashion Show Fundraiser

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

Corks and Forks

 Sat, 14 Mar at 07:00 am Venue on Lake Lily / Maitland Civic Center

General Meeting: Ctrl+Alt+Defend: Reset your Cyber Habits

 Thu, 05 Mar at 07:00 pm Venue on the Lake - Maitland Civic Center

December Volunteer Day

 Thu, 04 Dec at 10:00 am 900 Winderley Place, Suite 2200, Maitland, FL, United States, Florida 32751

Eatonville 1887 Night Market w/ The Conch Dynasty

 Sat, 01 Nov at 02:00 pm Town of Eatonville Florida

Little Creatives & Me

 Wed, 17 Dec at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

[MasterclassCFL3.0] MO-Vember Session

 Thu, 20 Nov at 09:30 am Venue on Lake Lily / Maitland Civic Center USD 0 to 13

Little Creatives & Me

 Wed, 19 Nov at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Tables Extraordinaire 2026

 Wed, 04 Feb at 10:00 am 1217 Trinity Woods Lane, Maitland, FL, United States, Florida 32751

2025 Joe R. Lee Branch Faces of the Future Breakfast

Thu, 06 Nov at 07:15 am Joe R. Lee Boys & Girls Club

Silk Painted Scarves Galore

 Tue, 11 Nov at 10:00 am 231 W. Packwood Ave, Maitland, FL, United States, Florida 32751

Winter Magical Mahj

 Sun, 07 Dec at 11:30 am Congregation Ohev Shalom

ROLLING STONES TRIBUTE - MUSIC CITY STONES & BITTENBENDER

 Sun, 19 Oct at 04:00 pm Good Times Bar & Grill USD 25

BEAUTY BAR WORKSHOP | THINGS TO DO ON THE WEEKEND AT HEALING MAMA STUDIO

 Sat, 03 May at 06:00 pm 601 N Orlando Ave USD 58 to 115