Best events in
Maitland

For events and things to do in Maitland, FL, the local calendar thrives on lakeside gatherings and creative spaces. The Lake Lily Core anchors outdoor daytime markets and leisurely strolls along the water. Meanwhile, the U.S. 17-92 Commercial Corridor brings together casual dining spots and neighborhood social hubs.

Navigating the Lake Lily Core reveals scenic walking paths that connect directly to the Maitland Farmers Market.
Enzian Theater offers historic single-screen independent cinema paired with open-air drinks at Eden Bar.
The Maitland Social provides a compact community food hall setting with wood-fired pizza and shared indoor-outdoor seating.

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Popular in Maitland

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Free Showcase: The Art of Tango

Tuesday • 6:30 PM

Venue on Lake Lily / Maitland Civic Center

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In Good Company with Skin Pharm Winter Park

Sat, Oct 17 • 9:00 AM

HILI FITNESS

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Little Creatives & Me at A&H

Wed, Oct 21 • 10:00 AM

Art & History Museums of Maitland

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Pink, Powerful & Prepared: Women’s Financial & Health Wellness Night

Thu, Oct 22 • 6:00 PM

495 N Keller Rd

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Thrill The World Orlando 2026

Sat, Oct 24 • 4:30 PM

Genesis Health Clubs – Orlando Sportsplex

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Maitland Falloween

Sat, Oct 24 • 5:30 PM

1776 Independence Ln

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Fragility of Democracy Session 6 - "Judgment and Justice"

Sun, Oct 25 • 12:00 PM

851 N Maitland Ave

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The Business Owner's Playbook

Thu, Nov 5 • 6:00 PM

495 N Keller Rd

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Free Showcase: The Art of Tango

Tuesday • 6:30 PM

Venue on Lake Lily / Maitland Civic Center

Check ticket price on event

In Good Company with Skin Pharm Winter Park

Sat, Oct 17 • 9:00 AM

HILI FITNESS

Check ticket price on event

Little Creatives & Me at A&H

Wed, Oct 21 • 10:00 AM

Art & History Museums of Maitland

Check ticket price on event

Pink, Powerful & Prepared: Women’s Financial & Health Wellness Night

Thu, Oct 22 • 6:00 PM

495 N Keller Rd

Check ticket price on event

Thrill The World Orlando 2026

Sat, Oct 24 • 4:30 PM

Genesis Health Clubs – Orlando Sportsplex

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Maitland Falloween

Sat, Oct 24 • 5:30 PM

1776 Independence Ln

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Fragility of Democracy Session 6 - "Judgment and Justice"

Sun, Oct 25 • 12:00 PM

851 N Maitland Ave

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The Business Owner's Playbook

Thu, Nov 5 • 6:00 PM

495 N Keller Rd

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Online Events

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Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

Check ticket price on event

Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Business & Professional events

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Pink, Powerful & Prepared: Women’s Financial & Health Wellness Night

Thu, Oct 22 • 6:00 PM

495 N Keller Rd

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Tech and Business Networking | Elevating Your Potential - Orlando

Wed, Nov 4 • 6:00 PM

Selva Rosa Cocina & Bar

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The Business Owner's Playbook

Thu, Nov 5 • 6:00 PM

495 N Keller Rd

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REALTOR Lunch & Learn: The True Power of the Purchase Reverse Mortgage

Wed, Nov 18 • 11:30 AM

EXIT Global Realty

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Pink, Powerful & Prepared: Women’s Financial & Health Wellness Night

Thu, Oct 22 • 6:00 PM

495 N Keller Rd

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Tech and Business Networking | Elevating Your Potential - Orlando

Wed, Nov 4 • 6:00 PM

Selva Rosa Cocina & Bar

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The Business Owner's Playbook

Thu, Nov 5 • 6:00 PM

495 N Keller Rd

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REALTOR Lunch & Learn: The True Power of the Purchase Reverse Mortgage

Wed, Nov 18 • 11:30 AM

EXIT Global Realty

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Performing & Visual Arts events

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Free Showcase: The Art of Tango

Tuesday • 6:30 PM

Venue on Lake Lily / Maitland Civic Center

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Interlude: Live Music Activation | VI FIAE

Wednesday • 7:00 PM

Germaine Marvel Building

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Opening Reception: Vilomah

Friday • 6:30 PM

Art & History Museums of Maitland

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Orlando Collage Club Presents: Orlando Photographer, Danielle Darden

Fri, Oct 23 • 6:00 PM

Blackbird Comics & Coffeehouse

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Thrill The World Orlando 2026

Sat, Oct 24 • 4:30 PM

Genesis Health Clubs – Orlando Sportsplex

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Smile City Comedy Show & Good Times Bar & Grill

Thu, Nov 5 • 7:30 PM

Good Times Bar & Grill

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The Start Of Something Big

Mon, Nov 9 • 1:00 PM

Venue on Lake Lily / Maitland Civic Center

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Fall Open House 2026

Fri, Nov 13 • 6:30 PM

Art & History Museums of Maitland

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Free Showcase: The Art of Tango

Tuesday • 6:30 PM

Venue on Lake Lily / Maitland Civic Center

Check ticket price on event

Interlude: Live Music Activation | VI FIAE

Wednesday • 7:00 PM

Germaine Marvel Building

Check ticket price on event

Opening Reception: Vilomah

Friday • 6:30 PM

Art & History Museums of Maitland

Check ticket price on event

Orlando Collage Club Presents: Orlando Photographer, Danielle Darden

Fri, Oct 23 • 6:00 PM

Blackbird Comics & Coffeehouse

Check ticket price on event

Thrill The World Orlando 2026

Sat, Oct 24 • 4:30 PM

Genesis Health Clubs – Orlando Sportsplex

Check ticket price on event

Smile City Comedy Show & Good Times Bar & Grill

Thu, Nov 5 • 7:30 PM

Good Times Bar & Grill

Check ticket price on event

The Start Of Something Big

Mon, Nov 9 • 1:00 PM

Venue on Lake Lily / Maitland Civic Center

Check ticket price on event

Fall Open House 2026

Fri, Nov 13 • 6:30 PM

Art & History Museums of Maitland

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Frequently asked questions about Maitland

What family-friendly events happen around the local parks?

The Maitland Farmers Market provides lively outdoor gatherings featuring lawn games and family activities. Visitors enjoy browsing local produce, exploring craft vendors, and listening to live music situated near the scenic waterfront of Lake Lily Park during weekly community hours.

Where are the best spots for art events and cultural workshops?

The Art & History Museums Maitland serves as a premier venue for local art events and creative community gatherings. This historic site showcases Mayan Revival architecture, hosting educational workshops, guided museum tours, and seasonal art showcases throughout the calendar year.

How can visitors find outdoor movie screenings in the area?

Seasonal park programming brings open-air cinema experiences to local green spaces across the district. The city regularly hosts recurring community movie nights, offering relaxing outdoor entertainment set against neighborhood parks, family lawns, and lively community plazas for all residents.

What are good choices for date night events featuring food and drinks?

The U.S. 17-92 Commercial Corridor offers an array of intimate bistros and craft drink spots. Couples often pair a neighborhood dinner with independent film screenings at the historic Enzian Theater and drinks at the adjacent Eden Bar.

Are there walkable neighborhoods known for food and drink events?

The Lake Lily Core functions as the walkable social heart of the region for culinary outings and dining events. Visitors can sample wood-fired pizza and local culinary vendors at Maitland Social while enjoying shared indoor-outdoor seating options.

Which venues host independent film events and social gatherings?

Enzian Theater operates as a historic single-screen independent cinema and cultural anchor for film enthusiasts. The venue hosts arthouse film events, special screenings, and lively social meetups at the adjoining open-air Eden Bar throughout the calendar year.

Can visitors enjoy live music events near the lakeshore?

Lake Lily Park hosts outdoor musical events featuring acoustic performances alongside the active community market. The scenic park grounds provide relaxed green spaces for weekend listeners, families, and neighborhood strollers seeking pleasant outdoor environs in the district.

What community spaces feature local food hall events?

Maitland Social delivers a compact community food hall experience featuring diverse local culinary vendors and food events. Guests gather in shared indoor and outdoor seating areas to enjoy artisan dishes within a walkable neighborhood radius close to local retail spots.