Best events in
Longwood

There is no shortage of community-focused events and things to do in Longwood, FL. Much of the city's social life revolves around the walkable historic downtown, with Reiter Park serving as a central hub for gatherings. The atmosphere is often relaxed and family-friendly, with local breweries and bars providing casual evening entertainment.

A typical weekend can begin with a morning trip to the weekly Longwood Farmers Market in Reiter Park for a classic local experience.
Find a variety of weekly entertainment, from trivia and BINGO nights at Hourglass Brewing to karaoke at Historic Bar Room.
Look for recurring community events in the historic downtown district, such as the monthly Downtown Longwood Cruise-in Car Show or the quarterly Battle of the Food Trucks.

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Popular in Longwood

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HEARTFULNESS MEDITATION ORLANDO

Tomorrow • 9:00 AM + 11 more

256 Rangeline Rd

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Space on Tap: When We Find Them First Contact Party

Thursday • 6:00 PM

Hourglass Brewing

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Scare Away Hunger 10/17/26

Sat, Oct 17 • 9:00 AM

U.S. Hunger (Formerly Feeding Children Everywhere)

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Denim & Black Experience

Sat, Oct 17 • 6:00 PM

323 N Ronald Reagan Blvd

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Fall Festival Open House at Kiddie Academy of Longwood-Lake Mary

Fri, Oct 23 • 5:30 PM

Kiddie Academy of Longwood-Lake Mary

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House of Sploot Sourdough Focaccia Class

Fri, Oct 23 • 6:00 PM

House of Sploot Pet Shop

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GSI: Geriatric & Special Needs Scene Investigation

Fri, Oct 23 • 9:00 AM + 6 more

1024 Florida Central Pkwy

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Monthly Orlando Women in Business Longwood

Wed, Nov 4 • 11:30 AM + 1 more

Ali Baba House of Kabob

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HEARTFULNESS MEDITATION ORLANDO

Tomorrow • 9:00 AM + 11 more

256 Rangeline Rd

Check ticket price on event

Space on Tap: When We Find Them First Contact Party

Thursday • 6:00 PM

Hourglass Brewing

Check ticket price on event

Scare Away Hunger 10/17/26

Sat, Oct 17 • 9:00 AM

U.S. Hunger (Formerly Feeding Children Everywhere)

Check ticket price on event

Denim & Black Experience

Sat, Oct 17 • 6:00 PM

323 N Ronald Reagan Blvd

Check ticket price on event

Fall Festival Open House at Kiddie Academy of Longwood-Lake Mary

Fri, Oct 23 • 5:30 PM

Kiddie Academy of Longwood-Lake Mary

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House of Sploot Sourdough Focaccia Class

Fri, Oct 23 • 6:00 PM

House of Sploot Pet Shop

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GSI: Geriatric & Special Needs Scene Investigation

Fri, Oct 23 • 9:00 AM + 6 more

1024 Florida Central Pkwy

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Monthly Orlando Women in Business Longwood

Wed, Nov 4 • 11:30 AM + 1 more

Ali Baba House of Kabob

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Online Events

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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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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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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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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Health & Wellness events

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Fascia Freedom: Creating More Ease Through Movement & Body Awareness

Today • 1:30 PM

Magnolia Yoga & Wellness Center

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GSI: Geriatric & Special Needs Scene Investigation

Fri, Oct 23 • 9:00 AM + 6 more

1024 Florida Central Pkwy

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Pie Party - Palmer Natural Health

Sat, Nov 14 • 4:00 PM

Palmer Natural Health

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FREE Health & Wellness Expo 2027: Elevate Your Well-Being

Sat, Feb 20 • 11:00 AM

Northland Church

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Fascia Freedom: Creating More Ease Through Movement & Body Awareness

Today • 1:30 PM

Magnolia Yoga & Wellness Center

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GSI: Geriatric & Special Needs Scene Investigation

Fri, Oct 23 • 9:00 AM + 6 more

1024 Florida Central Pkwy

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Pie Party - Palmer Natural Health

Sat, Nov 14 • 4:00 PM

Palmer Natural Health

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FREE Health & Wellness Expo 2027: Elevate Your Well-Being

Sat, Feb 20 • 11:00 AM

Northland Church

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From nearby cities

6th Annual Star 94.5 Heart & Soul Music Festival

Today • 4:00 PM

Apopka Amphitheater

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REWIND ⏪: Orlando’s #1 Throwback Block Party | 90s, 2000s & Early 2010s ✨

Sat, Oct 17 • 1:00 PM

Wall Street Plaza

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LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

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It's A 2000's (Halloween) Party: Orlando

Fri, Oct 23 • 10:00 PM

Celine Orlando

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R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

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GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Sat, Oct 31 • 10:00 AM

Wall Street Plaza

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Jesus 26

Thu, Dec 3 • 7:00 PM

Addition Financial Arena

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Orlando : One Love Festival

Sat, Dec 12 • 3:00 PM

Festival Park Orlando

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6th Annual Star 94.5 Heart & Soul Music Festival

Today • 4:00 PM

Apopka Amphitheater

Check ticket price on event

REWIND ⏪: Orlando’s #1 Throwback Block Party | 90s, 2000s & Early 2010s ✨

Sat, Oct 17 • 1:00 PM

Wall Street Plaza

Check ticket price on event

LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

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It's A 2000's (Halloween) Party: Orlando

Fri, Oct 23 • 10:00 PM

Celine Orlando

Check ticket price on event

R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

Check ticket price on event

GOOD MORNING, HERE’S BREAKFAST: CEREAL KILLER (Halloween Edition)

Sat, Oct 31 • 10:00 AM

Wall Street Plaza

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Jesus 26

Thu, Dec 3 • 7:00 PM

Addition Financial Arena

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Orlando : One Love Festival

Sat, Dec 12 • 3:00 PM

Festival Park Orlando

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Points of Interest near Longwood

Spring Hammock Preserve

Frequently asked questions about Longwood

Where can I find free events in Longwood?

The Longwood Community Building is a great place to start for free activities. It hosts events like the monthly Senior Matinee, and many gatherings in adjacent Reiter Park are also free to attend, including the Downtown Longwood Cruise-in Car Show.

What are some family-friendly things to do?

Reiter Park offers many family-friendly activities centered around community events. The park hosts the weekly Longwood Farmers Market and is a great spot for outdoor fun. For a unique outing, check out the monthly classic car show in the historic district.

Are there any nightlife events in historic downtown Longwood?

Yes, downtown Longwood offers a casual and relaxed nightlife scene. Local spots like Hourglass Brewing host weekly trivia and BINGO nights, while Historic Bar Room provides recurring live music and karaoke events for a laid-back evening with the community.

How can I experience the local food and drink scene?

Hourglass Brewing is a popular spot to sample local craft beer and enjoy a social atmosphere. For more variety, look for the quarterly Battle of the Food Trucks event. The weekly Longwood Farmers Market also features local food vendors.

Which venues host outdoor events?

Reiter Park is the primary venue for outdoor events in Longwood. This central community space regularly hosts the weekly Longwood Farmers Market and other large gatherings. The historic downtown district also hosts the monthly Cruise-in Car Show.

Does Longwood have any recurring art events?

Yes, the city celebrates local creativity with the annual Longwood Arts and Crafts Festival. This event showcases a wide range of local artists and makers. The historic downtown setting provides a charming backdrop for the festival.

What kind of live music events happen in Longwood?

Local bars are the main spots for finding live music in Longwood. The family-owned Historic Bar Room frequently features live music acts as part of its recurring entertainment, creating a casual and intimate atmosphere for enjoying local talent.

What's a good idea for a casual date night in Longwood?

A fun date night could involve a visit to Hourglass Brewing for trivia or BINGO. The brewery also has arcade games for a playful vibe. Alternatively, checking out live music or karaoke at the Historic Bar Room offers another great local option.