Best events in
Leesburg

For events and things to do in Leesburg, VA, the scene is deeply rooted in its historic downtown and the surrounding wine country. The town's social calendar is marked by community traditions and a steady stream of live music. Beyond the historic center, modern developments and sprawling vineyards offer different atmospheres for entertainment.

Stroll through Historic Downtown Leesburg during the monthly Monthly art walk, when galleries, shops, and restaurants stay open late with special exhibits and live music.
Catch national touring acts, comedy shows, and tribute bands at the historic Tally Ho Theater, a restored Art Deco venue in the heart of downtown.
Explore Loudoun County's wine culture with tastings and events at scenic vineyards like Stone Tower Winery or Willowcroft Farm Vineyards.

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Popular in Leesburg

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Approach to Inflammation Health & Wellness Event

Today • 5:00 PM

Leesburg Volunteer Fire Company Banquet Hall

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Warrior Women - Self Defense Jiu-Jitsu

Today • 10:00 AM + 9 more

Mastery Jiu-Jitsu

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Riserva and Fumo - Volume II

Tomorrow • 6:00 PM

7 W Market St

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Ladies Night: Sip, Smoke & Paint!

Thu, Nov 5 • 7:00 PM

Rebellion Bourbon Bar & Kitchen

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Black Hoof Drag Bingo with Crimsyn featuring Crystal

Tue, Nov 17 • 7:00 PM

Black Hoof Brewing Company

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Loudoun Jazz Society Presents: A Saxophone Summit

Sat, Nov 21 • 7:30 PM

Leesburg Junction

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Leesburg Movement's Annual Mistletoe Market

Sat, Dec 5 • 11:00 AM

Courthouse Square

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Christmas Mommy & Me Chocolate Sculpture Workshop | Holiday Fun

Sun, Dec 13 • 10:00 AM

The Conche

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Approach to Inflammation Health & Wellness Event

Today • 5:00 PM

Leesburg Volunteer Fire Company Banquet Hall

Check ticket price on event

Warrior Women - Self Defense Jiu-Jitsu

Today • 10:00 AM + 9 more

Mastery Jiu-Jitsu

Check ticket price on event

Riserva and Fumo - Volume II

Tomorrow • 6:00 PM

7 W Market St

Check ticket price on event

Ladies Night: Sip, Smoke & Paint!

Thu, Nov 5 • 7:00 PM

Rebellion Bourbon Bar & Kitchen

Check ticket price on event

Black Hoof Drag Bingo with Crimsyn featuring Crystal

Tue, Nov 17 • 7:00 PM

Black Hoof Brewing Company

Check ticket price on event

Loudoun Jazz Society Presents: A Saxophone Summit

Sat, Nov 21 • 7:30 PM

Leesburg Junction

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Leesburg Movement's Annual Mistletoe Market

Sat, Dec 5 • 11:00 AM

Courthouse Square

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Christmas Mommy & Me Chocolate Sculpture Workshop | Holiday Fun

Sun, Dec 13 • 10:00 AM

The Conche

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Online Events

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(ONLINE) Women on the Move with Ann Patchett

Today • 11:30 AM EDT

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MENTORSHOP: Using Claude AI to Build a SaaS Site in about a Week

Tomorrow • 12:00 PM PDT

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Turn Your Ideas Into Income

Tomorrow • 10:00 AM EDT

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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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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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(ONLINE) Women on the Move with Ann Patchett

Today • 11:30 AM EDT

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MENTORSHOP: Using Claude AI to Build a SaaS Site in about a Week

Tomorrow • 12:00 PM PDT

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Turn Your Ideas Into Income

Tomorrow • 10:00 AM EDT

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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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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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This Weekend

Trunk Or Treat

Friday • 6:30 PM

The Church of Jesus Christ of Latter-day Saints

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Trunk or Treat at The Branch!

Saturday • 12:00 PM

The Branch

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Rust Library- Sahaja Yoga - Guided Meditatation

Saturday • 11:30 AM

Rust Library

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Silent Book Club Leesburg @ Birch Tree Books and Plants

Sunday • 5:00 PM

Birch Tree Books & Plants

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Trunk Or Treat

Friday • 6:30 PM

The Church of Jesus Christ of Latter-day Saints

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Trunk or Treat at The Branch!

Saturday • 12:00 PM

The Branch

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Rust Library- Sahaja Yoga - Guided Meditatation

Saturday • 11:30 AM

Rust Library

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Silent Book Club Leesburg @ Birch Tree Books and Plants

Sunday • 5:00 PM

Birch Tree Books & Plants

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From nearby cities

Ashburn, Dulles, Chantilly, VA Singles Event with Singles 30–49

Friday • 6:00 PM

Juleps Kentucky Tavern

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OODAcon and ChinaCon

Wed, Nov 4 • 7:30 AM

Hyatt Reston Town Center

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AWARD WINNING MARYLAND WINE-Governor's Cup Winners Celebration

Thu, Nov 5 • 5:30 PM

Windridge Vineyards

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The Black Tie Affair

Sat, Nov 7 • 7:00 PM

Aston Martin Washington D.C.

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Loudoun Symphony Youth Orchestra Fall Concert

Sun, Nov 8 • 4:00 PM

Stone Bridge High School

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Discover & Celebrate Your Inner Goddess!

Sat, Nov 14 • 10:00 AM

The Chase Club at Hotel Burg

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2027 NAVY PROCUREMENT OUTLOOK SUMMIT

Mon, Nov 16 • 7:00 AM

Carahsoft Conference & Collaboration Center

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LAI Generics: Advancing Innovation in Product Dev. & Regulatory Assessment

Tue, Dec 1 • 8:00 AM

The Universities at Shady Grove

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Ashburn, Dulles, Chantilly, VA Singles Event with Singles 30–49

Friday • 6:00 PM

Juleps Kentucky Tavern

Check ticket price on event

OODAcon and ChinaCon

Wed, Nov 4 • 7:30 AM

Hyatt Reston Town Center

Check ticket price on event

AWARD WINNING MARYLAND WINE-Governor's Cup Winners Celebration

Thu, Nov 5 • 5:30 PM

Windridge Vineyards

Check ticket price on event

The Black Tie Affair

Sat, Nov 7 • 7:00 PM

Aston Martin Washington D.C.

Check ticket price on event

Loudoun Symphony Youth Orchestra Fall Concert

Sun, Nov 8 • 4:00 PM

Stone Bridge High School

Check ticket price on event

Discover & Celebrate Your Inner Goddess!

Sat, Nov 14 • 10:00 AM

The Chase Club at Hotel Burg

Check ticket price on event

2027 NAVY PROCUREMENT OUTLOOK SUMMIT

Mon, Nov 16 • 7:00 AM

Carahsoft Conference & Collaboration Center

Check ticket price on event

LAI Generics: Advancing Innovation in Product Dev. & Regulatory Assessment

Tue, Dec 1 • 8:00 AM

The Universities at Shady Grove

Check ticket price on event

Points of Interest near Leesburg

Balls Bluff Battlefield Regional Park

Frequently asked questions about Leesburg

Where can I find live music events in Leesburg?

Tally Ho Theater is a primary venue for national touring acts and tribute bands. For a more casual setting, Loudoun Brewing Company hosts local musicians, and the Summer JAMS series brings free outdoor concerts to the Town Green.

What is the art scene like in Historic Downtown Leesburg?

The downtown Arts & Cultural District is centered around numerous independent art galleries. The monthly Leesburg's Monthly event is a great way to experience this scene, with late hours, special exhibits, and live music filling the streets.

Are there free events to attend in Leesburg?

Yes, Leesburg hosts several popular free community events. The Summer JAMS concert series offers free outdoor music, and the monthly Monthly art walk allows for gallery browsing without an admission fee in a lively atmosphere.

What are some family-friendly things to do in Leesburg?

Ida Lee Park Recreation Center frequently hosts community events and seasonal craft shows. The annual Leesburg Flower and Garden Festival also transforms downtown into a lively, family-friendly space with landscape displays and activities.

What are some good date night ideas in Leesburg, VA?

A classic Leesburg date could involve dinner downtown followed by a show at Tally Ho Theater. For a different vibe, the Village at Leesburg offers dinner, a movie at CMX Cinemas, and activities like bowling at Bowlero.

Which areas are best for food and drink events in Leesburg?

Historic Downtown is the hub for local flavor, from craft beer at Loudoun Brewing Company to restaurant specials during Monthly events. The surrounding area is also wine country, with vineyards like Stone Tower Winery offering tastings.

What kind of nightlife events does Leesburg offer?

Leesburg's nightlife centers on live entertainment and relaxed social settings. Evenings often involve catching a concert at Tally Ho Theater, enjoying trivia night at a brewery, or visiting bars in the walkable historic downtown.

How can I find outdoor events in the Leesburg area?

Many events take advantage of the town's public spaces and scenic surroundings. Look for the outdoor Summer JAMS concert series on the Town Green or explore the annual Leesburg Flower and Garden Festival, which fills the downtown streets.