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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Grand Opening: Bricks & Minifigs Loudoun! Free Family Celebration.

Saturday • 11:00 AM

210 B Fort Evans Rd NE

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Loudoun Thrift October Mobile Thrift Tour

Saturday • 9:00 AM

Meetup at First Stop Blue Ridge Care Thrift

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An Evening with Chef Patrick O'Connell: A Celebration of His New Memoir

Mon, Oct 19 • 5:00 PM

Hotel Burg

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Black Hoof Drag Bingo with Crimsyn featuring Jasmine Kennedie

Tue, Oct 20 • 7:00 PM

Black Hoof Brewing Company

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Village at Leesburg 2026 Monster Mash

Sat, Oct 24 • 1:00 PM

Village at Leesburg

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Approach to Inflammation Health & Wellness Event

Tue, Oct 27 • 5:00 PM

Leesburg Volunteer Fire Company Banquet Hall

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A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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Loudoun Jazz Society Presents: A Saxophone Summit

Sat, Nov 21 • 7:30 PM

Leesburg Junction

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Grand Opening: Bricks & Minifigs Loudoun! Free Family Celebration.

Saturday • 11:00 AM

210 B Fort Evans Rd NE

Check ticket price on event

Loudoun Thrift October Mobile Thrift Tour

Saturday • 9:00 AM

Meetup at First Stop Blue Ridge Care Thrift

Check ticket price on event

An Evening with Chef Patrick O'Connell: A Celebration of His New Memoir

Mon, Oct 19 • 5:00 PM

Hotel Burg

Check ticket price on event

Black Hoof Drag Bingo with Crimsyn featuring Jasmine Kennedie

Tue, Oct 20 • 7:00 PM

Black Hoof Brewing Company

Check ticket price on event

Village at Leesburg 2026 Monster Mash

Sat, Oct 24 • 1:00 PM

Village at Leesburg

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Approach to Inflammation Health & Wellness Event

Tue, Oct 27 • 5:00 PM

Leesburg Volunteer Fire Company Banquet Hall

Check ticket price on event

A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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Loudoun Jazz Society Presents: A Saxophone Summit

Sat, Nov 21 • 7:30 PM

Leesburg Junction

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Online Events

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A Norman stitch-up? The story behind the Bayeux Tapestry

Tomorrow • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

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Perfectionnement en programmation Python [en ligne, PYT102]

Thu, Oct 15 • 9:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 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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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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A Norman stitch-up? The story behind the Bayeux Tapestry

Tomorrow • 7:30 PM GMT+1

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AI Kids Music Video Studio: Produce Black Nursery Rhyme for YouTube

Thursday • 6:00 PM EDT

Check ticket price on event

Perfectionnement en programmation Python [en ligne, PYT102]

Thu, Oct 15 • 9:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 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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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Food & Drink events

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An Evening with Chef Patrick O'Connell: A Celebration of His New Memoir

Mon, Oct 19 • 5:00 PM

Hotel Burg

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A Sicilian Wine Dinner with Cantine Ermes

Wed, Oct 21 • 6:00 PM

7 W Market St

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Chocolate Boo Bash: A Mommy & Me Sculpting Workshop

Sat, Oct 24 • 10:00 AM

The Conche

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A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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An Evening with Chef Patrick O'Connell: A Celebration of His New Memoir

Mon, Oct 19 • 5:00 PM

Hotel Burg

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A Sicilian Wine Dinner with Cantine Ermes

Wed, Oct 21 • 6:00 PM

7 W Market St

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Chocolate Boo Bash: A Mommy & Me Sculpting Workshop

Sat, Oct 24 • 10:00 AM

The Conche

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A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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Business & Professional events

Hiring Event with Gate Gourmet

Thu, Oct 15 • 10:00 AM + 7 more

Loudoun Workforce Resource Center

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From Ownership to Opportunity: Connecting Business and Personal Wealth

Wed, Oct 21 • 5:00 PM

Shutters on King

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Strategic Business Planning Retreat

Thu, Nov 5 • 9:00 AM

Hotel Burg

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Hiring Event with Gate Gourmet

Thu, Oct 15 • 10:00 AM + 7 more

Loudoun Workforce Resource Center

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From Ownership to Opportunity: Connecting Business and Personal Wealth

Wed, Oct 21 • 5:00 PM

Shutters on King

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Strategic Business Planning Retreat

Thu, Nov 5 • 9:00 AM

Hotel Burg

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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.