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Best events in
Round Hill

For events and things to do in Round Hill, VA, the local scene is rooted in its agricultural heritage and Blue Ridge setting. Social life often revolves around the area's many wineries and farm breweries, which frequently feature live performances. Nearby towns like Purcellville and Leesburg expand the possibilities with bustling historic downtowns and monthly art walks.

The weekend rhythm often involves exploring the countryside, with many wineries and breweries like B Chord Brewery hosting live music.
Family-friendly activities are central, highlighted by the annual Round Hill Hometown Festival and weekly farmers' markets in Purcellville and Leesburg.
For art and culture, the Round Hill Arts Center offers workshops, while Leesburg's Monthly showcases local galleries and studios each month.

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HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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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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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg primary image

(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM 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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Thu, Nov 12 • 2:00 PM UTC

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How To Be Kind To Yourself - Shahroo Izadi primary image

How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism primary image

HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism primary image

HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD primary image

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg primary image

(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

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Witch hunts and real lives primary image

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 primary image

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 primary image

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Events near Round Hill

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Lucketts Fall Market primary image

Lucketts Fall Market

Fri, Oct 16 • 8:30 AM

Clarke County Ruritan Fairgrounds

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The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment primary image

The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment

Sat, Oct 17 • 8:00 PM

Clarion Inn Harpers Ferry-Charles Town

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

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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Hoedown 2026

Fri, Oct 23 • 5:00 PM

18297 Yellow Schoolhouse Rd

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2026 Loudoun Wine Awards Dinner primary image

2026 Loudoun Wine Awards Dinner

Fri, Oct 23 • 6:00 PM

Lansdowne Resort

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Botanical Watercolor - Transparent Flowers primary image

Botanical Watercolor - Transparent Flowers

Sun, Oct 25 • 2:00 PM

Sterling Hills Farm

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A Grave Misunderstanding: Murder Mystery Dinner at The Branch primary image

A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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Lucketts Fall Market primary image

Lucketts Fall Market

Fri, Oct 16 • 8:30 AM

Clarke County Ruritan Fairgrounds

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The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment primary image

The Appalachian Oddities Costume Ball ~ A Night of Strange Merriment

Sat, Oct 17 • 8:00 PM

Clarion Inn Harpers Ferry-Charles Town

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

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 primary image

Black Hoof Drag Bingo with Crimsyn featuring Jasmine Kennedie

Tue, Oct 20 • 7:00 PM

Black Hoof Brewing Company

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Hoedown 2026 primary image

Hoedown 2026

Fri, Oct 23 • 5:00 PM

18297 Yellow Schoolhouse Rd

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2026 Loudoun Wine Awards Dinner primary image

2026 Loudoun Wine Awards Dinner

Fri, Oct 23 • 6:00 PM

Lansdowne Resort

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Botanical Watercolor - Transparent Flowers primary image

Botanical Watercolor - Transparent Flowers

Sun, Oct 25 • 2:00 PM

Sterling Hills Farm

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A Grave Misunderstanding: Murder Mystery Dinner at The Branch primary image

A Grave Misunderstanding: Murder Mystery Dinner at The Branch

Thu, Oct 29 • 6:00 PM

The Branch

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Nearby cities

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National Harbor

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McLean

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Spring Ridge

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Leesburg

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Springfield

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Konterra

45 miles away

Manassas

31 miles away

Chantilly

24 miles away

Potomac

33 miles away

Hyattsville

46 miles away

Germantown

27 miles away

Winchester

21 miles away

Countryside

20 miles away

Washington

43 miles away

Arlington

41 miles away

Alexandria

44 miles away

Columbia

49 miles away

Silver Spring

41 miles away

North Bethesda

36 miles away

Reston

25 miles away

Fairfax

31 miles away

Tysons Corner

33 miles away

Bethesda

37 miles away

College Park

45 miles away

Hagerstown

35 miles away

Frederick

28 miles away

Gaithersburg

30 miles away

Rockville

33 miles away

Laurel

49 miles away

Vienna

32 miles away

National Harbor

47 miles away

McLean

34 miles away

Spring Ridge

27 miles away

Leesburg

12 miles away

Springfield

40 miles away

Konterra

45 miles away

Manassas

31 miles away

Chantilly

24 miles away

Potomac

33 miles away

Hyattsville

46 miles away

Germantown

27 miles away

Winchester

21 miles away

Countryside

20 miles away

Frequently asked questions about Round Hill

Where can I find live music events near Round Hill?

B Chord Brewery is a top spot for live music, featuring performances on its stage most weekends. Many other wineries and breweries throughout Loudoun County, like Good Spirit Farm, also host local musicians, offering a relaxed, rural setting.

What are the best family-friendly events in the area?

The region offers many all-ages activities, especially farm-based ones and community festivals. The annual Round Hill Hometown Festival is a major highlight, and the Purcellville and Leesburg farmers' markets are popular weekend outings.

Are there recurring art events to check out?

Leesburg's Monthly is a popular monthly event for exploring local art. On the monthly of each month, galleries and shops in historic downtown Leesburg host special exhibits, live music, and receptions for the community.

How can I find free events in the Round Hill area?

Free community events are common, particularly concerts and outdoor festivals. The Summer JAMS concert series on the Leesburg Town Green offers free outdoor music, and many live music performances at local breweries do not have a cover charge.

Is there much nightlife in or around Round Hill?

Nightlife in the area is relaxed and typically centers on breweries, wineries, and pubs. For a more active evening, nearby Purcellville and Leesburg have downtowns with restaurants that host trivia nights and live music.

What are some good date night ideas in the region?

A great date night could involve wine tasting at a scenic spot like Williams Gap Vineyard. Afterwards, head to historic downtown Leesburg or Purcellville for dinner and to catch some live music at a local brewery.

Which neighborhoods offer the best food and drink scenes?

Purcellville's downtown offers a classic small-town feel with several breweries and restaurants. For more variety, historic Leesburg has a bustling center with a wider array of dining and drinking establishments, especially lively during its monthly Monthly event.

Where's a good spot for outdoor events?

Franklin Park in Purcellville is a great destination for outdoor activities and hosted performances. Beyond the park, many wineries and breweries like B Chord Brewery use their spacious rural settings for outdoor music events and gatherings.