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Best events in
Delaplane

With its unhurried pace and focus on outdoor activities, there are plenty of events and things to do in Delaplane, VA. The local culture revolves around its expansive country estates, numerous wineries, and a strong equestrian heritage. From daytime agricultural festivals to quiet evenings perfect for stargazing, the area offers a relaxed alternative to city life.

Spend an afternoon exploring the rolling hills of the Middleburg American Viticultural Area, where local wineries like Barrel Oak Winery, Blue Valley Vineyard, and Delaplane Cellars host tastings and social gatherings.
Enjoy outdoor pursuits at Sky Meadows State Park, a designated Dark Sky Park, or visit a local spot like Hollin Farms for seasonal pick-your-own produce.
Catch a recurring stand-up show at Three Fox Vineyards & Brewery, which hosts the Next Stop Comedy series.

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Thu, Oct 15 • 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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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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AI Animation Studio: Create Kids' Cartoons

Tomorrow • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism primary image

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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Perfectionnement en programmation Python [en ligne, PYT102] primary image

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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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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(ONLINE) Women on the Move with Ann Patchett primary image

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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The MI5 Archive: Official Secrets primary image

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 primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Events near Delaplane

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Bear Chase Brewing Company

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October Bird Walk

Friday • 8:00 AM

Blandy Experimental Farm/State Arboretum of Virginia

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Lucketts Fall Market

Fri, Oct 16 • 8:30 AM

Clarke County Ruritan Fairgrounds

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Hoedown 2026

Fri, Oct 23 • 5:00 PM

18297 Yellow Schoolhouse Rd

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Wicked Fun Mahjong Open Play at Great Mane Brewery- Haymarket

Mon, Oct 26 • 6:30 PM

Great Mane Brewery

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Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc

Sat, Nov 14 • 6:00 PM

Bluemont Vineyard

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Sat, Nov 21 • 10:00 AM

Gathering Springs Farm, Sam Fred Road, Middleburg, VA, USA

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Sunday Mahjong Open Play at Three Fox Vineyards and Brewery primary image

Sunday Mahjong Open Play at Three Fox Vineyards and Brewery

Sun, Dec 13 • 12:00 PM

Three Fox Vineyards & Farm Brewery

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Mahjong Beginners Class at Bear Chase!

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Bear Chase Brewing Company

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October Bird Walk primary image

October Bird Walk

Friday • 8:00 AM

Blandy Experimental Farm/State Arboretum of Virginia

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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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Hoedown 2026 primary image

Hoedown 2026

Fri, Oct 23 • 5:00 PM

18297 Yellow Schoolhouse Rd

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Wicked Fun Mahjong Open Play at Great Mane Brewery- Haymarket

Mon, Oct 26 • 6:30 PM

Great Mane Brewery

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Pours to Explore Tasting Series: Sauvignon Blanc & Cabernet Franc

Sat, Nov 14 • 6:00 PM

Bluemont Vineyard

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Thanksgiving Beeswax Bundle primary image

Thanksgiving Beeswax Bundle

Sat, Nov 21 • 10:00 AM

Gathering Springs Farm, Sam Fred Road, Middleburg, VA, USA

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Sunday Mahjong Open Play at Three Fox Vineyards and Brewery primary image

Sunday Mahjong Open Play at Three Fox Vineyards and Brewery

Sun, Dec 13 • 12:00 PM

Three Fox Vineyards & Farm Brewery

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Frequently asked questions about Delaplane

What are some food and drink events in Delaplane?

The region's many wineries offer frequent tastings and events. Places like Barrel Oak Winery, Delaplane Cellars, and Blue Valley Vineyard are popular spots. For local produce, check out The FarmFarm Farmers' Market or seasonal activities at Messick's Farm Market.

Where can I find comedy shows in the Delaplane area?

Three Fox Vineyards & Brewery hosts a recurring stand-up comedy event. The Next Stop Comedy series brings a lineup of comedians to the vineyard's scenic setting. It’s a popular choice for an evening of entertainment combined with local craft beverages.

Are there family-friendly things to do in Delaplane?

Yes, the area offers many family-oriented agricultural activities. You can go for seasonal pick-your-own produce at Hollin Farms. Sky Meadows State Park also hosts the annual Delaplane Strawberry Festival and a Fall Foliage Festival with activities for all ages.

How can I enjoy the outdoors for a date night in Delaplane?

Stargazing at Sky Meadows State Park is a unique date night activity. As a designated Dark Sky Park, it offers incredible views of the night sky, far from city lights. The park is an ideal spot for a quiet, romantic evening in nature.

What kind of annual festivals happen near Delaplane?

The area hosts several beloved annual festivals celebrating local culture and seasons. Sky Meadows State Park is home to the Delaplane Strawberry Festival. Nearby Warrenton also has the Old Town Warrenton Fall Festival and the Fauquier County Cultural Heritage Festival.

Are there live music events in Delaplane?

Yes, local wineries frequently feature live music events, especially on weekends. Venues such as Barrel Oak Winery & Brewery provide a relaxed atmosphere where visitors can enjoy local wine or beer accompanied by musical performances in a scenic country setting.

What's the nightlife scene like in Delaplane?

Delaplane's nightlife is generally quiet and centered on relaxed experiences. Instead of clubs, evenings feature winery events or stargazing at Sky Meadows State Park. For a unique sporting event, Great Meadow Polo has matches on some evenings.

Can I find local farmers' markets or free events around Delaplane?

Yes, you can browse local goods at The FarmFarm Farmers' Market. For free activities, enjoy hiking or picnicking at Sky Meadows State Park. The area’s scenic roads are also perfect for a drive to see the historic countryside and fall foliage.