Events and Things to Do in Ashburn, VA

Sunday, September 27

Featured

Hail to the Trail!

SEP

27

1:00 PM

Chapman DeMary Trail, 355 N Hatcher Ave, Purcellville, VA

Bring your family and friends to the 14th annual Hail to the Trail event at the Chapman DeMary Trail on September 27 from 1 to...

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Thursday, October 1

Featured

Autumn in Bloom Thursday, October 1, 11 a.m. - 3 p.m.

OCT

1

11:00 AM

Hope Flower Farm And Winery, 40905 Stumptown Rd, Waterford, VA

Join The Garden Club of Fairfax for a special day at the beautiful Hope Flower Farm and Winery. Enjoy an inspiring presentation...

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Friday, October 2

Featured

82nd Waterford Fair

OCT

2

10:00 AM

Waterford Foundation, 40222 Fairfax St, Waterford, VA

October 2-4, 2026   Come experience an autumn celebration of Americana at the Waterford Fair, recognized as one of the Sunshine...

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Sunday, October 4

Featured

LC3' Pints 4 Paws Celebration and Fundraiser for Community Cats

OCT

4

12:00 PM

Vanish Farmwoods Brewery, 42245 Black Hops Ln, Leesburg, VA

Join us for our 8th Annual Pints 4 Paws celebration and fundraiser at Vanish Brewery in Lucketts Virginia! Proceeds benefit...

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Saturday, October 10

Featured

Marian Homes, Inc. 2026 Casino Night Gala

OCT

10

7:00 PM

The Tower Club Tysons, 8000 Towers Crescent Dr, Vienna, VA

Join Marian Homes, Inc. for our 2026 Casino Night Gala on Saturday, October 10, at the beautiful Tower Club in Tysons Corner!...

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Sunday, September 27

• Hail to the Trail! 1:00 pm

  Chapman DeMary Trail, 355 N Hatcher Ave, Purcellville

  
  
• Ghost Doctors'UFO Adventure At The Smithsonian Air and Space Udvar-Hazy Center! 3:15 pm

  14390 Air and Space Museum Pkwy, Chantilly

  
  

Thursday, October 1

• Autumn in Bloom Thursday, October 1, 11 a.m. - 3 p.m. 11:00 am

  Hope Flower Farm And Winery, 40905 Stumptown Rd, Waterford

  
  

Friday, October 2

• 82nd Waterford Fair 10:00 am

  Waterford Foundation, 40222 Fairfax St, Waterford

  
  

Sunday, October 4

• LC3' Pints 4 Paws Celebration and Fundraiser for Community Cats 12:00 pm

  Vanish Farmwoods Brewery, 42245 Black Hops Ln, Leesburg

  
  
• Donut Sunday @ Saint Theresa Church 8:00 am

  Saint Theresa Catholic Church, 21370 St Theresa Ln, Ashburn

  
  

Saturday, October 10

• Marian Homes, Inc. 2026 Casino Night Gala 7:00 pm

  The Tower Club Tysons, 8000 Towers Crescent Dr, Vienna

  
  

Sunday, October 11

• Pancake Breakfast & Halloween Fun at Ashburn Volunteer Fire & Rescue! 8:00 am

  43765 Ashburn Volunteer Plz, Ashburn, VA

  
  
• SUNDAY RECHARGE: Give Yourself 21 Minutes 10:00 am

  Ashburn Library, 43316 Hay Rd, Ashburn

  
  

Saturday, October 17

• 7th Annual Live4Lane Memorial 5K 8:00 am

  Lowes Island Community Center, 47620 Saulty Dr, Sterling

  
  
• 7th Annual Live4Lane Memorial 5K & Resource Fair 8:00 am

  Lowes Island Community Center, 47620 Saulty Dr, Sterling

  
  
• Fall Festival by Joshua's Hands 10:00 am

  Historic Walnut Creek Farm, 39550 Meadowlark Dr, Hamilton

  
  

Sunday, October 25

• Lobstalicious 12:30 pm

  Lark Brewing Co., 24205 James Monroe Hwy, Aldie

  
  
• Lobstahlicious at Lark 12:30 pm

  24205 James Monroe Hwy, Aldie

  
  

Friday, October 30

• Comedy Showcase Benefitting Gift of Adoption 5:30 pm

  Solace Brewing Company, 42615 Trade W Dr, Sterling

  
  

Saturday, October 31

• Loudoun Symphony Presents Halloween at Hogwarts 3:00 pm

  Stone Bridge High School, 43100 Hay Rd, Ashburn

  
  
• Holla-Ween: Makes Me Wanna Holla! Day Party 4:00 pm

  46700 Middlefield Dr Sterling, VA 20165

  
  

Saturday, November 7

• Comedy for a Cause: Supporting Our Veterans One Laugh at a Time 5:00 pm

  Compass & Anchor Club, 401 W Holly Ave, Sterling

  
  

Saturday, November 14

• DMV Chocolate and Coffee Festival ~ Virginia Edition 10:00 am

  Dulles Town Center, 21100 Dulles Town Cir, Sterling

  
  

Sunday, January 10, 2027

• *Extended Donation Date* Loudoun County Combined Fire and Rescue Coat Drive to Benefit Mobile Hope 12:59 pm

  Loudoun County Fire and Rescue, 801 Sycolin Rd, Leesburg