Events and Things to Do in Leesburg, 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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Saturday, September 26

• Ghost Doctors' Chilling Ghost Hunting Adventure in Historic Old Town Manassas! 8:00 pm

  9101 Prince William St, Manassas

  
  

Sunday, September 27

• Hail to the Trail! 1:00 pm

  Chapman DeMary Trail, 355 N Hatcher Ave, Purcellville

  
  
• HSLC Adoption Event 12:00 pm

  Petco, 1031 Edwards Ferry Rd NE, Leesburg

  
  
• Wine and Pastry Pairing with Fleen's 2:00 pm

  October One Vineyard Wine Tasting Shop, 7 Loudoun St SW, Leesburg

  
  
• Dog Man Funfest 3:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Monday, September 28

• Memorable College Essays 6:00 am

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• Art at the Library for Kids - Henri Matisse 4:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• DIY Adults: Autumn Napkin Stamping 7:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Wednesday, September 30

• Adult Book Club - And Then There Were None by Agatha Christie 7:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

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

  
  
• Citizenship Preparation 7:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Friday, October 2

• 82nd Waterford Fair 10:00 am

  Waterford Foundation, 40222 Fairfax St, Waterford

  
  

Saturday, October 3

• DIY Teens and Adults: UV Resin Crafts 2:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Sunday, October 4

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

  Vanish Farmwoods Brewery, 42245 Black Hops Ln, Leesburg

  
  

Monday, October 5

• B-Movie Club: Ghoulies 6:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Tuesday, October 6

• Makerspace: Design a Mug 2:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Wednesday, October 7

• Makerspace: Glowforge 101 11:00 am

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• Meet Your Neighbor 2:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• SciFi/Fantasy Book Club - All Systems Red by Martha Wells 6:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Thursday, October 8

• Citizenship Preparation 7:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg