Events and Things to Do in Leesburg, VA

Saturday, September 26

Featured

Loudoun Recovery Fest 2026

SEP

26

9:00 AM

Douglass Community Center, 407 E Market St, Leesburg, VA

Recovery Fest is Loudoun County’s annual event celebrating and supporting recovery from addiction to drugs and alcohol. This...

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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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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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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 20

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

  9101 Prince William St, Manassas

  
  

Tuesday, September 22

• What the Body Tells Us: Forensic Science at Mason's Outdoor Research Facility 7:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Wednesday, September 23

• Makerspace: Glowforge Fall Bookmark 6:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Thursday, September 24

• How to Become a U.S. Citizen 9:00 am

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• Essay Discussion Club 11:00 am

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  

Friday, September 25

• Yappy Hour 5:00 pm

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

  
  

Saturday, September 26

• Loudoun Recovery Fest 2026 9:00 am

  Douglass Community Center, 407 E Market St, Leesburg

  
  
• Rust Writing Group 3:00 pm

  Rust Library, 380 Old Waterford Rd NW, Leesburg

  
  
• Celebration of Life & Leadership Gala 6:00 pm

  The National Conference Center, 18665 Conference Ctr Dr, Leesburg

  
  
• The Reflex - Ultimate '80s Music 6:00 pm

  Tarara Summer Concert Series, 13648 Tarara Ln, Leesburg

  
  

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