Leesburg Airshow
The Leesburg Airshow takes flight on Saturday, Sept. 27, from 11 a.m.-4 p.m. at Leesburg Executive Airport, located at 520 Evergreen Mills Road, Leesburg, offering thrilling aerial performances, fascinating tarmac displays, and family-friendly activities for all ages, with antique and modern planes and helicopters on display, including the historic Douglas C-54 Skymaster “Spirit of Freedom,” a flying museum from the Berlin Airlift that guests can tour, plus Smithsonian National Air and Space Museum Explainers on site with interactive demonstrations, hands-on science, and technology activities, alongside festival food, local craft beer, and inflatable slides, making this annual community celebration a must-see aviation event blending history, education, and high-flying fun.
Celebrate Purcellville!
Celebrate Purcellville Fall Festival returns Saturday, Oct. 18, from 2–5 p.m. in Dillon’s Woods, inviting the community to enjoy carnival games, an obstacle course, live music, food and beverage vendors, and opportunities to collect Celebrate Purcellville Passport stickers for a chance to win prizes, with eligibility for participants who earn at least 20 stickers from local businesses, 6 codes from the scavenger hunt, or 6 answers from the nature trivia walk, while prizes donated by participating businesses will be awarded to attendees present at the event, which caps off a week-long celebration hosted by the Town of Purcellville and its Parks and Recreation Advisory Board.
Monday, Sept. 22
Annual Golf Tournament
WHEN: 9 a.m.
WHERE: Raspberry Falls Golf & Hunt Club, 41601 Raspberry Drive, Leesburg
Tuesday, Sept. 23
Storytime Gone Wild & Nature Walk – Hummingbirds!
WHEN: 9:30-10:30 a.m.
WHERE: Visitor’s Center, 21085 The Woods Road, Leesburg
Launch Your Business in Loudoun County: A Practical Step-by-Step Guide to Starting and Growing Your Small Business
WHEN: 10-11 a.m.
WHERE: Workforce Resource Center, 705 E. Market St., Suite E, Leesburg
Sacred Salon : Things That Matter • a dialogue
WHEN: 7:30-10 p.m.
WHERE: Temple in the Trees, 106 Calvary Court Southeast, Leesburg
PRICE: $55
Wednesday, Sept. 24
Navigating LinkedIn for New Users Workshop
WHEN: 10-11:30 a.m.
WHERE: Workforce Resource Center, 705 E. Market St., Suite E, Leesburg
Balanced Living with Diabetes
WHEN: 1-3 p.m.
WHERE: Sterling Library, 22330 S. Sterling Blvd., Suite A117, Sterling
Lazy Book Club September 2025 Meetup
WHEN: 5-7 p.m.
WHERE: Leesburg Public House, 962 Edwards Ferry Road NE, Leesburg
Thursday, Sept. 25
Low Cost Vaccination & Microchip Clinic
WHEN: 9-11 a.m.
WHERE: Loudoun County Animal Services, 42225 Adoption Drive, Leesburg
PRICE: $10-15
Peaceful Moon Yoga
WHEN: 6-7 p.m.
WHERE: Susan Green Living, 5 N. King St., Leesburg
Music Bingo: Country
WHEN: 7 p.m.
WHERE: The Branch, 49 Catoctin Cir SE, Leesburg
Friday, Sept. 26
LVFC Big House Classic Golf Tournament
WHEN: 11 a.m.
WHERE: Raspberry Falls Golf & Hunt Club, 41601 Raspberry Drive, Leesburg
Music in the Meadow – Summer Concert Series
WHEN: 6-8 p.m.
WHERE: Great Meadow, 5089 Old Tavern Road, The Plains
Saturday, Sept. 27
Rokeby Community Festival
WHEN: 10 a.m.-4 p.m.
WHERE: 8538 Mill Reef Road, Upperville
PRICE: $0-10
Triple Threat! Chocolate, Cheese, and Wine at Little Washington Winery
WHEN: 11 a.m.-1 p.m.
WHERE: Little Washington Winery, 72 Christmas Tree Lane, Washington
PRICE: $60
Monday, Sept. 29
30 Second Commercial Workshop
WHEN: 10 a.m.-12:30 p.m.
WHERE: Workforce Resource Center, 705 E. Market St., Suite E, Leesburg
Tuesday, Sept. 30
Resume Writing Lab 101 Workshop
WHEN: 9 a.m.-Noon
WHERE: Workforce Resource Center, 705 E. Market St., Suite E, Leesburg
Saturday, Oct. 4
Warrenton Fall Festival
WHEN: 10 a.m.-4 p.m.
WHERE: Main St., Warrenton
37th Annual Leesburg Car Show
WHEN: Noon-4 p.m.
WHERE: 21000 Education Ct, Ashburn
Celebrate the Spirit of Dashain and Tihar
WHEN: Noon-10 p.m.
WHERE: One Loudoun, 20280 Exchange St., Ashburn
PRICE: $15
Sunday, Oct. 5
Nomini Bay Oyster Festival
WHEN: Noon-5 p.m.
WHERE: Dirt Farm Brewing, 18701 Foggy Bottom Road, Bluemont
CCH Cornhole Classic
WHEN: 2-5 p.m.
WHERE: Lost Rhino Brewing Company, 21730 Red Rum Road, #142, Ashburn
PRICE: $0-100
Saturday, Oct. 11
Town of Remington Fall festivals
WHEN: 10 a.m.-4 p.m.
WHERE: Main St., Remington
Virginia Fall Races After Party
WHEN: 11 a.m.-9:30 p.m.
WHERE: Lost Barrel Brewing, 36138 Little River Turnpike, Middleburg
Sunday, Oct. 12
Wine Blending Lab at Little Washington Winery
WHEN: 2-3:30 p.m.
WHERE: Little Washington Winery, 72 Christmas Tree Lane, Washington
PRICE: $60
Saturday, Oct. 18
The Ladies Board 86th Annual Rummage Sale
WHEN: 10 a.m.-4 p.m.
WHERE: 17558 Dry Mill Road, Leesburg
PRICE: $56-86
Reach the Roots: Kinloch Farm Tour
WHEN: 11 a.m.-2 p.m.
WHERE: 5313 Hopewell Road, The Plains
Notes of Hope Gala
WHEN: 5:30-10 p.m.
WHERE: The Lodge at Hanson Park, 23394 Endeavor Drive, Aldie
Sunday, Oct. 19
Discover Austrian Wines, at Little Washington Winery
WHEN: 2-3:30 p.m.
WHERE: Little Washington Winery, 72 Christmas Tree Lane, Washington
PRICE: $60
Touch-a-truck
WHEN: 3-6 p.m.
WHERE: Lost Barrel Brewing, 36138 Little River Turnpike, Middleburg
Sunset in the Field 2025
WHEN: 3-7 p.m.
WHERE: 36276 Mountville Road, Middleburg
PRICE: $110
