Friday is a student holiday, which makes this a four-day weekend rather than three. This is a longer issue than usual, because four days is a lot of days. The Scottish Games take Great Meadow for both Saturday and Sunday, their 52nd year, and parking costs nothing. Monday alone has a free car show, a parade, a waterpark on its last day and live music at a vineyard. Summer signs off in stages: the last Summer Strings night, Hook with a live orchestra at Wolf Trap, and the pools that close Monday evening.
Young kids: Family Fest takes the Village at Leesburg on Saturday, noon to four. Free, and so is the parking.
A couple: the DC Improv brings five comics to the Tally Ho on Friday. From $28, and the two-tops have gone.
Bring the kids for free: LoCo Fest at 868 Estate on Sunday, fifteen bands, noon to nine. Sixteen and under get in for nothing, and advance tickets stop Saturday.
Staying in Ashburn: the last Summer Strings night of the season, Friday on the One Loudoun park lawn. Free, 6 to 9, bring a chair.
The one to decide today: Squeeze, Adam Ant and Haircut 100 at Wolf Trap tomorrow night. Lawn is $62.50 and you can carry in your own cooler, wine included.
Sat 9/5 and Sun 9/6, 9 a.m.–6 p.m. · $25 a day, $40 the weekend; kids 6–12 $5 Saturday, free Sunday · ~40 min, 5089 Old Tavern Rd, The Plains · All ages
Cat Bingo at Vanish, and the proceeds go to rescue: the brewery runs it the first Thursday of every month with gift-card prizes, right up to the 8 o'clock close. The money goes to its trap-neuter-return and kitten rescue work.
Thu 9/3, 5:30–8 p.m. · No admission price posted · ~30 min, 42245 Black Hops Lane, Leesburg · All ages
Squeeze, Adam Ant and Haircut 100 on one Thursday bill: Wolf Trap puts three British new-wave acts on the Filene Center stage. Wolf Trap still lets you carry in your own food and drink, alcohol included, so a cooler on the lawn is the cheap way to do it. Chairs go at the top only.
Thu 9/3, 7:30 p.m., gates 6 p.m. · Lawn $62.50, seats $73–$106, fees included · ~30 min, Filene Center, 1551 Trap Rd, Vienna · Big kids and up
Herndon's free Friday concert hits its 500th show: Friday Night Live puts Shake the Room on the Town Green 6:30 to 10, and the series counts this as its 500th scheduled night. Free, outdoors, no ticket. The season was extended, so this isn't the last one; that's the 11th.
Fri 9/4, 6:30–10 p.m. · Free · ~20 min, Herndon Town Green · All ages
The last Summer Strings night of the summer: One Loudoun closes a series that has run every Friday since June 5. Richard Walton plays the park lawn off Exchange Street, past Endicott. Bring a chair.
Fri 9/4, 6–9 p.m. · Free · In Ashburn, One Loudoun Park · All ages
Loudoun United's community night, and $10 gets you in: the club hosts Colorado Springs with a Kids Zone, a high-five tunnel for ages 5 to 14 and autographs after the whistle. Gates an hour before kickoff, so there's time for the kids' side of it. A teenager can skip all that and just watch the match.
Fri 9/4, gates 6 p.m., kickoff 7 p.m. · $10–$72, fees included · ~20 min, Segra Field, 42095 Loudoun United Dr, Leesburg · All ages
Five comics at the Tally Ho, and the good tables have gone: the DC Improv brings a showcase hosted by Jack Coleman. Balcony four-tops start at about $28, and every two-top has already gone — so book tonight, not Friday.
Fri 9/4, 7 p.m., doors 6:30 · $28–$43, fees included · ~25 min, 19 W Market St SW, Leesburg · All ages
A 70s double bill at Tarara, and the gates open an hour early: the concert series has The Darby Brothers at 6 and Super Trans AM from 7:30, with an hour before that to set up chairs. Parking is free. Note the winery on the property has closed to the public; the concert series is what still runs there.
Sat 9/5, gates 5 p.m., music 6–9:30 p.m. · $20 advance, $25 door; $10 under 21 · ~25 min, 13648 Tarara Lane, Leesburg · All ages
Blackberry Smoke's 25th-anniversary tour, indoors and seated: Capital One Hall has the Main Theater, with The Steepwater Band opening. Parking isn't included or attached — it's the garage on Capital One Drive South, and the walk is outside. Buy the pass with the ticket.
Sat 9/5, 7:30 p.m., doors 6:30 · $54–$101, fees in, before tax · ~30 min, 7750 Capital One Tower Rd, Tysons · Adults
Oysters and a pumpkin ale release at Dirt Farm on Sunday: the brewery puts out its pumpkin ale, brewed with neck pumpkins grown on the farm, alongside raw and charbroiled Nomini Bay oysters. The taproom and patio run 11 to 7 on Sundays. No admission is posted, so you pay for what you eat and drink.
Sun 9/6, 11 a.m.–7 p.m. · No admission posted · ~40 min, Dirt Farm Brewing, Bluemont · All ages
LoCo Fest is Sunday, and the cheaper ticket stops Saturday: 868 Estate Vineyards runs its ninth: fifteen bands, noon to nine, rain or shine. Advance tickets are $39 and stop on the 5th, then it's $50 at the gate. Sixteen and under free.
Sun 9/6, noon–9 p.m. · $39 advance, $50 same day; free 16 and under · ~35 min, 14001 Harpers Ferry Rd, Hillsboro · All ages
Shreya Ghoshal plays Wolf Trap on Sunday, and it's already selling out: Wolf Trap calls her one of Bollywood's music megastars, and this is the Unstoppable Tour. Gates at 6, music at 7:30, parking free with the ticket. The venue has it marked limited availability, and it doesn't print a price range on the page, so you'll see the tiers at checkout.
Sun 9/6, 7:30 p.m., gates 6 p.m. · Price shown at checkout; limited availability · ~30 min, Filene Center, 1551 Trap Rd, Vienna · Big kids and up
The 27th annual car show takes over downtown Fairfax on Labor Day, and it's free: the City of Fairfax runs it with the Clifton Lions Club, 8 to 2 on University Drive. Free to walk in, with a nominal donation encouraged; all of it goes to Life with Cancer and the Cloverleaf Equine Center. Six hours wide, so a slow start still works.
Mon 9/7, 8 a.m.–2 p.m. · Free, donations encouraged · ~40 min, 4081 University Dr, Fairfax · All ages
The 88th Gaithersburg parade is worth the drive, but park before you commit: the city starts it at 10 in Olde Towne on a new route this year, up Russell Avenue and along East Diamond. Marching bands, antique cars, fire engines, horses. Food and activities run to 12:30. Read this part twice: there is no shuttle and no designated parking for anyone not marching. Limited free spaces sit in the Olde Towne garage at South Summit.
Mon 9/7, 10 a.m., food to 12:30 · Free · ~45 min, Olde Towne, Gaithersburg MD · All ages
Live music at Breaux on Labor Day afternoon, with food on site: Breaux Vineyards has Wayne Snow playing 2 to 5 on the holiday, and its Wieners and Wine weekend runs Monday too, so there is food on site. The tasting room is open 11 to 6. No cover is posted, so it costs whatever you drink.
Mon 9/7, 2–5 p.m. · No cover posted · ~35 min, 36888 Breaux Vineyards Ln, Purcellville · Adults
Family Fest takes the Village at Leesburg on Saturday afternoon: The Family One runs it with the shopping center. Admission and parking are free, and they ask for an RSVP anyway. The low-commitment option if you don't want a drive or a ticket.
Sat 9/5, noon–4 p.m. · Free, RSVP encouraged · ~25 min, 1602 Village Market Blvd SE, Leesburg · All ages
Hook, with the National Symphony playing the score live: Wolf Trap screens the 1991 film with the orchestra under it, Emil de Cou conducting. Parking is free. Before you budget: everyone needs a ticket regardless of age, babies included, and children pay adult prices — so a family of four on the lawn is $161.
Sat 9/5, 7:30 p.m., gates 6 p.m. · Lawn $40.25, seats $54.50–$75, fees included · ~30 min, Filene Center, 1551 Trap Rd, Vienna · Big kids and up
CatVideoFest, with adoptable cats in the lobby: the Humane Society of Loudoun County brings cats to the Alamo Drafthouse foyer from noon to 2, alongside three screenings of the touring reel. The 1:30 show lines up with meeting them.
Sat 9/5, shows 11 a.m., 1:30 and 4 p.m.; cats noon–2 · Alamo doesn't post a price before you pick seats · In Ashburn, 20575 Easthampton Plaza · Big kids and up
Wildfest is a full day outdoors at a nursery in Berryville: Loudoun Wildlife Conservancy runs it with the Blue Ridge Wildlife Center. Check before you set off: the venue is Seven Bends
Nursery in Clarke County, not Seven Bends State Park, which is a different place further west.
Sat 9/5, 9 a.m.–4:30 p.m. · No price posted · ~40 min, 76 Moose Rd, Berryville · All ages
Monday is Volcano Island's last day of the year, and it's the closest thing on this list: NOVA Parks runs the Algonkian waterpark 11 to 6, and the published 2026 schedule ends that day. It's $16 at 48 inches and taller, $12 under that and for anyone 60 and over, free under 2. Tickets are sold on-site only, on the day, so there's nothing to book ahead.
Mon 9/7, 11 a.m.–6 p.m. · $16, $12 under 48" and 60+ · ~15 min, 47001 Fairway Dr, Sterling · All ages
Great Country Farms is open all day Monday, holiday included: the farm runs 9 to 5 every day in September. Adults are $13, ages 3 to 17 and anyone 55 and over $11, under 3 free. Military families get in free Monday through Friday in September, up to six with ID. Apple picking is while supplies last and isn't guaranteed, so go for the corn maze, the play area and the market. Rain or shine.
Mon 9/7, 9 a.m.–5 p.m. · $13 adults, $11 ages 3–17 and 55+ · ~35 min, 34355 Snickersville Tpk, Bluemont · All ages
Kids Fest fills the Segra Field lots on Labor Day: the county sets up a petting zoo, bounce houses, an obstacle course, a foam zone, a toddler zone, face painting and touch-a-truck. The county calls it free, with food for sale, and says the line-up can change.
Mon 9/7, 11 a.m.–3 p.m. · Free, food for purchase · ~20 min, Segra Field lots, 42095 Loudoun United Dr, Leesburg · Little kids
Two county outdoor pools close for the season Monday, and the rec centers run 11 to 6: the county opens Ashburn, Claude Moore and Dulles South 11 to 6, pools going until 5:45, no Kid Kare. The Lovettsville and Franklin Park outdoor pools run 11 to 6:30 and shut for the season that evening. Community centers, senior centers, the Round Hill aquatic center and Franklin Park Arts Center are closed all day. Parks keep normal hours, and there's no county transit.
Mon 9/7 · Free and paid, by facility · Countywide · All ages
One Ashburn Village pool closes Monday, the others get two more weekends: the association closes only the Sports Pavilion outdoor pool for the season. Lakes and Woods stay open the weekends of the 12th–13th and 19th–20th, 11 to 8. Broadlands, separately, shuts its pools after Labor Day.
Mon 9/7 onward · Included with membership · In Ashburn · All ages
The Route 690 bridge starts coming down September 8: the county begins a phased demolition and rebuild of the bridge over Route 7. The first phase runs two to three weeks and narrows lanes to about eleven feet; the bridge stays open. It's the Purcellville interchange, so it matters if you drive west on weekends. Completion is estimated for winter 2029.
Work begins Tue 9/8 · No cost · ~30 min west, Route 7 at Route 690, Purcellville · Adults
The School Board meets Tuesday in Ashburn at 4:30: the board's document portal carries the agenda, which posts a few days ahead. Second-Tuesday meeting, the first of the school year. Registering to speak has its own deadline.
Tue 9/8, 4:30 p.m. · Free · In Ashburn, 21000 Education Ct · Adults
Fall Ultimate signups close today, and the fields are in Fairfax: FXA shuts signups for all three fall leagues on the 2nd. Games run 8 to 10 p.m. Start dates differ: Sunday the 13th, Wednesday the 16th, Thursday the 17th. Individual signup is $45 and a team is $525, though those numbers sit in the league listing, not on the page linked here. Every field is in Fairfax County.
Closes today, Wed 9/2 · $45 solo, $525 a team · ~30 min, Fairfax County turf · Adults
Ashburn Youth Basketball closes Monday, and the fee is now $265: the league shuts registration on the 7th and says plainly that no late ones will be considered. From September 1 to 7 the fee is $265, including the $25 fundraising fee. The league's own home page still shows the earlier $240. Grades 3 through 12, first come, first served.
Closes Mon 9/7 · $265, including the $25 fundraising fee · In Ashburn · Grades 3–12
Two dog swims, same Saturday, both pre-registration only: Broadlands runs its
Pooch Pool Party at Summerbrooke in fifty-minute slots from 9 to 1, $7 a dog a slot, no refunds, waiver and rabies certificate required. South Riding runs
its own at the Town Hall pool noon to 3, $15, South Riding residents only. Two separate events, and neither takes walk-ins.
Sat 9/12 · $7 a dog a slot; $15 · In Ashburn area · All ages
Bluemont Fair, September 19 and 20: the fair has run since 1970 and is put on entirely by volunteers. Ten to five both days, $10 at the gate in cash or card, free for ages 9 and under, parking free. No pets on the grounds.
Sat 9/19 and Sun 9/20, 10 a.m.–5 p.m. · $10 at the gate, free 9 and under · ~35 min, 33846 Snickersville Tpk, Bluemont · All ages
Cox Farms opens September 19, and tickets are online only: the farm needs a ticket for everyone 2 and up and says busy dates sell out, which is why this is here three weeks early. The Fall Festival runs to November 8, 10 to 6 through October. Pricing is tiered by date and opening weekend is the $25 tier.
Opens Sat 9/19, runs to Nov 8 · $25 opening weekend, tiered by date · ~35 min, 15621 Braddock Rd, Centreville · All ages
The Leesburg Airshow is September 26, and you park somewhere else: the Town runs it 11 to 4 at the Executive Airport. Entry is free and so are the shuttles. There's no parking at the airport beyond limited accessible spaces — park at Heritage High School or Segra Field and ride in.
Sat 9/26, 11 a.m.–4 p.m. · Free · ~25 min, Leesburg Executive Airport · All ages
The data center rewrite comes to Broad Run High on September 28: the county holds a drop-in session in the cafeteria. No presentation, no set start: you turn up and talk to planning staff. An identical session runs the 30th in Leesburg. What people say feeds a Planning Commission review expected in February 2027.
Mon 9/28, 6–8:30 p.m. · Free · In Ashburn, 21670 Ashburn Rd · Adults
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