Saturday has the biggest choices. Keep an indoor backup.
Loudoun Loop is the 5 best things to do in Loudoun this weekend, sent every Thursday morning.
The last full weekend before Labor Day has a good split: carnival rides and heavy equipment for families, a focused Loudoun wine tasting, and three very different Saturday-night concerts. Friday night and Saturday carry the highest storm chances, so use the earlier outdoor hours and keep Tally Ho ready if the weather turns.
Weather note: Last checked Thursday, August 20, 2026. The National Weather Service point forecast for Leesburg called for a high near 79 on Friday with a 20 percent daytime rain chance, followed by a 70 percent chance Friday night. Saturday had a 70 percent chance of showers and thunderstorms, with a high near 82. Sunday looked better, with a high near 82 and a 20 percent chance after 2:00 PM. Check outdoor event status before leaving.
Read on the web: https://loudounloop.com/issues/august-21-23-2026/
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One Loudoun Carnival at Uptown
Friday, August 21 from 5:00 PM to 11:00 PM; Saturday from 1:00 PM to 11:00 PM; Sunday from 3:00 PM to 11:00 PM
One Loudoun Uptown, 44578 Atwater Drive, Ashburn
Official event page: https://www.downtownoneloudoun.com/events/one-loudoun-carnival-at-uptown-august-2026-7befl
The easiest flexible family plan, and this is the carnival's final weekend. Friday adds free Summer Strings from 6:00 PM to 9:00 PM. Saturday adds a free country concert from 7:00 PM to 9:00 PM, so you can build dinner, music, and rides into one stop.
Good to know: Admission is free. Ride tickets and wristbands cost extra and can be purchased on site or through the official page. Outdoor music may change with the weather.
Top Gun Construction Rodeo
Saturday, August 22 and Sunday, August 23 from 9:00 AM to 5:00 PM
Great Country Farms, Bluemont
Official event page: https://greatcountryfarms.com/top_gun_construction-rodeo/
The best family pick for anyone who likes big machines. Skilled operators compete in heavy-equipment challenges, while families can get close to the equipment and use the farm's play area, wagon rides, animals, and other regular attractions.
Good to know: Advance one-day tickets are $12 per child and $14 per adult, plus a $1 ticketing fee. Two-day tickets are $20 per child and $25 per adult. Gate admission is $16 per guest age 2 and older. Bring hearing protection for little ears.
Loudoun Pours to Explore
Saturday, August 22 from 6:00 PM to 8:00 PM
Walsh Family Wine, Purcellville
Official event page: https://www.loudounwine.org/pours-to-explore
The adult pick for people who want to learn something while they taste. More than a dozen Loudoun wineries are pouring sparkling wines, Chardonnay, and Tannat, with a sommelier available to explain the styles and answer questions.
Good to know: Tickets are $65 per person. Light bites are included, and additional wine is available for purchase. Tickets were still available through the organizer's official page when checked Thursday morning.
Tarara Summer Concert Series: E5C4P3
Saturday, August 22; gates at 5:00 PM, concert from 6:00 PM to 9:30 PM
Shadow Lake at Tarara, Leesburg
Official event page: https://www.tararaconcerts.com/schedule
The large outdoor music choice is a full evening of Journey songs. Take chairs or a blanket and a picnic, then watch the weather because Saturday has the weekend's highest daytime storm chance.
Good to know: Concerts are rain or shine unless lightning forces a delay or cancellation. Online general admission is $20 for guests 21 and older and $10 for guests under 21, plus fees and tax. Door admission is $25 for guests 21 and older and $10 for guests under 21. Guests under 10 are free.
Tally Ho Theater weekend shows
Friday, August 21 or Saturday, August 22; doors at 7:00 PM
Tally Ho Theater, Leesburg
Official venue page: https://tallyhotheater.com/
The reliable indoor option when the radar looks bad. Friday is Nirvani, a Nirvana tribute. Saturday is So Fetch, a 2000s dance party that runs from Avril Lavigne and Blink-182 to Outkast and Beyoncé.
Good to know: Both shows are ticketed and still showed ticket links on the official venue site Thursday morning. Check current prices and availability before leaving.
ALSO WORTH KNOWING
Dirt Farm Peak Season Supper Club
Friday, August 21 from 7:00 PM to 9:00 PM
Dirt Farm Brewing, Bluemont
Official event page: https://dirtfarmbrewing.com/event/supper-club-peak-season-august-21-2026/
A four-course, 21-and-older dinner with beer pairings, including corn tamales, chilled avocado soup, smoked brisket, and chocolate blackberry pudding. It is outside by default, but the brewery says it will move indoors or under the pavilion for bad weather.
Good to know: $110 per person for nonmembers and $100 for CSB members, including fees and gratuity. Reservations are required, and tickets are nonrefundable.
Leesburg Summer JAMS: Levi Stephens
Saturday, August 22 from 7:00 PM to 8:30 PM
Leesburg Town Green, 25 West Market Street
Official event page: https://www.leesburgva.gov/departments/parks-recreation/events/summer-jams
The free downtown choice and the final Summer JAMS concert of the season. Stephens mixes soul, R&B, rock, and folk, and the early finish leaves time for dessert or a drink downtown.
Good to know: Free and open to the public. Bring a chair or blanket. The Town cancels for bad weather and posts updates on the event page and Ida Lee's Facebook page.
Bikes, Brews and Views with Fast Eddie
Sunday, August 23; motorcycle meet-up from 12:00 PM to 6:00 PM, live music from 1:00 PM to 4:00 PM
Dirt Farm Brewing, Bluemont
Official event page: https://dirtfarmbrewing.com/events/month/
A specific but easy Sunday plan for riders and friends who like motorcycles, mountain views, beer, and live music. The brewery's weekend lobster rolls are also available while supplies last.
Good to know: The meet-up and music have no listed cover. Food and drinks are sold separately. Sunday hours are 11:00 AM to 7:00 PM.
Forward this to one Loudoun friend who is still deciding what to do this weekend. New readers can join free at https://loudounloop.com/#signup.
Read on the web: https://loudounloop.com/issues/august-21-23-2026/