A downtown Friday, a split Saturday, and a clean Sunday run.
This weekend gives you a real choice instead of one obvious anchor: Leesburg First Friday to ease in, a family-heavy Saturday split between Sterling and Leesburg, a more focused wine-country tasting at 8 Chains, and Run the Greenway if you want Sunday to start with movement.
Last checked Thursday, April 30, 2026. Times, tickets, and event details can change, so verify before you go.
Planning Note
Saturday is the decision point. Spring Fest, Loudoun Latino Festival, Pet Festival, Loudoun Pours, Annie, and a Tally Ho show all overlap enough that you should pick a lane before leaving home instead of trying to bounce between everything.
Quick Read
Friday: Use Leesburg First Friday if you want flexibility, or Zoso at Tally Ho if you want one ticketed room.
Family Saturday: Spring Fest is the clean morning/early afternoon pick.
Community Saturday: Loudoun Latino Festival is the broadest free afternoon block.
Wine country: Loudoun Pours at 8 Chains is the focused adult tasting.
Sunday reset: Run the Greenway early, then Annie if you want a calmer finish.
Friday Night
Leesburg First Friday
Friday, May 1, mostly 6:00 PM to 9:00 PM
Historic Downtown Leesburg
The easiest Friday move because it does not need a single fixed plan. Use the official schedule to string together a few open houses, live music stops, tastings, and downtown businesses instead of committing the whole night to one room.
Downtown businesses set their own windows; check the official schedule before you walk. Official details
Zoso - The Ultimate Led Zeppelin Experience
Friday, May 1 at 7:00 PM
Tally Ho Theater, Leesburg
The loud Friday alternative to the downtown stroll. If First Friday feels too scattered, this gives you one ticketed room, one start time, and a familiar Zeppelin tribute lane.
Ticketed indoor show. Official details
Saturday Daytime
Spring Fest
Saturday, May 2 from 10:00 AM to 2:00 PM
Loudoun Heritage Farm Museum at Claude Moore Park, Sterling
The strongest early Saturday family pick. It is free, county-run, and built for wandering: moon bounces, spring crafts, temporary tattoos, live animals, education stations, food trucks, and free museum admission.
Free event. Rain or shine. Official details
Loudoun Latino Festival
Saturday, May 2 from 12:00 PM to 5:00 PM
Douglass Community Center, Leesburg
The broadest community festival of the weekend. Expect live music, cultural performances, food vendors, local organizations, shopping, and plenty for kids, including face painting, crafts, moon bounces, and giveaways.
Free event. No registration required. Official details
Leesburg Pet Festival
Saturday, May 2 from 1:00 PM to 5:00 PM
Village at Leesburg, Leesburg
A useful add-on for animal people and families already near Leesburg. Expect pet exhibitors, rescue adoptions, a lure course, face painters, caricatures, and the Leesburg's Got Talent Pet Edition stage block.
Pet-friendly and family-friendly. Official details
Saturday Evening
Loudoun Pours to Explore
Saturday, May 2 from 6:00 PM to 8:00 PM
8 Chains North Winery, Waterford
The adult wine-country pick of the weekend: a two-hour, walk-around tasting from the Loudoun Wineries and Winegrowers Association, focused on Viognier and Bordeaux-style wines from local producers.
Ticketed through Eventbrite: $65 ticket plus $6.21 fee, $71.21 total. Official details
Goose Creek Players: Annie
Saturday, May 2 at 2:00 PM and 7:30 PM
Franklin Park Arts Center, Purcellville
The indoor family lane if Saturday weather or crowds get annoying. This is the closing weekend, so it also works as a Sunday matinee if you want the weekend to end calmly.
$25 general admission. Official details
Sunday
Run The Greenway
Sunday, May 3. 5K and 5K Roll at 8:00 AM; 10K at 8:10 AM; Kids Fun Run at 10:00 AM
Loudoun Station, Ashburn
The clean Sunday reset and one of the more unusual local races: a chance to run, walk, or roll on the Dulles Greenway while supporting local nonprofits. It gives the weekend a clear finish instead of another festival decision.
Race-day packet pickup starts at 6:30 AM. Saturday packet pickup and the Wellness Expo run 10:00 AM to 4:00 PM at Lightridge High School. Official details
Goose Creek Players: Annie
Sunday, May 3 at 2:00 PM
Franklin Park Arts Center, Purcellville
A useful final matinee if you want the weekend to end indoors and close to home.
If someone in Loudoun is trying to choose between too many Saturday options, send this to them.
Late add: Derby Days at Breaux Vineyards in Purcellville (Paid)
Saturday, May 2 at 11:00 AM. Kentucky Derby viewing party with hat contests, food, and live music. Kids and dogs are welcome on the patios and lawns.
Official details: Breaux Vineyards events page.