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.
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.
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.
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.
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. Lost Creek lists it at $65 per person.
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.
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.
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.
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.
Start with Spring Fest in Sterling, then decide whether Loudoun Latino Festival or the Pet Festival fits your afternoon better. Keep Annie as the weather-proof backup.
Use Leesburg First Friday for a loose Friday night, Loudoun Pours at 8 Chains for the focused Saturday pick, and Zoso if you want a louder room before the weekend gets busy.
Skip the Saturday pileup and build around Run the Greenway on Sunday morning. If you still want a seated plan, close with the Annie matinee.
Loudoun Loop works best when it is read weekly. The archive shows the pacing. The inbox version is the actual product.
