This is a Loudoun weekend you can actually plan around.

Friday, May 29 through Sunday, May 31; Friday opens at 4:00 PM, Saturday and Sunday open at 1:00 PM The Farm Brewery at Broad Run, 16015 John Marshall Highway, Broad Run

This is the easiest family-first pick of the weekend because it gives you rides, games, food, drinks for the adults, and enough room to make it feel like an actual night out instead of another playground stop. If Saturday is already too packed, use Friday as the cleaner move.

Cole Shows lists the carnival as running through June 7. Admission, rides, and wristbands are separate, so check pricing before you go.

Saturday, May 30; race starts at 7:00 AM, wine festival runs 9:00 AM to 12:00 PM Doukenie Winery, 14727 Mountain Road, Hillsboro

A very Loudoun way to spend Saturday morning: run through wine country, then stay for the festival at Doukenie. Even if you are not racing, this is worth knowing because it will shape traffic and energy around Hillsboro and western Loudoun.

Registration is required for races and the wine festival. If you are not participating, check access and parking details before heading that way.

Saturday, May 30 and Sunday, May 31 from 9:00 AM to 5:00 PM Great Country Farms, 18780 Foggy Bottom Road, Bluemont

The reliable farm day: wagon rides, play areas, strawberry treats, contests, and the kind of easy kid energy that does not require overthinking. It is the best choice here if you want a daytime plan that can carry a few hours.

Ticketed farm admission. U-pick and strawberry availability can change with weather and field conditions.

Saturday, May 30 and Sunday, May 31; taproom hours are 11:00 AM to 7:00 PM Dirt Farm Brewing, 18701 Foggy Bottom Road, Bluemont

If you want the weekend to feel outdoorsy without turning it into a serious expedition, this is the pick. Dirt Farm is pairing its mountain trails with vendors, guided hikes, food specials, drinks, and live bluegrass across the weekend.

The main trail is a real 3.5-mile hike with elevation, so wear shoes you can walk in.

Saturday, May 30; doors at 5:00 PM, concert from 6:00 PM to 9:30 PM Tarara Winery, 13648 Tarara Lane, Leesburg

Tarara's outdoor concert setup is still one of the cleanest Saturday night plans in Loudoun. The New Romance is an 80s tribute band, which means this is the pick if you want a big, familiar, danceable night instead of a quiet tasting.

Ticketed event. Bring the usual outdoor concert setup and check Tarara's rules before you pack.