Loudoun Loop is the 5 best things to do in Loudoun this weekend, sent every Thursday morning.

Father's Day is the useful planning filter this weekend.

This is a clean weekend if you decide what kind of plan you want. Friday is the indoor option at Tally Ho. Saturday has the strongest evening choices: free music on Town Green, Delta Spur at Tarara, or polo at Morven Park. Sunday is the Father's Day move, with fishing, bingo, cider, and farm admission at Henway and Great Country Farms.

Last checked Thursday, June 18, 2026. The NWS forecast for Leesburg showed a Friday morning shower chance, a sunny Saturday near 83, and a sunny Sunday near 87 before rain chances return Sunday night. Times, tickets, weather, and event details can change, so verify before you go.

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Best Friday indoor plan: 11 Days at Tally Ho.

Best free Saturday plan: Leesburg Summer JAMS on Town Green.

Best outdoor concert: Delta Spur at Tarara.

Best classic Loudoun night: Polo in the Park at Morven Park.

Best Father's Day plan with kids: fishing and bingo at Henway and Great Country Farms.

Best grown-up Father's Day backup: Bluemont Vineyard or Dirt Farm.

Best Saturday morning errand: Leesburg Saturday Farmers Market.

Friday, June 19; doors at 6:30 PM
Tally Ho Theater, Leesburg

This is the Friday pick if you want something indoors and more substantial than another dinner reservation. It is a ticketed documentary night tied to the Afghanistan evacuation story, so it is a better fit for adults or older teens than for a loose family outing.

Ticketed. Tally Ho listed Friday tickets as available when checked. Official details

Saturday, June 20 from 7:00 PM to 8:30 PM
Town Green, Leesburg

This is the easiest Saturday night choice because it is free, central, and simple to pair with dinner downtown. Harmony Holler brings country, rock, and singalong energy, which makes it the low-friction pick if you want music without buying a ticket.

Free. Bring a chair or blanket. Leesburg says no pets or smoking in the grass listening area, and weather can cancel the show. Official details

Saturday, June 20; gates at 5:00 PM, concert from 6:00 PM to 9:30 PM
Tarara Winery, Leesburg

Tarara is the bigger outdoor concert move this weekend, with Delta Spur giving the night a country lean. Pick this if you want to settle in for the whole evening rather than bounce between downtown stops.

Ticketed. Tarara says concerts are rain or shine, bands and food trucks can change, outside alcohol is not permitted, and all ticket sales are final. Official details

Saturday, June 20 from 6:00 PM to 10:00 PM
Morven Park International Equestrian Center, Leesburg

This is still the classic Loudoun summer-night pick. Gates open at 6:00 PM, the first match starts at 7:00 PM, and the whole thing works best as a picnic-style evening around the arena.

Ticketed. Passes range from $45 to $400 including fees. Sales are final unless the event is canceled, and pets are not permitted. Official details

Sunday, June 21 from 10:00 AM to 4:00 PM
Henway Hard Cider and Great Country Farms, Bluemont

This is the most useful Father's Day plan because it gives kids, dads, and non-fishing adults something to do in one place. The fishing contest runs around the pond, live music is on the Henway patio, bingo runs in the afternoon, and admission includes Great Country Farms for the day.

Bring your own pole and gear. Advance tickets were listed at $12 for children or seniors and $14 for adults, with day-of gate admission at $16 per guest. Children 2 and under are free. Official details

Saturday, June 20 from 11:00 AM to 8:00 PM; Sunday, June 21 from 11:00 AM to 7:00 PM
Bluemont Vineyard, Bluemont

Good grown-up Father's Day backup if your plan is food, views, and a glass of wine instead of a full event schedule.

Ribs, wine, sangria, and the BBQ menu are sold a la carte. Seating is first come, first served. Official details

Saturday, June 20 and Sunday, June 21; Sunday live music from 1:00 PM to 4:00 PM
Dirt Farm Brewing, Bluemont

Use this if you want a casual west Loudoun stop with hot dog and hamburger specials, lawn games, beer, and Junkyard Jones on Sunday.

Dirt Farm also lists lobster rolls every Friday, Saturday, and Sunday through the summer while they last. Official details

Saturday, June 20 from 8:00 AM to 12:00 PM
Virginia Village Shopping Center, Leesburg

The practical Saturday morning move if your evening is already spoken for. Go early, get local food, and leave the night open for Summer JAMS, Tarara, or polo.

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