Loudoun Loop is the 5 best things to do in Loudoun this weekend, sent every Thursday morning.
This is a Loudoun weekend you can actually plan around.
The strongest choices this week are easy to sort by mood. Friday is for the Farm Brewery carnival opening or a quieter westward start. Saturday has the big stuff: the Virginia Wine Country race and festival at Doukenie, Strawberry Jubilee in Bluemont, Dirt Farm's Trail Fest, Tarara's 80s night, and a Pearl Jam tribute at Tally Ho. Sunday is better for a slower reset, with a second day at the farm or Dirt Farm, plus a free sketch afternoon at the National Sporting Library & Museum.
Last checked Thursday, May 28, 2026. Times, tickets, sellouts, weather, and event details can change, so verify before you go.
Quick Read
Best family night: The Great Farm Carnival at The Farm Brewery at Broad Run.
Best big Saturday morning: Virginia Wine Country Half Marathon, 10K, and Wine Festival.
Best farm day: Strawberry Jubilee at Great Country Farms.
Best outdoors-with-a-beer plan: Trail Fest at Dirt Farm Brewing.
Best Saturday night concert: Tarara with The New Romance.
Best indoor backups: Last Ham Standing at Franklin Park or Ten at Tally Ho.
Best calm Sunday: Sunday Sketch at NSLM.
Top Picks
The Great Farm Carnival at The Farm Brewery at Broad Run
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. Official details
Virginia Wine Country Half Marathon, 10K, and Wine Festival
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. Official details
Strawberry Jubilee at Great Country Farms
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. Official details
Trail Fest at Dirt Farm Brewing
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. Official details
Tarara Summer Concert Series: The New Romance
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. Official details
A Few More Worth Knowing
Last Ham Standing Comedy Improv
Saturday, May 30 from 8:00 PM to 10:00 PM
Franklin Park Arts Center, Purcellville
A good indoor backup if you want Saturday night to be funny, local, and easy to plan without dealing with a big concert crowd.
Ticketed. Franklin Park lists adult, senior, and student pricing. Official details
Ten: A Tribute to Pearl Jam
Saturday, May 30 at 7:00 PM
Tally Ho Theater, Leesburg
Useful if your Saturday night taste runs louder than Tarara. Tally Ho has the downtown Leesburg advantage, so dinner nearby is the easy pairing.
Ticketed. Check the ticketing page for doors and age-policy details. Official details
Volunteer Expo with Josh Kragness
Saturday, May 30 from 1:00 PM to 3:00 PM
Sterling Library, Sterling
A practical, free Saturday stop if you want to meet local volunteer groups, bring kids to a low-pressure library event, or hear live guitar without building the day around it.
Sunday Sketch with Ruthie Windsor-Mann
Sunday, May 31 from 2:00 PM to 4:00 PM
National Sporting Library & Museum, Middleburg
A quieter Sunday idea in Middleburg: a free sketching session with materials provided. Good if the weekend needs one calm, creative thing before Monday hits.
Free, but check the museum listing before you go. Official details
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