Loudoun Loop is the 5 best things to do in Loudoun this weekend, sent every Thursday morning.
This weekend has two countywide draws: the Middleburg Film Festival and the Loudoun Fall Farm Tour. Sterling adds a two-day pickle and international food festival, while Leesburg, Purcellville, and Hamilton have smaller plans that do not require a full itinerary.
Weather note: Last checked Thursday, October 15. The National Weather Service expects clouds to clear Friday with a high near 82 degrees and a chance of evening storms, then mostly sunny conditions Saturday near 54 and sunny conditions Sunday near 56.
Top Picks
Middleburg Film Festival
When: Friday, October 16 through Sunday, October 18; screenings and conversations throughout each day
Where: Salamander Middleburg, The Hill School, Middleburg Community Center, and the National Sporting Library
More than 45 films, filmmaker conversations, awards events, and a concert honoring composer Daniel Pemberton make this the county's strongest adults-first option. Choose one film or conversation that still has tickets, then leave room to walk around Middleburg between venues.
Good to know: Individual tickets are required, and some screenings are sold out. Festival shuttles connect the main venues.
Dracula's Midnight Masquerade
When: Friday and Saturday at 7:00 PM and 9:00 PM; Sunday at 7:00 PM
Where: George C. Marshall's Dodona Manor, 312 East Market Street, Leesburg
This hour-long immersive show sends the audience across the candlelit grounds of Dodona Manor instead of keeping everyone in a theater seat. It is the clear Halloween-season pick for adults and older teens who want live performance, local history, and a little movement after dark.
Good to know: Advance tickets are strongly recommended. The outdoor route includes standing, walking, stairs, darkness, fog, flashing lights, sudden noises, blood, violence, and horror themes.
Loudoun Fall Farm Tour
When: Saturday, October 17 and Sunday, October 18 from 10:00 AM to 4:00 PM
Where: 34 participating farms, vineyards, nurseries, and agricultural stops across Loudoun
This is the weekend to meet alpacas, llamas, donkeys, dairy cows, growers, beekeepers, and farm producers without turning the trip into a paid attraction. Pick two or three nearby stops from the official map and stay in one part of the county.
Good to know: The tour and farm visits are free, with charges at some stops for food, drinks, and special activities. Hogback Mountain Pony Rides is marked closed for the 2026 tour.
Fall Pickle and International Food Festival
When: Saturday, October 17 and Sunday, October 18 from 11:00 AM to 6:00 PM
Where: Crooked Run Fermentation, 22455 Davis Drive, Suite 120, Sterling
A dozen pickle vendors, nearly two dozen international food trucks, a large maker market, live music, drinks, and kids activities fill both days at Crooked Run. The mix is broad enough for a family lunch stop, but pickle fans and food-truck grazers will get the most from it.
Good to know: General admission is $5 plus the card fee at the door. Children 12 and under are free. The festival uses indoor and outdoor space and runs rain or shine.
Eat Local Read Local
When: Saturday, October 17 from 11:00 AM to 2:00 PM
Where: Cascades Library, 21030 Whitfield Place, Potomac Falls
The tenth annual festival brings local writers, artists, food vendors, and live entertainment together outside the library. It is the easiest short plan for readers and families who want something genuinely local without committing the whole day.
Good to know: The festival is free, outdoors, and scheduled rain or shine. Books and food are available for purchase.
Three More Worth Knowing
Celebrate Purcellville Fall Festival
When: Saturday, October 17 from 2:00 PM to 5:00 PM
Where: Dillon's Woods, Purcellville
Music, carnival games, face painting, food vendors, and prize drawings close the town's week-long celebration. It is free and compact enough to pair with one nearby Farm Tour stop.
Harvest Festival at Mt. Defiance
When: Saturday, October 17 from 12:00 PM to 6:00 PM
Where: Mt. Defiance Cidery and Distillery, 495 East Washington Street, Middleburg
Seasonal cocktails, local beer, live music, food, apple cider doughnuts, and family activities turn the barn into an easy post-film or post-farm stop.
Truck or Treat
When: Saturday, October 17 from 2:00 PM to 6:00 PM
Where: Loudoun Heritage Farm Museum, Sterling
Decorated trucks, hayrides, a gentle haunted house, story time, and a hay maze make this the Halloween option for younger children.
Good to know: Tickets are required. Check the museum page for current pricing and availability.
Forward this to one Loudoun friend who is still deciding what to do this weekend. New readers can join free here.