Loudoun Weekend Guide: May 22-25

Memorial Day weekend needs a real plan.

The weekend is bigger than a normal Friday-to-Sunday list. Saturday is the decision point: strawberries in Bluemont, horse farms around Middleburg and Upperville, Revolutionary War history at Franklin Park, Tarara's concert opener, circus shows in Sterling, and an all-day art and music fundraiser in Hillsboro. Sunday gives you NoVA MusicFest at 868 Estate, a second day for the stable tour, and a quieter Bluemont plan. Monday is different. I did not find a confirmed public Memorial Day parade in Loudoun, but there are meaningful local ceremonies in Leesburg, Lovettsville, and Purcellville, plus the Ringing in Hope race and marketplace in Ashburn. If a parade is the priority, Falls Church is the closest confirmed one I found.

Last checked Friday, May 22, 2026. Times, tickets, sellouts, weather, and event details can change, so verify before you go.

Read the web version

Loudoun's Monday options are more ceremony than parade. Purcellville does include a procession from Town Hall to the Tear Drop and a Main Street closure from about 11:55 AM to 12:30 PM, but the town is not billing it as a parade. For an actual parade, use Falls Church, which is outside Loudoun but has a 2:00 PM parade.

Best family farm day: Strawberry Jubilee at Great Country Farms, Saturday and Sunday.

Best scenic Loudoun day: Hunt Country Stable Tour, Saturday and Sunday, 10:00 AM to 4:00 PM.

Best free family history pick: Road to Independence at Franklin Park on Saturday.

Best Saturday night plan: Tarara's summer concert opener with So Fetch.

Best Sunday music plan: NoVA MusicFest at 868 Estate Vineyards.

Best Loudoun Memorial Day ceremonies: Leesburg at 10:00 AM, Lovettsville at 11:00 AM, and Purcellville at 11:45 AM.

Best active Monday option: Ringing in Hope in Ashburn.

Closest confirmed parade: Falls Church, outside Loudoun, at 2:00 PM.

Saturday, May 23 and Sunday, May 24 from 9:00 AM to 5:00 PM
Great Country Farms, 18780 Foggy Bottom Road, Bluemont

The most straightforward family plan this weekend. Great Country Farms is celebrating strawberries with farm games, wagon rides, a strawberry float parade, a pie-eating contest, and the donut strawberry shortcake people will talk about on the drive home.

Ticketed farm admission. Strawberry supply and U-pick availability change with weather, so check before driving out. Official details

Saturday, May 23 and Sunday, May 24 from 10:00 AM to 4:00 PM
Upperville, Middleburg, and The Plains area

A self-guided look inside horse farms and equestrian properties that are not usually open to the public. This is the scenic, very-Loudoun pick if you want a countryside day built around horses, farms, and the back roads around Middleburg and Upperville.

Ticketed. It is a driving tour, so look at the map before you leave and do not try to hit every property. Official details

Saturday, May 23 from 10:00 AM to 4:00 PM
Franklin Park, Purcellville

A free VA250 event with Revolutionary War history, mounted First Dragoons demonstrations, hands-on activities, historical flags, spycraft with invisible ink, corn husk dolls, hoop and stick games, and Loudoun Heritage Farm Museum demonstrations.

Free county event. Good choice for families who want something active but not hard to plan. Official details

Saturday, May 23; gates open at 5:00 PM, music runs 6:00 PM to 9:30 PM
Tarara Winery, 13648 Tarara Lane, Leesburg

Tarara's summer concert series opens with So Fetch, a 2000s dance party built around pop and throwback singalongs. Bring a chair or blanket and make it your Saturday night plan if you want a crowd, wine, and a real start-of-summer feel.

Ticketed and rain or shine. Tarara lists higher door pricing than online pricing, so buy ahead if you are going. Official details

Sunday, May 24 from 11:30 AM to 7:30 PM
868 Estate Vineyards, 14001 Harpers Ferry Road, Hillsboro

A full Sunday music fundraiser at 868 Estate with DMV artists across blues, rock, and country. All ticket proceeds support Cancer Can Rock, which helps musicians facing cancer record in a professional studio.

Ticketed fundraiser. Plan for a full afternoon and evening, not a quick tasting stop. Official details

Friday, May 22 through Monday, May 25, with multiple weekend showtimes
Under the Big Top at Dulles Town Center, Sterling

A touring French circus with aerialists, acrobats, BMX, illusion, and family showtimes. Useful if weather gets messy or you need a Sterling option that does not depend on a vineyard or farm.

Ticketed. Official schedule lists Friday, Saturday, Sunday, and Monday showtimes for Sterling/Dulles. Official details

Friday, May 22 through Monday, May 25
Dirt Farm Brewing, Bluemont

A low-effort Bluemont add-on if you are already headed west for strawberries, Hillsboro, 868, or the stable tour. Dirt Farm is calling out summertime food specials from The Garage and daily taproom hours.

Open daily; listed hours are noon to 7:00 PM Monday-Friday and 11:00 AM to 7:00 PM Saturday-Sunday. Official details

Monday, May 25 at 10:00 AM
Loudoun County Courthouse lawn, 18 E. Market Street, Leesburg

The local Memorial Day observance, hosted by Mayor Kelly Burk, with wreath laying at several war memorials. Put this on the calendar if you want the long weekend to include the reason for the holiday.

Arrive early for downtown parking. The town lists this as an observance, not a parade. Official details

Monday, May 25 from 11:00 AM to 12:00 PM
Lovettsville Veterans Memorial, Zoldos Square

Lovettsville's annual ceremony honors military personnel lost in service to the country. It is a straightforward local remembrance option if you are in northern Loudoun.

The town lists the location as the Veterans Memorial on Zoldos Square, also known locally as the Squirkle. Official details

Monday, May 25 at 11:45 AM
Purcellville Town Hall, 221 S. Nursery Avenue

Purcellville's ceremony begins at Town Hall, then includes a procession to the Tear Drop for wreath presentations, Taps, a ceremonial rifle salute, flag raising, a moment of silence, and remarks.

Main Street is scheduled to close from about 11:55 AM to 12:30 PM. This is the closest Loudoun has to a Monday procession, but it is not listed as a parade. Official details

Monday, May 25; 10K at 8:00 AM, 5K at 8:10 AM, 1-mile fun run at 9:30 AM
Christian Fellowship Church, 44505 Atwater Drive, Ashburn

A Memorial Day race, walk, and marketplace in Ashburn. The event includes 10K, 5K, and 1-mile options, plus a marketplace with vendors, food, entertainment, and family activities.

Registration is required for the races. The event supports Boulder Crest. Official details

Monday, May 25 from 9:00 AM to 5:00 PM; parade at 2:00 PM
Falls Church, outside Loudoun County

If the goal is a real Memorial Day parade, this is the closest confirmed option I found. Falls Church has a full festival day with vendors, kids' rides, live music, a ceremony at 11:00 AM, and the parade down Park Avenue at 2:00 PM.

Outside Loudoun. Worth listing because I did not find a confirmed public Memorial Day parade inside Loudoun County. Official details

If someone in Loudoun is still trying to make Memorial Day weekend plans, especially for Monday, send this to them.