A real Saturday slate, then a Sunday that needs a lane.
Saturday is not quiet: Art in the Burg, the PRCS Food Truck Festival, Frozen, dinner theater at Casanel, and an ABBA tribute at Tally Ho all stack up. Sunday is the Mother's Day decision: farm breakfast, brunch boards, a 5K, flowers, or a mountain brunch.
Last checked Friday, May 8, 2026. Times, tickets, sellouts, and event details can change, so verify before you go.
Planning Note
Do not treat Sunday as one generic brunch slot. The stronger play is to choose the kind of Mother's Day you want before you leave: kid-forward at Henway and Great Country Farms, winery brunch at 8 Chains, a 21-and-older wine bar meal at Echelon, or the active route with Mom's Day 5K.
Quick Read
Strongest Saturday: Art in the Burg in Middleburg, 11:00 AM to 6:00 PM.
Best family Saturday: PRCS Food Truck Festival at Segra Field, 11:00 AM to 3:00 PM.
Date night: Hopelessly Devoted to Murder dinner theater at Casanel, Saturday evening.
Best Mother's Day with kids: Moms and Muffins at Henway Hard Cider and Great Country Farms.
Winery brunch: 8 Chains North brunch boards and bubbly bar.
In-town grown-up option: Echelon Wine Bar for a 21-and-older Mother's Day brunch.
Saturday Daytime
Art in the Burg
Saturday, May 9 from 11:00 AM to 6:00 PM
South Madison Street and Federal Street, Middleburg
The strongest Saturday pick. Middleburg turns into a walkable arts day with local and regional artists, music, performances, food, wine, beer, cider, and free kids activities. The VMFA Artmobile is also in town at Middleburg Community Charter School with its Virginia as America exhibition.
Free to attend. Expect road closures and parking pressure in downtown Middleburg. Official details
PRCS Food Truck Festival
Saturday, May 9 from 11:00 AM to 3:00 PM
Segra Field parking lot, Leesburg
The broadest family-friendly Saturday option if you want food, activity, and very little planning. Loudoun PRCS lists more than 15 food vendors, live music, retail vendors, axe throwing, splatter paint, a rage room, games, and scavenger hunting.
Free admission, rain or shine. Food and drinks are sold by vendors; outside food and drink are not allowed except capped clear water bottles. Official details
Pickwick Players: Disney's Frozen
Friday, May 8 at 7:30 PM; Saturday, May 9 at 1:00 PM and 7:30 PM
Capital Community Church, Ashburn
The indoor family lane and a useful backup if weather, pollen, or Saturday crowds make outdoor plans feel like too much. Pickwick is staging Frozen's Broadway version with a local community cast.
Advance tickets are listed at $21 for adults and $16 for students or seniors, with higher pricing at the door. Official details
Saturday Night
Hopelessly Devoted to Murder at Casanel Vineyards
Saturday, May 9. Doors and dinner at 6:30 PM, show at 7:15 PM
Casanel Vineyards and Winery, Leesburg
The Saturday-night date pick: a 1950s murder mystery dinner theater at a Leesburg winery. It is the best full-evening plan because dinner, dessert, show, and setting are already bundled.
Tickets are $77 plus sales tax and ticketing fee; Casanel Wine Club members have a discounted option. Official details
Tally Ho tribute weekend
Friday, May 8 at 7:00 PM; Saturday, May 9 at 7:00 PM
Tally Ho Theater, Leesburg
The concert lane splits cleanly: Haus of Monsters brings the Lady Gaga tribute Friday, then Mamma Mania brings ABBA on Saturday. If you are choosing just one, Saturday's ABBA show fits the Mother's Day weekend mood better.
Both are ticketed indoor shows. Saturday's Mamma Mania listing starts at $37.67 before fees. Official details
Sunday
Moms and Muffins at Henway Hard Cider
Sunday, May 10. Breakfast seatings at 9:00 AM, 9:30 AM, and 10:00 AM
Henway Hard Cider at Great Country Farms, Bluemont
The best kid-forward Mother's Day plan I found. Breakfast includes muffins, fruit, coffee, juice, Great Country Farms admission, and a Mom and Me craft station, with cider-mosas for adults and farm fun wrapped into the morning.
Reservations required. Pick one of the morning breakfast seatings before you go. Official details
Mother's Day Brunch Boards and Bubbly Bar
Sunday, May 10 from 10:30 AM to 1:00 PM
8 Chains North Winery, Waterford
The cleanest winery brunch alternative if you want food and bubbles without the big-hotel brunch format. Brunch boards feed two adults and include breakfast and lunch bites like egg bites, waffles and chicken, croissants, fruit, yogurt, charcuterie, and macarons.
Pre-order boards through Eventbrite. Mimosas are available separately at the bubbly bar. Official details
Mom's Day 5K
Sunday, May 10 at 9:00 AM
Philip A. Bolen Memorial Park, Leesburg
The active Mother's Day option if you want Sunday to start before brunch. All ages and paces are welcome, and registered participants get a commemorative shirt and finisher medal while supplies last.
Registration is $35 through Loudoun County PRCS. Check availability before you drive. Official details
Mother's Day Brunch Buffet and Bouquets at Dirt Farm
Sunday, May 10 from 11:00 AM to 1:00 PM
Dirt Farm Brewing, Bluemont
The beer-and-mountain-view brunch option. The buffet includes a Mother's Day spread, Fleur De Leah bouquets are available by pre-order, and Dirt Farm opens outdoor areas for non-brunch guests later in the day.
$57 per adult and $30 for children 10 and under. Reservations required for brunch. Official details
Mother's Day Celebration at Echelon Wine Bar
Sunday, May 10 from 10:00 AM to 2:00 PM
Echelon Wine Bar, Leesburg
The best in-town grown-up backup if winery brunches are booked. Echelon is running a Mother's Day brunch with seasonal dishes and sparkling sips in downtown Leesburg.
21 and older only. Make a reservation and check the brunch menu before you go. Official details
If someone in Loudoun is still trying to choose a Mother's Day weekend lane, send this to them.