An illustrated Loudoun weekend scene with farms, a town street, a fair and families at dusk

What's happening this weekend

Pumpkins, pretzels, and one last fair weekend

Friday 25 SeptemberSunday 27 September

The weekend guide for families in Loudoun

Loudoun has apparently decided that pumpkins, pretzels and sensible walking shoes all belong in the same weekend.

Our take

Go big Saturday at Lovettsville Oktoberfest. Save Sunday morning for a quieter, boots-on fall at Temple Hall.

Weather Report

Clear and comfortable, with Saturday and Sunday near 73°. Friday starts gently, and rain looks unlikely.

Friday

Friday 25 September

Pumpkin Village Fall Fest

Leesburg Animal Park, Leesburg

Saturday 19 September – Sunday 8 November9:30am–5pm
TicketedUnder 5Ages 5–10

Slides, animals and rides make this best for younger children. Check the day’s gate price before leaving.

What to know before you go

Go Friday for the full festival with fewer weekend crowds. Call ahead for the gate price; it only appears at checkout.

Pick your own at Wegmeyer Farms

Wegmeyer Farms, Hamilton

Friday 25 September – Saturday 31 October
Pay by the pumpkinUnder 5Ages 5–10

They hand you clippers and a wheelbarrow and point you at the field. No festival attached, no admission gate, and small children treat it as an expedition anyway. Late afternoon is the best version, when the light goes gold and the after-school crowd has gone home for dinner.

What to know before you go

Late afternoon is the sweet spot: golden light and fewer families in the field.

Loudoun Heritage Farm Museum

Loudoun Heritage Farm Museum, Sterling

Friday 25 September9:30am–4:30pm
$5 adults · $3 ages 2–12 · free under 2Under 5Ages 5–10

Indoors, inexpensive and rarely busy on a Friday. Keep this one in your back pocket for the first bad-weather weekend.

What to know before you go

The reliable rainy-day backup: indoors, inexpensive and usually quiet on Fridays.

Saturday

Saturday 26 September

Lovettsville Oktoberfest turns 30

Downtown Lovettsville, Lovettsville

Saturday 26 September10am–5pm
Free entryEveryoneUnder 5Ages 5–10Ages 11+

Kinderfest runs all day, alongside the wiener dog races, stein hauling, more than fifty craft vendors and German food. The move back to Zoldos Square makes the footprint tighter and easier with a stroller.

What to know before you go

Do not drive into town. Park at Lovettsville Community Park and take the continuous shuttle to Kinderfest.

Pumpkin Patch Opening Weekend

Great Country Farms, Bluemont

Saturday 26 September – Sunday 27 September9am–5pm
$16 per person, under 2 freeUnder 5Ages 5–10Ages 11+

Go early. The wagon ride to the patch stops running when the field lot fills, usually by 11am. Bring a wagon of your own for the walk back with pumpkins.

What to know before you go

Last tickets sell at 4pm. Opening day will be busy, so Sunday morning is the calmer choice if your schedule allows.

Fall Pumpkin Harvest

Great Country Farms, Bluemont

Saturday 26 September – Sunday 1 November9am–5pm
From $12 advanceUnder 5Ages 5–10Ages 11+

The full-day option: play areas, a corn maze and farm activities. Advance tickets cost less than the gate.

What to know before you go

Buy in advance. A family of four saves about $12 versus the gate, and pumpkins cost extra by weight.

Leesburg Saturday Farmers Market

Leesburg Saturday Farmers Market, Leesburg

Saturday 26 September8am–12pm
Free entryEveryoneUnder 5Ages 5–10Ages 11+

A year-round market on summer hours through October. It is an easy first stop before anything else and finished by lunch.

What to know before you go

Go first thing. It makes an easy first stop and closes at noon.

Saturday Morning Story Time

Ashburn Library, Ashburn

Saturday 26 September10:30am–11:15am
FreeUnder 5

Twenty minutes of books and twenty of songs. The room holds about 30 families and there is no sign-up, so line up by 10:15 if your toddler needs a front spot.

What to know before you go

Times vary by branch. Check the library calendar before choosing where to go.

Sunday

Sunday 27 September

Temple Hall, the quiet version

Temple Hall Farm Regional Park, Leesburg

Sunday 27 September9am–5pm
$15 · free under 2Under 5Ages 5–10

Same patch as Saturday, with a calmer first hour. Empty field, cold air and pumpkin cannons still loading make Sunday morning our pick of the whole weekend.

What to know before you go

Wear boots you do not care about. It is a working field, not a lawn.

Apple picking at Crooked Run Orchard

Crooked Run Orchard, Purcellville

Sunday 27 September
Pay by what you pickEveryoneUnder 5Ages 5–10Ages 11+

A proper old orchard rather than a festival, with apples and a farm stand. It suits smaller children because there is nothing to line up for and nothing to say no to.

What to know before you go

Call before setting off. The orchard asks visitors to check picking conditions as varieties turn over.

Claude Moore Park, Sterling

Claude Moore Park, Sterling

Sunday 27 September
FreeEveryoneUnder 5Ages 5–10Ages 11+

Wooded lanes, meadows, ponds and miles of trail, with pavilions if you bring lunch. Worth it this weekend specifically because everyone else is at a pumpkin patch.

What to know before you go

Bring lunch and head for the wooded trails. Eastern Loudoun feels unusually quiet here on festival weekends.

Open Gym for Big Kids

Claude Moore Recreation Center, Sterling

Sunday 27 September1pm–3pm
$5 drop-in per childAges 5–10Ages 11+

Real basketball and climbing wall time for older kids who are bored of pumpkin season. Socks required on the wall; they sell them at the desk for $3.

What to know before you go

The useful counter-programming pick for older kids who are already done with pumpkin season.

Send this weekend to someone

Our picks as one image — press and hold it to save or send.

Book this now

The things that sell out while you are not looking.

Thursday 1 October

Winter activity registration opens

Swim schools, gymnastics and indoor soccer across eastern Loudoun open winter sign-ups at the top of the month. Saturday morning slots go first. Set the reminder now, not on the day.

Saturday morning classes go first. Set the reminder before registration opens.

Saturday 3 October

Waterford Fair

Colonial-era crafts, music and tours inside eighteenth-century homes, in a village that is a National Historic Landmark in its own right. Beautiful, and busy. Buy before the week of.

Buy before the week of. The historic village is beautiful and predictably busy.

Saturday 17 October

Loudoun Fall Farm Tour

More than thirty farms open their gates across the county. The good ones fill their parking by mid-morning. Pick three, map them, and start at nine.

Choose three farms, map the route and start at nine before parking fills.

Halloween in Loudoun, curated

The pumpkin patches, gentle daytime fun and after-dark scares actually worth doing in Loudoun County — with cost, ages and the practical details before you set out.

11 events · 3 free

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The weekend guide for families in Loudoun