October In Leesburg: Fall Fun, Festivals & More

Fall is officially here in Leesburg, and there’s no shortage of ways to make the most of it. From festivals and farmers markets to pumpkin patches, live music and other seasonal fun, October brings plenty of reasons to get out and enjoy what’s happening close to home.

Here are some events and activities happening in and around Leesburg this October.

Dates, hours and other event details can change. Check with organizers before heading out.

Leesburg Saturday Farmers Market

When: Saturdays, 8 a.m.-noon
Where: Virginia Village Shopping Center, 30 Catoctin Circle SE, Leesburg

Start a fall Saturday with a visit to the Leesburg Saturday Farmers Market, which operates year-round and keeps its summer hours through October. Shoppers can browse a rotating selection of local and regional vendors offering seasonal produce, meats, baked goods and other locally produced foods and products.

Pumpkin Village Fall Festival

When: Daily except Tuesdays through Nov. 8, plus Nov. 3; hours vary by day
Where: Leesburg Animal Park, 19246 James Monroe Highway, Leesburg

Spend a day enjoying classic autumn activities at the Pumpkin Village Fall Festival. The family-friendly festival features wagon rides, giant hill slides, a kiddie hay maze, moon bounces, pedal carts, animal exhibits, petting and feeding opportunities, an indoor play area and plenty of other activities. Weekends bring additional entertainment, including face painting and cider tasting. Weekend and holiday tickets must be purchased online in advance.

Hauntings 2026

When: Oct. 22-24, tour times starting 6-9 p.m.
Where: Tours begin at Loudoun Museum, 16 Loudoun St. SW, Leesburg

Discover the spookier side of local history during Hauntings 2026, Loudoun Museum's annual walking tour through historic downtown Leesburg. During the approximately 80-minute evening experience, guides and storytellers share ghostly tales connected to local buildings, cemeteries and their former inhabitants. This year's stops include the Johnston House, Leesburg Presbyterian Church, Shoes Cup and Cork, St. James Cemetery and Charles Hamilton Houston Courthouse.

Monster Mash 2026

When: Saturday, Oct. 24, 1-5 p.m.
Where: Village at Leesburg, 1602 Village Market Blvd., Leesburg

Break out the costumes for an afternoon of Halloween fun during Monster Mash 2026 at Village at Leesburg. The annual celebration includes trick-or-treating, professional pumpkin carving, cookie decorating, face painting and other activities. Kids, families and pets can also show off their Halloween looks during a costume contest scheduled for 3:30 to 4:30 p.m.

Cox Farms Fall Festival

When: Thursdays through Mondays through Nov. 8, plus Tuesday, Nov. 3; hours vary
Where: Cox Farms, 15621 Braddock Road, Centreville

For another full-scale fall outing within driving distance of Leesburg, head to the Cox Farms Fall Festival. The family-friendly festival, located about a 30-minute drive away in Centreville, packs in giant slides, hayrides, farm animals, rope swings, themed play areas, the Cornundrum cornfield adventure and live entertainment. Admission also includes a small patch pumpkin to take home. Tickets are sold online and may sell out on busy dates, so advance planning is recommended.

Looking for more things to do in Leesburg this fall? Check out the Patch events calendar for more local events and activities.

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