October in Leesburg is a season of crisp air, colorful leaves, and a calendar full of Halloween excitement. From historic ghost tours to family-friendly festivals, our town transforms into a hub of spooky fun, festive activities, and long-standing traditions. No matter your age or interests, there’s something to make this Halloween season memorable.
Haunted History Comes Alive
For those who love a little thrill with their history, the Loudoun Museum’s Hauntings offers an unforgettable evening. Since 1991, volunteers have guided visitors through downtown Leesburg on 80-minute walking tours, sharing chilling tales of lingering spirits, deadly duels, and poisoned plots. Stops this year include the Historic Charles Hamilton Houston Courthouse, Presbyterian Church, St. James Episcopal Cemetery, and the Johnston House, each brimming with stories of the past. As one of the museum’s largest fundraisers, Hauntings also supports exhibitions, educational programs, and community events, making it a truly enriching—and eerie—experience.
A Night on Wheels
Not all thrills need to be spine-tingling. For those looking for playful fun, Spooky Skate Night at Douglass Community Center is the place to be. On Friday, October 24, from 6–9 p.m., skaters can glide beneath glowing lights to festive tunes, enjoy treats, and even hop aboard the haunted train for a unique twist on a night out. With affordable admission and skate rentals available on site, it’s a fun way for families and friends to get moving and celebrate the season together.
Family Fun & Safety
The following afternoon, Leesburg continues its Halloween festivities at Village at Leesburg. From 1–5 p.m. on Saturday, October 25, Monster Mash invites kids and families to enjoy pumpkin carving, trick-or-treating, cookie decorating, face painting, and a costume contest. Children, families, and even pets can show off their best Halloween looks on the Main Stage from 3:30–4:30 p.m.
At the same time, the Loudoun County Sheriff’s Office hosts Child Safety Day, offering demonstrations of public safety equipment, K-9 unit displays, and women’s self-defense presentations. Kids can even add their hand-print to an LCSO cruiser, creating a fun and interactive experience that emphasizes safety while celebrating the season.
A Beloved Tradition
No Halloween in Leesburg would be complete without the town’s signature parade. The Kiwanis Club of Leesburg has proudly organized the country’s longest-running Halloween parade since 1957, and this year marks a special change: for the first time, the parade will take place on Thursday, October 30, at 6 p.m., giving families the chance to enjoy both the parade and Halloween trick-or-treating.
The parade begins at Ida Lee Park and winds through Historic Downtown Leesburg, featuring floats, marching bands, community groups, and plenty of candy for kids of all ages. Decorated floats will be judged in three categories: Best Float, Most Creative, and Best Interpretation of the Halloween Theme. Participation is free, and attendees are encouraged to bring food donations for Loudoun Hunger Relief, supporting children and families throughout the county.
From ghostly tales to glow-in-the-dark skating, Leesburg offers a little something for everyone this Halloween season. Dress in your favorite costume, gather your friends and family, and explore all the tricks, treats, and traditions our town has to offer.