Use Friday's warmth. Keep Sunday flexible.

Friday, October 2 through Sunday, October 4 from 10:00 AM to 5:00 PM daily Historic Waterford village

The village becomes a walkable fairground for three days, with juried craft artisans, traditional demonstrations, historic home tours, living history, music, food, and children's activities. This is the weekend's biggest distinctly Loudoun event, and the new all-weekend pass makes a short Friday visit plus a return trip possible.

Adult all-weekend passes are $20 in advance or $25 at the gate. Seniors, military members, and guests ages 13 to 21 pay $20. Children 12 and under are free with a paid adult. Parking is free, and the fair notes that there are no ATMs on site.

Friday, October 2; doors open at 6:30 PM Tally Ho Theater, 19 West Market Street, Leesburg

The DC Improv brings five comics to Tally Ho for the clearest adults-first plan of the weekend. It is also the easiest way to keep Friday going after an afternoon at Waterford without gambling on late-night outdoor weather.

Tickets are required. The lineup includes Haywood Turnipseed, Amber Hendrix, D Lo, Bill Monaghan, and host Nelson Fuentes.

Saturday, October 3 from 12:00 PM to 5:00 PM Historic Douglass High School Education and Development Campus, 407 East Market Street, Leesburg

This free celebration pairs the history of Loudoun's first and only Black high school with hands-on activities, live entertainment, a historical scavenger hunt, mini golf, moon bounces, food, and more than 50 community vendors. It works as both a family outing and a meaningful local history stop.

The event runs rain or shine. Parking is available at Frederick Douglass Elementary, with free parking and shuttle service from the Leesburg Park and Ride at 19730 Sycolin Road.

Friday, October 2 through Sunday, October 4 from 9:30 AM to 6:00 PM Leesburg Animal Park, 19246 James Monroe Highway, Leesburg

Pumpkin Village combines the animal park with giant hill slides, moon bounces, wagon rides, pedal carts, a corn bin, and weekend entertainment. Pick this when the kids need several hours of activity and a single admission that covers both the festival and the animals.

Friday admission is $18.95 per person. Saturday and Sunday admission is $24.95 per person, and weekend tickets must be purchased online. Children under age 2 are free.

Sunday, October 4 from 12:00 PM to 4:00 PM Ashburn Volunteer Fire and Rescue Station 6, 43765 Ashburn Volunteer Plaza, Ashburn

Station 6 opens for apparatus displays, station tours, equipment demonstrations, fire and life safety lessons, and time with local firefighters, EMTs, and volunteers. It is a practical Sunday choice for younger kids who want to see the trucks up close.

Park at the elementary school at 43700 Tolamac Drive, then use the shuttle to the station. The official page lists free hot dogs and an ice cream vendor. Check for weather updates before leaving.