Use Friday's warmth. Keep Sunday flexible.
Loudoun Loop is the 5 best things to do in Loudoun this weekend, sent every Thursday morning.
Friday gives you the warmest and driest window for the Waterford Fair, followed by comedy downtown. Saturday cools down but still has the weekend's best cluster of family and community events. Sunday may turn wet, so the Ashburn firehouse open house and any outdoor plan deserve a same-day weather check.
Weather note: Last checked Thursday, October 1. The National Weather Service expects a mostly sunny Friday near 88 degrees, a cooler Saturday near 68 after an early shower chance, and likely rain Sunday with a high near 65.
Read on the web: https://loudounloop.com/issues/october-2-4-2026/
Top Picks
82nd Annual Waterford Fair
When: Friday, October 2 through Sunday, October 4 from 10:00 AM to 5:00 PM daily
Where: 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.
Good to know: 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.
Comedy Night in Leesburg
When: Friday, October 2; doors open at 6:30 PM
Where: 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.
Good to know: Tickets are required. The lineup includes Haywood Turnipseed, Amber Hendrix, D Lo, Bill Monaghan, and host Nelson Fuentes.
Douglass Legacy Day
When: Saturday, October 3 from 12:00 PM to 5:00 PM
Where: 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.
Good to know: 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.
Pumpkin Village Fall Fest
When: Friday, October 2 through Sunday, October 4 from 9:30 AM to 6:00 PM
Where: 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.
Good to know: 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.
Ashburn Volunteer Fire and Rescue Open House
When: Sunday, October 4 from 12:00 PM to 4:00 PM
Where: 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.
Good to know: 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.
Three More Worth Knowing
Oatlands 5K: Miles for Mammograms
When: Saturday, October 3 at 9:00 AM
Where: Oatlands, 20850 Oatlands Plantation Ln, Leesburg
Run or walk a course through the Oatlands fields and woods while supporting HealthWorks breast cancer screenings for local women who are uninsured or underinsured.
Good to know: Registration is $40 and remains online through 8:30 AM on race day. Packet pickup runs from 7:30 AM to 8:45 AM.
Nomini Bay Oyster Fest
When: Saturday, October 3 and Sunday, October 4 during regular brewery hours
Where: Dirt Farm Brewing, 18701 Foggy Bottom Road, Bluemont
Nomini Bay Oyster Ranch serves Virginia-grown oysters raw, grilled, and in specialty preparations outside on the mountain. No reservations are needed, and Sunday adds live music from Junkyard Jones from 1:00 PM to 4:00 PM.
Good to know: The oyster setup is outdoors. Check the Sunday weather before driving west.
Interfaith Blessing of the Animals
When: Sunday, October 4 from 2:00 PM to 3:00 PM
Where: National Sporting Library and Museum, 102 The Plains Road, Middleburg
Middleburg-area faith leaders welcome dogs, cats, horses, livestock, birds, fish, small pets, and even favorite stuffed animals for a community blessing on the museum campus.
Good to know: The blessing is scheduled to take place rain or shine.
Closing
Forward this to one Loudoun friend who is still deciding what to do this weekend. New readers can join free at https://loudounloop.com/#signup.
Read on the web: https://loudounloop.com/issues/october-2-4-2026/