Contributed by Visit Montgomery

In 1992, Poolesville held its first Poolesville Day. The event was a small affair, but it continued to be held each year, growing in size, number of vendors, entertainment venues, and attendees. Poolesville held parades in those days, but they were in celebration of the homecoming game. By 2004, Poolesville Day included a parade and instituted its first grand marshal. 

Now, Poolesville throws an annual shindig that welcomes more than 12,000 visitors to the Poolesville Day celebration. The Town of Poolesville in Montgomery County, Maryland, is part of what locals call “UpCounty” and showcases part of our Agricultural Reserve and MoCo history. Poolesville Day celebrates the community and takes a dedicated group of volunteers to plan and pull off this spectacular event. 

There are plenty of things to do and see at Poolesville Day including a 5K Walk-Run, Classic Car Show, EV Show, Parade, and more. 

The 5K Run-Walk hosted by the Poolesville Area Chamber of Commerce & Monocacy Lions Club starts off Poolesville Day at 8:00 a.m. with the 31st annual 5K Run/Walk. All skill levels of walkers or runners are welcome at this family-friendly race. Funds from this event are reinvested back into the community to local organizations. Previously, an average of 400 walkers and runners participated. 

The Parade starts at 10:00 a.m. Dancers, live music, tractors, local schools, and community members parade down Fisher Avenue and end up at the intersection of Fisher Avenue and Route 109. 

While exploring Poolesville Day, take a blast to the past and watch the classic, vintage muscle cars or an old-school coupe as they compete for best in show at the Classic Car Show. Or look towards the present and future with the Electric Vehicle (EV) Car Show. In 2022, the EV Car Show had over 200 EVs registered, making Poolesville Day the largest National Drive Electric Week worldwide. 

The live music and entertainment at Poolesville Day are a must-see with multiple stages showcasing multiple genres of music, bands, groups, and performers. Last year, award-winning rock band from Gaithersburg, KAROUSEL performed as well as local Poolesville talent and The Bad Influence Band! 

If you are a history buff, the Historic Medley, an organization created to preserve the heritage of Western Montgomery County, will be at John Poole House showing and displaying artifacts from the 1800s. The John Poole House is the oldest house in Poolesville, a log structure built in 1793. It served as the US Post Office’s “Poole’s Store, Maryland.” 

A variety of cuisines can be found at this one-day festival including the Steak Tacos and Chicken Trippy Fries from Trippy Tacos, the handmade Crab Cakes and Crab Mac n Cheese from Sherri’s Crab Cakes, Cinnamon Rolls and desserts from Sweet Rollers, and other vendors and restaurants across the street. 

The town additionally supports its community with this day by lining up students and organizations on Falcon Lane. Falcon Lane supports students by giving them a chance to host their own vendor booth and give attendees the chance to shop from the student-sponsored booths. There is also a dunk tank where students will raise money and raise support for the activities and clubs at their schools. 

Other fun children’s activities include a Moon bounce, pony, and train rides & fun mechanical rides. 

All the festivities and fun at Poolesville Day are located at Whalen Commons at 19701 Fisher Avenue, Poolesville, MD 20837 and along Fisher Avenue. Check out a detailed event map for 2023.