Things to Do

Why Singer Tracy Hamlin Loves Leesburg

"I love the quaintness of the historic district."

Tracy Hamlin at a concert over the summer. Photograph Courtesy of DMH Records/

Jazz and R&B singer Tracy Hamlin has performed alongside Carlos Santana and Chaka Khan, toured internationally as a background vocalist for Gloria Gaynor, and released five solo albums. In the Loudoun County resident’s most recent act, she brought the Sweet Jazz & Wine Festival to Leesburg at Tarara Winery in October.

Why pick Leesburg for your festival?

Jazz lovers in Loudoun County have to go to DC or Baltimore to find good music. Tarara Winery has a stage suited to Grammy-winning artists. The backdrop of the stage is a lake. People bring chairs, eat good food, drink good wine, and listen to good music. This is the first year of what we hope will be an annual event.

I had been organizing this jazz-and-music party for about 200 people on Saint Lucia each year for a music lover and millionaire. It was an annual two-day party, where I performed and brought in other award-winning artists like Marcus Miller, Sheila E., and Kevin Eubanks. By year two, I was organizing the whole event—booking artists, menu, and travel. This festival grew from there.

What about Leesburg do you love?

I love that it’s so diverse. It’s where I go to shop. I love Leesburg Corner Premium Outlets; I love the designers like Kate Spade—God bless her soul. I’ve performed in 56 countries and am constantly traveling the world. I’m always mixing and matching my wardrobe, but I’m always looking for unique things to wear onstage. I can get the cutest things in Leesburg.

What are your favorite haunts?

I love spending time in the historic district. It’s so quaint. I like to go to Shoe’s Cup & Cork for a coffee or breakfast. The first time we went out to the patio in the back, my husband and I were shocked and thrilled that they had a bocce pit. My husband keeps a bocce set in his car, and it’s the highlight of family gatherings. We played that day at Shoe’s for hours.

How did you get into singing?

I started when I was five. My brothers used to sing in the house and for family, imitating the Temptations, and at first I used to fill in for them from time to time. But soon I wanted my own solo act.

I went to the Baltimore School for the Arts and to Peabody Preparatory school of music. When I was 11, I auditioned for an R&B band called Fragile Glass, and they hired me as a featured guest. My brother made me a gown, and I’ve been performing live ever since. As I got older, I did a lot of private events. When I couldn’t get a record deal, I started my own label, called DMH Records, named after my mother.

Who’s your favorite singer to work with?

Wynonna Judd blew my mind. I worked with her in 2017 at the Grammys on the Hill event, where singers perform for Congress. When I work with other artists, I’m like a sponge. Wynonna is so warm and fuzzy, and not intoxicated with her fame.

What are the biggest changes you’ve seen in Leesburg over the past few years?

The area is expanding so much. I love the quaintness of the historic district—it’s so unique, especially since the surrounding areas are developing so much. Even in Leesburg’s outskirts, there’s a lot of construction. I hope we can keep the intimacy of the historic district.

This article appears in the October 2018 issue of Washingtonian.

Grace Cutler

Grace Cutler is a media consultant and digital-video executive. In 2014, she contracted a tick-borne illness while working in her garden in western Loudoun County, forcing her to change the way she eats and drinks and how she thinks about the outdoors. On Twitter, she’s @gcutler.