About Elaine’s Music

Elaine Penn

Elaine Penn

I grew up in a musical family and have been singing professionally for most of my life. My mother, who is an amazing singer, and my father, a soulful saxophone player, met when they were teenagers performing in a big band in Danville, Virginia. Years later, they fell in love and got married. They had 4 daughters and we always had a family band.

I’ve been writing songs since I was a teenager. My sister, Vaughan and I would sit outside as kids with our acoustic guitars writing songs about changing the world. Today, I am a singer-songwriter and performer. I have co-created 3 CD’s of original music that are a blend of country, pop and Americana, with positive and uplifting lyrics.

As a singer-songwriter, my lyrics tell the story of our our common journey through human triumphs and struggles, as well as the importance of seeing the good in the world. Whether it is through my CD’s or live performances at concerts, house parties, keynotes and retreats, I want my music to be a force for love.

I have had the honor of entertaining and inspiring audiences throughout the United States, Europe and Canada. I have performed in concert halls, coffeehouses, jazz venues, spiritual centers, nightclubs, musical theater productions, and for television and radio. I have also written and performed theme songs for television documentaries. Currently, I still perform with my family band, Penn Family Music

My mission is to use this music to help people to follow their dreams, find their passion in life, overcome their fears and transform the world. 2 of these songs (Find the Love and Everyday Amazed) and 1 music video (The Test of Time) won honorable mention at Posi-fest.

Elaine Caldwell
Unity of Raleigh, NC

“I heard Elaine Penn perform for the first time, I was several months into a separation after 29 years of marriage. I had not really cried because of my recent loss. I guess the pain was just too much. After hearing her sing at church, I went to my car and sobbed for the first time. I purchased the CD “Love is the Way.” I play this CD 3 to 4 times a day. It has been my inspiration! “




Penn Family Music

Through the years, Penn Family Music has performed at numerous venues throughout the east coast. Consisting of George Penn (saxophone,) Dixie Penn (vocalist,) Elaine (me), Vaughan, Elizabeth and Georgianna (vocalists,) and other talented musicians, we entertain audiences with jazz standards, 50’s and 60’s music; and, music from the Great American Songbook. Over the past 30 years, our family band has enjoyed great performance venues such as: Sam’s Cantebury Inn, Green’s Supper Club, The Greenbrier, Pinehurst Country Club, Hotel Roanoke, Sammy’s, just to name a few. Today we are honored to be on rotation at the O’Henry Hotel for the O’Henry Jazz Series in Greensboro, NC.


GEORGE AND DIXIE PENN have performed together since they were teenagers in the 1950’s. They met while they were playing (and singing) in the Russ Carlton Big Band at the Carowood Club in Martinsville, VA. My 3 sisters and I have performed with them since we were children.



VAUGHAN PENN:  Vaughan is a successful, professional singer-songwriter who has an organic pop-rock-americana sound. She has had 54 original songs placed over 150 times in Films & Television. Notable placements include: Grey’s Anatomy, Superstore, Oprah, Bones, and The Hills.



LIZ PENN: Liz’s experience spans producing shows at Universal Studios, performing in jazz and musical theatre venues, and providing performing arts medicine for Broadway performers. Her favorite roles include: Kathy in Singing in the Rain, Val in A Chorus Line, and performing with Penn Family Music.



GEORGIANNA PENN: Georgianna is a vocalist with the Greensboro Big Band. She has performed in musical theater productions across the country, like Busch Gardens Williamsburg, and is a freelance writer.  She is the Public Relations Manager for Penn Family Music.