Jennings and de Matteo have been dating since 2001 and are the parents of an 18-month-old daughter named Alabama.
"Asked Drea to marry me on stage tonight. I'm a lucky man," People.com quoted Jennings as saying via Twitter last Thursday night. "I'll never forget Utica, N.Y. ... She said 'yes.'"
"(Drea) was dancing on the side of the stage holding Alabama when (Shooter) called her on stage," a source told the magazine's Web site. "She was so surprised by the proposal."
De Matteo, 37, is best known for her work on TV's "The Sopranos."
Jennings, 30, is the son of singers Jessi Colter and the late Waylon Jennings.
2014: The Year in Music [PHOTOS]