Paid performers for the concert are pianist and vocalist John Margolis and guitarist, pianist and vocalist Rod Stone and his wife, vocalist Carrie Chillis Stone.
The concert will be the third benefit performance given for the theater this year, says Pat Wolford, president of the theater's board of directors.
"This is a generous thing for him to do," Wolford says, noting that Craig is putting more than $2,000 of his own money into the concert.
Funding also is coming from Craig Sealing Inc., the paving business Craig started when he was 16.
His wife, Susan, recently took over as operations manager at the company, which is giving him more time for his music.
He says his dream has been to build the business until it was self-sufficient, so he could work full time in his recording studio, Miles Beyond Music. The studio is on the Hagerstown property where the Craigs live with their 8-year-old son, Ollen, and 5-year-old daughter, Elizabeth.
Craig, 38, also has a publishing company called Miles Beyond Music with American Society of Composers, Authors and Publishers. He has written about 1,200 songs.
He recently won first place in a national songwriting contest for his instrumental composition "Fantasy Creates Reality." Craig had won other awards for his songs, but this was his first top finish.
One of the prizes in the Portland Song Writers' Association competition was a November trip to Los Angeles, where Craig got to meet Bryan Huttenhower, music manager for Steven Spielberg's DreamWorks production company.
Craig's music is being considered for the scoring of movie soundtracks, which he says is a great honor.
"It's a very tough market," he says.
While in Los Angeles, Craig also met Holly Tomas, a Scottish singer and songwriter doing her first tour of the United States.
He says Tomas liked his music, and he performed with her during one of her concerts.
Craig has been invited to perform his original music in Scotland and England, an offer he is considering.
He says his music is hard to categorize, but it stretches musical boundaries and is very emotional.
"It's a little bit of everything I love," he says.
The guitar is his main instrument, and he also plays piano, synthesizer, mandolin and drums. Craig, a self-taught performer who can't read music, says he learns by listening and memorizing.
After the benefit concert is over, he will concentrate on finishing his first CD. The sealing business has wound down for the winter, and he'll have a few months before it picks up again to concentrate on his writing.
Craig started writing songs when he was 13, and he quickly learned he could move people with his music.
"When they'd cry, you'd know you had something there," he says.
One of his first concerts was a Mother's Day performance at The Maryland Theatre in 1989.
He performed "Heaven's Greatest Gift," a song he'd written for his mother. When the concert ended, a young man told Craig he'd never told his own mother he loved her, and he was going home to do so.
"That really did something to me; I felt I'd really connected with my audience," Craig says.