Craig Skeffington has been the band director at South Portland High School in Maine since 1994. His performing groups have won numerous honors during that time, including the Maine State Jazz Festival 10 times; the Berklee College of Music Festival three times, 1995, 2001, 2009; and MusicFest Orlando once, in 2001. In 2003, Craig was awarded "Music Educator of the Year" by the Maine Music Educator's Association. He is currently Maine's Jazz Activities Vice-President as well as a former Instrumental Jazz Chair. Craig has also served as President of the Maine Band Director's Association. In 2007, Craig was recognized by the national magazine "School Band and Orchestra" as one of the "50 Band Directors that Make a Difference".

As a New England area trumpet player, Craig has a wide variety of performance credits. These include working with Natalie Cole, Barry Manilow, Colin Raye, The Glenn Miller Big Band, and touring with The Artie Shaw Orchestra. As a member of the New Hampshire based Seacoast Big Band, Craig has performed with artists such as Bobby Shew, Louis Bellson, Bob Mintzer, Frank Foster, Clark Terry and Bob Florence. As a member of the Maine Based Portland Jazz Orchestra, Craig has appeared with both the New York Voices and Wayne Beregeron.

As a composer and arranger, Craig has studied with Bob Florence, Toshiko Akioshi and Don Stratton. His pieces appear in the most recent JW Pepper Catalog and NYSSMA manual, as well as having been reviewed in the IAJE Journal. In December of 2007, his music was programmed at the prestigious Midwest Band Clinic in Chicago.

Craig is currently an adjunct staff member at the University of Southern Maine where he teaches Jazz Arranging. Craig currently resides in South Portland with his wife Carrie and their two daughters, Hannah and Molly.