Eskelin's grandfather was the musical director of the church and played the pedal steel guitar in services while performing on the electric guitar professionally in Baltimore during the late 1940s and early 1950s. Baltimore had a rich musical legacy sustained by musicians such as saxophonists Mickey Fields and Gary Bartz. Musicians from New York often passed through Baltimore to perform on the weekly Sunday afternoon Left Bank Jazz Society concert series presented at the Famous Ballroom.
Eskelin had opportunities to sit in with locals such as Fields as well as internationally renowned artists such as Bartz, Pepper Adams and Woody Shaw.
Ellery Eskelin Music Reviews
Early performances as a leader took place at various jazz clubs such as "The Bandstand" and "The Closet" run by saxophonist and entrepreneur Henry Baker, who had a long history in the Baltimore music scene having known Lester Young, Cannonball Adderley, Miles Davis, Red Garland, John Coltrane, Clifford Brown and many others. Baker predicted that the young saxophonist would one day become "a great tenor saxophone player". At around this same time Eskelin met drummer Harold White (formerly with Horace Silver) and began performing regularly in White's quintet along with trumpeter Tom Williams.