One of the major benchmarks for the Cathedral in 1976 was the beginning of its Greek cultural and food festival. First known as the "Richmond Grecian Festival," this event, more than any other Church activity, raised the visibility of the Cathedral and introduced many Richmonders to Greek food and culture. It also introduced many to the rich spirituality of the Orthodox faith.

​In its first year, the festival was chaired by parishioner Thomas G. Ross. It began as a two-day affair held as a small-scale fundraising event for the Richmond Children's Hospital. The immensely positive response from the public led to the festival expansion.

In 1977, parishioner Theodore Deeb began to serve as festival chairman. It was not long before the demand for the tasty ethnic pastries, hospitality, culture, arts and entertainment changed the concept of the festival from a few booths to one of the biggest attractions in the Richmond area. The event quickly grew to a four-day affair that included dance troupes, Cathedral tours and lectures about the Orthodox faith, Greek film documentaries, a Greek village shopping area and live entertainment.

Deeb worked faithfully on the festival for years before his death in 1985. Like other pioneers before him, the parishioner aspired to shape worthy ideals into realities. Through his efforts, the Cathedral donated $15,000 from festival proceeds to help build a reception room at the Children's Hospital in Richmond. And under his leadership, the festival eventually would involve hundreds of volunteers and unite the Cathedral membership in one common fundraising activity. The effort would give the congregation a measure of financial independence that would enable it to more actively pursue community outreach programs. It also helped the Cathedral satisfy the mortgage on the House of Worship building in 1977.

To honor Theodore Deeb, parishioner John Coukos painted his portrait, and for years that portrait was on display on Cathedral property. Over time, Coukos painted portraits of Patriarch Athenagoras, Archbishop Iakovos, Metropolitan Silas, Parish Council member Moska Constantino and parishioner Chrysanthe Sotos. He also painted a portrait of his wife, Patricia.  Coukos gave away many of his artworks. He donated proceeds from those he sold to the Cathedral.