When William Crawford, founder of Portsmouth, laid out the street plan in 1752, he designated the intersection of High Street and Court Street as the town center and set aside space for a parish church. In 1761, when the Vestry of Trinity Church was formed with Crawford as a member, the original church building comprised most of what is now the nave.
The first parish priest, the Rev. Charles Smith, was succeeded by a Scotsman, the Rev. John Braidfoot, who became Chaplain of the Second Virginia Infantry Regiment when the American Revolution broke out. Loyalists on the Vestry included Andrew Sprowle, the wealthiest man in the colony and the owner of the Gosport Shipyard.
When the British occupied the town, the church was used by the British garrison. General Cornwallis left Portsmouth for Yorktown where his army was defeated; Trinity's old church bell was cracked celebrating his surrender. The first native-born rector, John Emmerson. Since there was no bishop in Virginia at that time, he had to receive his Certificate of Ordination from the Bishop of London in England and it hangs in the parish hall.
In 1821 the Vestry called the Rev. John H. Wingfield who remained rector for fifty years. During the Civil War the crew of the ironclad C.S.S. Virginia (commonly called the Merrimac) worshipped at Trinity before taking to ship to fight in the first battle of ironclads against the Union ship Monitor. The Union army then occupied the city and the Rev. Mr. Wingfield’s son having refused to sign the oath of loyalty to the United States, was thrown in jail and sentenced to sweep the streets.
Over these years, the colonial pews and side balconies were removed and several fine Tiffany windows added. In the 1890’s Trinity Church was the founder of the King’s Daughters Hospital, which later became Portsmouth General Hospital. In 1893 the baptismal font in the shape of an angel, fondly called Elizabeth, was dedicated.
In the 1950s the Victorian parish hall was replaced by a modern facility. In 1976, to commemorate the American Bicentennial, a wall plaque, depicting a family from the eighteenth century and carved at the National Cathedral, was mounted above the font. By 1993 a $300,000 renovation plan which included the church, organ, and the churchyard was completed. A former rector, The Reverend C. Charles Vaché, spearheaded an effort to improve housing conditions for the poor and made Trinity’s facilities available to many groups. Today the same sense of community responsibility prevails at Trinity.
As Portsmouth expanded to the west, Trinity Church and the previous existing mission of St Stephen's in Port Norfolk together created the new St. Christopher's Mission in the Churchland area which has been an independent parish for over forty years
Most of Trinity’s priests have remained for long tenures. The Rev. Robert Huffman came to be rector in 1977 and remained until his retirement in 1993. His predecessor stayed for nineteen years until he became Bishop of the Diocese of Southern Virginia. Trinity Church could rightly be called the mother of bishops, since five of its rectors have been elected bishop.