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The back of St. Mary de Crypt is a tapestry of historic Gloucester. Standing with the ghostly residents of the church graveyard, it's possible to glimpse the Roman Gloucester of Southgate Street through Marylone arch, the Saxon Gloucester of Marylone, the medieval Gloucester of the Church of St. Mary de Crypt, the Reformation Gloucester of the Crypt school room and the Georgian Gloucester of the range along Marylone.

The Church of St. Mary de Crypt was first recorded in the early 1140s. It was extensively rebuilt in the late 14th century, and described as new in 1401. Alterations were made in late 15th and early 16th centuries, and an extensive restoration was carried out 1844–1845. Further restoration was completed on four separate occasions between 1866 and 1908, the last of which removed the unsafe tower battlements and pinnacles. Three of the pinnacles are, according to Historic England, now located in the garden of Barnwood Court in Barnwood. The only 12th-century feature still surviving is the hood mould that causes rainwater to splash away from the west entrance on Southgate Street.

Originally known as St. Mary in the south, the church acquired its name in the mid 16th century, probably from the large space under the west end. The crypt was used as a tavern from at least 1576 until the mid 1670s, then as accommodation until the 1840s. During the siege of Gloucester in 1643 the church served as a magazine and timber store.

Marylone, a derivation of Mary's Lane, runs down the north side of the church graveyard. It has it's origins in Saxon Gloucester, when it originally ran from Southgate Street to the eastern Roman wall. It meets Southgate Street under a porch formed by the Crypt School Room, built 1539 and one of the first brick buildings in Gloucester. The school was sold to the church for use as a Sunday School when new school premises were built elsewhere in the city in 1862.

The other side of Marylone to the church is lined by a mid 18th-century service range. Originally part of No. 31 Southgate Street, the range is now a separate property occupied by Café René.

To the south of the church, across a cobbled lane from Southgate Street to ruin of Greyfriars, is a gatehouse that opens out onto the forecourt of the Quaker Meeting House, both dating back to 1834–1835.