A portion of it was in existence by the 14th century, and appears on the 1610 map of the town by cartographer John Speed.

It runs in a north-south direction, extending northward from its intersection with Whitecross Street.

[7][8] 1 Monk Street (pictured below), the former Working Men's Free Institute, is a grade II listed building.

It was built by Newport architect Benjamin Lawrence and has a facade of Old Red Sandstone and Bath Stone trim.

[1][9][10][11] The Monmouth Baptist Church (pictured below) at 3 Monk Street is an early-20th-century, grade II listed building.

The two-storey building features a Welsh slate roof, red sandstone walls, and an octagonal bell tower.

It is located on the east side of Monk Street, opposite St. Mary's Church.

[14] The Royal George Hotel (pictured below), on Monk Street, is an early-18th-century, grade II* listed building.

[1][15][16][17] Oak House (pictured below) at 6 Monk Street is a 19th-century, grade II listed building.

[1][18] 7 Monk Street, on the east side of the road, is also referred to as Ty Mawr.

[6][7][25][26] The Masonic Hall (pictured below) was converted from a theatre by George Vaughan Maddox in 1846.

A curved wall adjacent to the entrance of the Masonic Hall is thought to be indicative of the site of a portion of Monk's Gate.

[1][3][27][28][29] 11 Monk Street has two listings in the records maintained in the collection of the Royal Commission on the Ancient and Historical Monuments of Wales.

11 Monk Street, the second listing for this address, is also referred to as Fitzroy House and The Gatehouse(s).

Cadogan House is remarkable as the site of discovery of a 15th-century kiln which produced floor and roof tiles.

The late Georgian building was listed due to its special architectural interest.

[6][40] Chapel House (pictured below) on the west side of Monk Street, at the level of the Parade, is an 18th-century, grade II* listed building.

The garage was formerly his warehouse, and the four adjacent cottages (pictured below) had provided housing for his workers.

Constructed of Old Red Sandstone, the current house is the surviving remnant of the County Gaol, and was its gatehouse.