Old Entrance Gateway, River Wall and secondary Gate of Monmouth Boys School

The Old Entrance Gateway, River Wall, and secondary Gate of Monmouth Boys School is a structure built from roughly squared and coursed old red sandstone, featuring dressed quoins and other dressings made from Forest of Dean sandstone. The castellated wall extends west along the A40 for about 75 meters from Wyebridge Street and then returns north to connect with the Design and Technology Centre on Wyebridge Street. This wall stands approximately 3 meters tall and is topped with coped castellations that rest on a band, both made of Forest stone.

The old entrance gate, which is now blocked, is positioned at an angle across the corner and features a 4-centred arch flanked by octagonal turrets with pepper pot tops. Above the arch, there are the arms of the Worshipful Company of Haberdashers, accompanied by supporting shields. To the left of the main gate, there is an arched footgate that includes a decorative double wrought iron gate dating from the 18th century, which was relocated from Haberdashers' Hall in London.