Chepstow Museum occupies Gwy House, a fine townhouse built in 1796 originally for Warren Jane, a wealthy apothecary and merchant.

The museum's displays reflect the growth and history of Chepstow as a trading port from medieval times and its location within the Wye Valley attracting many poets and painters.

Castle Terrace, originally known as Castle Parade, is an unbroken row of fourteen three-storied Georgian dwellings. The backs of the houses face Chepstow Castle and each house has a single front bow window, with rendered walls and a slate roof. At one time there was a local tradition that every bow-windowed house in the terrace was occupied by a sea captain.

This shows the area around the Chepstow War Memorial, on the left, which was installed in the centre of Chepstow on a platform level with Bank Street and raised by a flight of steps above High Street. It was unveiled on 8 January 1922.