Chepstow Town Trail

1. Bridge Street

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Cross Bridge Street and pass by historic Cromwell House - the home of Chepstow leather. As you walk up the street you will notice a row of 19th century terraces which provide some period charm. On your right-hand side at the top of the street stand the Powis Almshouses and Upper Church Street leads off on your left.

2. Upper Church Street

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The Montague Almshouses provide some historic interest here with a facade that dates from 1615. You need to take St Mary Street which stands opposite and leads you through a popular row of shops into the High Street. This is the main shopping street in Chepstow and therefore one of the busiest parts of town. Once you have weaved your way through the shoppers to the top end of the street you will find the imposing 13th century Town Gate and Gatehouse.

3. The Portwall

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The Place de Cormeilles, an attractive square behind the Gatehouse, is a popular spot to rest your legs while enjoying a closer look at the Portwall (a stretch of the old town wall) which runs along the square. To continue on the trail, cross over the High Street into White Lion Square and then turn downhill onto Bank Street. In front of you is Beaufort Square - once the centre of Chepstow life where markets, fairs and mayday celebrations were staged. The War Memorial stands here, next to a German submarine gun presented to the town by George V. Leave the square via Hocker Hill Street which is on the left of the National Westminster Bank. Be careful of slippery cobblestones, but don't miss out on the fine 18th century buildings which line both sides of this picturesque sloping street. At the bottom of the hill you will find Bridge Street and just a short stroll will bring you back to the Tourist Information Centre.