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Past the castle, at the top of Dark Lane, is the parish church of St Mary. Originally a 12th century building, the oldest surviving parts are two 13th century windows in the south wall. Local legend says that Henry Tudor was baptised here but there is no documentary evidence to prove this claim.

St Mary's sits in what was known as the West Ward, the earliest part of the town to be developed. When the castle was still a motte and bailey, the houses here would have been built of wattle and daub. When the alarm bell was rung the people would run to the castle for safety.

Walk down the Main Street of the town. Most of the buildings date from the Georgian and Victorian era. The building alongside the Clock House Tower (now a nightclub and shop), was originally the town's Assembly Room. Later it was the site of . William Haggar was a pioneer filmmaker whose - filmed largely in nearby Pembroke Dock - is now regarded as a classic of early silent film making.

A dip in the road beyond Orielton Terrace - known locally as the Chain Back - may have been the location of an early defensive ditch but this became redundant when the town walls were built. Behind the York Tavern is a medieval building said to have been used by when he was preaching in the area.