I attach a few photos from Winchester of sites that Stephen Hopkins would have seen in the early 1600s. (My commentary is drawn from a Walk-around Guide to Winchester, Wikipedia and other tourist naterial .)
The Westgate was built as early as the 12th century with later additions in the 13th and 14th centuries. It stands where a Roman gate stood 1500 years ago and when the defensive needs of the city declined, it was put to use as a jail and debtor's prsion. The grooves down which the portcullis would have been dropped during an emergency and five openings through missiles would have been fired on anyone attaching the gates are visible. Alas, the small museum with armour, weapons, household objects and a painted ceiling created for the marriage of Mary I to Phillip of Spain in 1554 and the roofwalk from which Winchester can be viewed are closed during the winter months and so I couldn't visit.
The Great Hall, built between 1222 and 1236 for Henry III, is considered to be the finest medieval hall in England after Westminster. Throughout its history the Hall witnessed many events and for most of its life has been a legal and administrative center and today is physically joined to the modern law courts. High on the west wall is the famous round table, made of oak and 18 ft in diameter. Dating from the 13th century it has hung in the hall from at least 1463, although at the opposite end until 1873. It is believed to have been painted for the visit to Westminster of Charles V and Henry VIII in 1522. The design is of a robed King Arthur with the names of his knights around the circumference.
The east end of the great hall was painted in the 19th c with a great tree showing the names of parliamentary representatives of Hampshire from the earliest times. On this wall are the Wedding Gates of Prince Charles.
The first cathedral in Winchester was begun in 642 by King Cenwealth of Wessex. The present version was started in 1079 with many alterations through the 16th century and today is renowned for, among other things, the longest nave in Europe. Although Stephen Hopkins' parish chursh was St. Thomas, Winchester, he surely would have known the cathedral. The Norman foundations consisted of a great raft of logs laid on bogland and by 1900 the cathedral was sinking. William Walker, a diver, worked under the foundations in black water for five years, removing the peat and decayed timber handful by handful so that the structure could be underpinned with concrete.
I close with a lovely Horse and Rider by Elizabeth Frink (1975) that looked cold in the December light rain but must be charming when the sun is out and leaves are full.