One of the older streets, Chester Street was at one time referred to as Chester Lane, and this street, along with Lambpit street and Henblas Street, formed an area of Wrexham known as The Lampit/Lambpit.
The Post Office was located at what is now the site of The Old Vaults (Long Pull) between 1786 (or earlier) and 1814, before being transferred to N° 36 Chester Street.
Between the entrance to the old Guildhall and the Rose & Crown (which stood on the southern corner of the Lambpit Street junction) was a row of tall, terraced properties, the most significant of which was the Bromfield Hotel. These houses were demolished in 1970. The Registrar’s office was housed at N° 23, Chester Street House, an early 18th century town house. Alongside N° 29 is a modern office block, built in 1991 on the site of the former Chester Street English Baptist Chapel.
The last building on this side of the road is the former chapel schoolroom which was converted into the chapel in the late 1980s. In the early 20th century, there was one other building on this side of the street, a small stone-built lodge at the end of the drive leading to Llwyn Isaf. The boundary wall and entrance to Llwyn Isa£ survives as the entrance to the Library car park and just beyond it is the old Wrexham-Chester milestone which originally stood on the opposite side of the road. Between this and the inner ring road stands the former premises of Grove Park County School, opened in 1902 and now part of Yale College.
The land on the opposite side of the road to Grove Park was, in the 1860s, used as a plant nursery which was opened to the public on Sundays and provided the town’s first unofficial park. At this time there was also a skating rink located in this area. Bodhyfryd House stood on the east side of the street, on the site now occupied by the Crown Buildings. The Red Lion stood on the corner of Chester Street and Holt Street and was re-built and re-named the Welch Fusilier. On the opposite corner was the now demolished Rose & Crown.
Wrexham Borough Council, which had previously been accommodated in Bry Y Fynnon house, purchased the old Wrexham Grammar School on Chester Street in 1883 and adapted them to become the new municipal buildings, the Guildhall. An extension was added in 1884 to house the Wrexham Fire Brigade. The Guildhall was in service until the opening of the new Guildhall on Llwyn Isaf in 1961, the original buildings being demolished in the early 1970’s.
The Saith Seren was originally the Seven Stars Hotel. Its current name Saith Seren (“Seven Stars”) reflects the pub’s reopening in January 2012 by a co-operative called Canolfan Gymraeg Wrecsam Cyf (Wrexham Welsh Language Centre Ltd). The centre provides a focal point in the town centre for Welsh speakers or learners and was conceived as a legacy of Wrexham hosting the National Eisteddfod of Wales in 2011.
In 1898 the building was rebuilt using Ruabon red brick, to a design by Liverpool architect Thomas Price. Notable features include the turret on the corner and the colourful mural on the gable facing Chester Street. Mr Price also designed the Empire Music Hall (later the Empire Cinema), which was built next door (facing onto Lambpit Street) at around the same time. The hall is now part of Saith Seren.
The former Feathers Hotel was once a busy coaching inn. You can see remnants of the stables and coach house immediately behind the building on Charles Street. The Feathers took on its present aspect when it was remodelled c.1850. The surviving structure of the original building here suggests that it was once timber-framed. Its gable end probably faced the street (with the roofline at right angles to the street).