Weymouth: the Gloucester Street heads

During my most recent visit to Weymouth, in September, I spent an hour or two wandering around the streets of the old town, streets full of characterful buildings, interesting signs and plaques, notable snippets of architectural adornment. One such thoroughfare is Gloucester Street, where I took the photographs shown here. 

By sheer coincidence, the guesthouse where I stay when I visit Weymouth, the excellent Gresham (highly recommended if you’re ever in the area – I am not paid to say that; I’m simply going by my experience of the friendly helpful hosts, the comfortable well-appointed rooms, the delicious breakfasts) subsequently posted about Gloucester Street on social media:

Have you ever noticed the faces on the buildings in Gloucester Street?
We recently heard a fascinating bit of Weymouth folklore about them.
The story goes that they date back to Weymouth’s royal days, when runners working for the King were sent around town with messages and errands. As some couldn’t read, they were supposedly directed to the right house by the face carved outside it.
Great story, isn’t it?
There’s just one problem… we’re not convinced it’s true.
We’ve been doing a little digging and, so far, the dates don’t quite seem to add up. George III’s famous visits to Weymouth were at the end of the 1700s and beginning of the 1800s, while the buildings with these particular faces appear to have come later.

 
The sculpted, and sometimes painted, heads on the Gloucester Street houses had also captured my attention, and I took the photos shown below of some, though not all of them. 

I love the idea of the folklore related by folks at The Gresham but a little online research appeared to confirm what they wrote about these houses being constructed after the years that King George III made his regular visits to Weymouth. The British History Online website reports as follows **:

The area W. of Gloucester Row was developed by speculative builders from c. 1830; the houses were more simply designed and cheaply constructed than the monumental terraces facing the bay and were intended for occupation by a lower social class. The streets in which the early stages of this development, prior to 1850, are seen are Bath Street, Gloucester Street, Park Street and Wesley Street. The houses (Plate 185) are very similar to one another in character; they are mostly of two storeys and attics with rendered brick walls and slated roofs, of one room in width and with doorways under semi-circular or segmental-arched heads. All except Monument (257) have bow windows to the first floor with double-hung sashes and moulded or dentil cornices. 

So, what is the story behind the intriguing sculpted heads? I still don’t know. But if I, or the folks at The Gresham, find out more, I’ll be sure to update this blog. 

** ‘Weymouth', in An Inventory of the Historical Monuments in Dorset, Volume 2, South east (London, 1970), British History Online https://www.british-history.ac.uk/rchme/dorset/vol2/pp330-374 [accessed 18 October 2026].