Sir Stewart’s Castle …. A Hidden Mystery

Pre Note – Beware of the ADS at the end of the post. I suppose I’ll be going Premium soon!

I remember the first time I laid eyes on Sir Stewart back in 2011, It was love at first sight as I couldn’t help but fall for Its mystique and exuberant charm. The second trip was compliments of Ivor and KeVaughn. Backtrack to another side of Trelawny where we made that amazing discovery. My usual excited giddiness over took me as i anticipated the sight ahead. I suppose most persons would never be able to understand what could be so exciting about looking at an old ruin but for me it was my chance to mentally re-imagine history.


  • Designated Jamaica National Heritage Trust site
  • Started as a sugar plantation built with slave labour in the mid 1750’s
  • Cut-stone mansion designed like a fortress and built by James Stewart, whose son, also James, was Custos of Trelawny from 1812 and who was instrumental in the establishment of Stewart Town, in Trelawny.
  • It appears to have been a three-storey structure consisting of a cellar, ground floor and first floor.
  • Four hundred (400) yards from the castle ruins in a south-eastern direction lies a Taino site which was found and excavated by Charles Cotter in 1957.
The approach

The approach

It’s still a mystery to me why The Castle was built at that location especially since it seemingly loses any visual  connection with that breath-taking view of the sea – perhaps security was of much more importance now that I think about it.


Despite that, it claimed the land it owned!



Walking through the outhouse:


I think what I enjoyed most, aside from interpreting what the originally could possibly have been like, was capturing the framed views throughout the ruin as seen in the photos below: IMG_5 IMG_6 IMG_8 IMG_9 IMG_10



I couldn’t shake the feeling that something was different about this trip so i dug up the captures from the first visit. Not only was there a ghastly undertone as a result of an impending storm (yea – rain seems to love threatening the likelihood of my exploits) , but there was also far less ‘untreated shrubbery’ (a phrase I cleverly coined for the term bush). Hopefully their Development Proposal is still in the pipelines! Only time will tell.



See: for more info

P.S> Happy Birthday Celia! Miss you and Love you tonnnnns sis 😀

5 thoughts on “Sir Stewart’s Castle …. A Hidden Mystery

  1. LaToya, thanks for sharing this historic review. I think the photography is great and it chronicles a nice architectural storyline.

    Interestingly enough, there are many fortress-like military and religious buildings on many C’bean territories which date back to the mid-late 1700’s that are still standing and in use today, yet Sir Stewart’s Castle remains in ruin.

    Have you found out what was the cause of damage to the original structure? It looks like it succumbed to some type of attack…Was it slave revolt? The photos reveal the telltale signs typical of ruins; the attrition and prolonged exposure to disaster such as fire, earthquake, or hurricane…

    Great Work! Looking forward to more from you.

    • Thank you so much!

      I can imagine there would be. There are also quite a few others in Jamaica but this one seemed to have been built for more private use.

      It was hard to find alot of info on this place and the Development Plan didn’t say specifically how this happened. I agree …. neglect and natural disasters could have caused this. Even now it’s just sitting there slowly being covered by shrubs. Wonder what will become of it in a decade or two!

      Thank you! Hope I’ll have lot’s more to share that will catch your interest!

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