Hike from Lady Chancellor Hill to Mt. Hololo

On Sunday 24th October at the crack of dawn 5:45 am, I was at the bottom of Chancellor Hill gathering with my Runners and Walkers (R.A.W) teammates in preparation for our third challenge of the Venture Series, Mission Connect – Chancellor to Hololo πŸ˜ŠπŸŒ„. There were so many cars around the savannah and at the bottom of Lady Chancellor hill that we ended up parking by the Horticultural Society offices and then walked back to our starting point at the bottom of the hill (Don’t these people like their beds!!! 😴 Why are so many persons here this hour? SMH).

Overall, at the end of the morning, we covered 19km in 4 hours 31 minutes on this beautiful and scenic trail 🌞πŸ₯°.

NB. This is not a Selfie Trail or a trail that you want to do very late in the evening and risk being caught in the bush in the dark 🌚. It is also ill-advised to venture on this trail on a rainy day β˜”οΈ.

“Of all the paths you take in life, make sure a few of them are dirt”

John Muir

The trail from Lady Chancellor Hill to Hololo is a very picturesque one. On this Sunday morning, in particular, the weather was absolutely perfect and there was a cool refreshing breeze as we hiked. Mornings like this just make you grateful for the gift of life and good health and the ability to enjoy nature at its best 😍🌲.

We started walking from the bottom of Lady Chancellor Hill and after arriving at the top, we took a left turn and headed off the road and into the trail. Immediately to your left was a Wasa sign and pump, and if you take this route it is one of the ways to reach Breezy hill (see pic below with the National Flag) 😁.

Top: The view from Breezy Hill, Bottom: The top of Chancellor – Wasa sign to the left

The air was crisp, the sun β˜€οΈ was out but it was not hot as yet and the breeze πŸ’¨ was truly refreshing. On one side, we had the mountain and on the other side… a cliff.. but thankfully the start of the trail is wide. It narrows significantly after this thou, and that is when the true adventure begins 🌿.

The start of the trail

Although at times there is an amazing view of the city of Port of Spain, this is a trail where you need to pay attention as sometimesthere may have been a fallen tree or a dried-up river πŸ’¦that you are crossing with rope so stop and enjoy the view but when you are walking, watch your step πŸ‘€.

It is not all bush and ropes though, there are some times when you get a break from all of the trees, the trail clears and you get a beautiful view of the mountains all around πŸŒ„and the city of Port of Spain πŸŒ‡.

A perfect hike day

The trail from the top of Lady Chancellor Hill continued on the side of the mountain for about two hours until we emerged by a Farmer’s patch around 8.6 km into our journey. From there on we encountered some slight uphill and at around 9.4 km in we reached a concrete road and a random structure at 9.6km πŸšΆβ€β™€οΈ 🚢.

Farmer’s Patch
Concrete Road
Random Structure

At this point, we knew we were already in St. Ann’s and followed the trail until we met a sign showing the start of the Hololo part of the trail 😚. This was around km 11 and the trail begins with a descent, don’t worry there is a rope to assist you (I, however, will not want to be here on a rainy day) πŸ§—β€β™€οΈπŸ§— πŸ§—β€β™‚οΈ.

Welcome to Hololo Trail

After traversing through the Hololo trail for about 1.75 km, we finally made it out to the familiar structure at the top of Mt. Hololo, the big house 🏑 with the hydroponics farm 🌾. We were so happy to see somewhere that we recognized after being in the bush for so long… it was a sight for sore eyes and symbolized that we were indeed on the home stretch.

The last part of the adventure was just a comfortable downhill trek to the bottom of Hololo and then onto the Queen’s Park Savannah. We ended off where we started, at the bottom of Lady Chancellor Hill. (PS. We tried to take the scenic route through the Botanical Gardens  πŸŒΈ 🌼 🌻 but it was closed due to Covid, hence the detour at the end).

All in all, we covered 19 km ….. it was hard to get up in the morning for this run but in the end, it was worth it, it always is. πŸ˜€

Have you done this trail before? Did you enjoy it? 😁

Much Love,


8 thoughts on “Hike from Lady Chancellor Hill to Mt. Hololo

    1. Thank you. Yes girl it was a long scenic trail..i want to do it again soon. You just need to enjoy your beaches and waterfalls for me please lol 😊

      Liked by 1 person

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