Places to Hike in Trinidad: Chancellor Hill x Breezy Hill

Chancellor Hill is probably one of the most popular places to go walking. On any given day, you will find scores of people using it for their daily exercise. For years, when I lived in Port of Spain, I did the same. But I always stopped at the top of the hill, where the paved road ends. Actually, twice I ventured past the top of Chancellor Hill to the trail where you will see this chain. 

I followed that trail a couple times all the way across the mountain and came out through St Ann's. You can read about that here. 

But there is another hike that I had never tried before that also begins at the top of Chancellor Hill. This one is known as Breezy Hill. And from what I've been told, there's many ways to get there. You can start through the path with the chain, or you can start from a path on the left that goes past a WASA station. 

This is the path I took when I finally tried it on Sunday November 3, 2024. 

I did not know what to expect, what kind of terrain it would be, how long it was, nothing. I watched videos from other hikers who had been there before, but they were more focused on capturing the scenery and the views than detailing the length or difficulty. So, I truly did not know how hard this would be.

Ya girl started at the bottom of Chancellor Hill because I didn't think Breezy Hill was going to be long, maybe 30 minutes tops, and I wanted a good workout. I figured Breezy Hill alone was not going to be enough. Lemme tell y'all, it was enough! Without Chancellor Hill, Breezy Hill is a challenge by itself. It is short, yes. From the top of Chancellor Hill to the flag at the top of Breezy Hill is only 1.32km (.8 miles). Yes, it is less than a mile. Less than halfway around the Queen's Park Savannah. That makes it sound easy, right? WRONG. It is a grueling 1.32 km. There is no flat part of it. It is ALL uphill and steep. 

The terrain is rocky and uneven and somebody even tied a rope to assist hikers in navigating the steep terrain at one point. Bless their soul.

If I had known how difficult this would be, I would have started at the top of Chancellor Hill and not the bottom. Starting from the bottom makes the entire trek to the top of Breezy Hill 4.8km (2.98 miles). Oh, I also walked back to the bottom of Chancellor Hill so in all it was 9.6km (5.9 miles).

Chancellor Hill has had some changes since the last time I've been there. I moved from Port of Spain to the East so the last time I visited Chancellor Hill was before the Covid-19 pandemic. Now, there signs marking the distance as you walk. Those weren't there before and I don't know when they were installed. But it was like having an inanimate cheerleader encouraging you on. 

But anyway, Breezy Hill is challenging because it is steep. There are a couple places along the way where you can veer off the main path and take a side path that will rejoin the main path a few minutes later. It's just different paths to get to the same place. And none of them make the hike any easier. When
I reached a clearing, where you can look out over Port of Spain and take in the awesome views, that's where I had reached the limit of my exhaustion. 

Right here, I was DONE. 

My 16-year-old son was with me, and he too was damn fed up and complaining to turn back. We were about to turn back when I messaged a co-worker who had done Breezy Hill before to ask him how much further the flag was from the clearing. Because I would have hated to turn back and then find out I was close to the flag. He assured me that it was one more hill to the flag. I'm not sure I believed him because he previously told me it would take 20 minutes to the top. It has already been an hour. But I decided to make it over that last hill. Lo and behold, there was the flag. I almost quit literally three minutes before the end. 

Well I saw the flag, saw what there was to see and headed back out. The trek back down Breezy Hill was a lot easier. Downhills are my favorite. I practically ran back down. I also walked all the way back down Chancellor Hill and marveled that I did all that. 

I can compare this hike to the Pines at Mt Tabor. It's almost the same distance actually if you start at the bottom of St John's Road. Same sort of terrain...a paved road leading to a short but STEEP trail. But to me Mt Tabor is slightly easier. 

Also, I was told there is a second flag at Breezy Hill if you continue on past the first one. But I didn't venture on to see. I was exhausted by the time I got to the first one. 

Anyway, here's some giraffes I saw by the zoo when I finished. lol

Length: From the bottom of Chancellor Hill to the top of Breezy Hill and back - 9.6km (5.9 miles)

Terrain: Paved road leading to rocky, steep dirt trail.

Time: It took me 4 hours, 35 minutes but this included NUMEROUS rest breaks. A fitter person could probably do the entire thing in 2 hours without stopping. 
Level: Hiking groups rate this as "moderately challenging". I would give it a difficulty rating of 7 or 8 out of 10.