Walking the Gordon Town Trail in Jamaica

Exploring Jamaica's breathtaking interior

Five years ago, my best friend Lynne Firth and I decided to see what the fuss was all about and subsequently booked a long weekend at Strawberry Hill. This luxury boutique resort is located in the Blue Mountains of Jamaica, overlooking Kingston, and is one of the Island Outpost properties founded by Chris Blackwell of Island Records.

To get to Strawberry Hill, you can either rent a car and drive yourself, or book ground transport through the resort. We chose the latter, which was a good and bad idea. It was good in that it probably would have taken us three hours to make the journey on our own, but bad in that an Indiana Jones chase sequence had nothing on the speed, coupled with hairpin turns, of our brief but memorable trip. The drivers in Jamaica are fearless, which is why I spent the better part of the ride focussing intently on a point on the car floor.

Once we got to our destination, we marvelled at its location. It is difficult to describe the beauty and quiet of such an idyllic spot. The views are spectacular, particularly from the infinity pool, and there is no television in the cottages that cling to the mountainside. Instead, you enjoy being surrounded by nature and relaxing in the truest sense.
This particular weekend booking was a package deal which included a guided tour of the Gordon Town Trail. We signed up for the second day of our stay and looked forward to seeing some of the sights.

It was drizzly on the morning we were supposed to be heading out. Despite the iffy weather, Lynne and I decided we would walk the trail, led by our Rastaman, simply known as Dave.

It all started off with a decent slope along the main road, followed by more main road that offered an incredible vista of the valley, with banana trees, breadfruit trees and coffee plants, along with bamboo and avocado, all calmly growing on an insanely steep hillside, that begged the question, how the heck did anyone manage to cultivate these things?
As we rounded a corner, a bunch of impossibly cute children were walking down from a house, led by a teenager. We clearly heard, “Look! Two white people dem!” Our Crisco-coloured epidermises stood out a mile.

I handed out some candy that I had in my bag for emergencies. The little ones were all so bright-eyed and polite, bless them – I could have stayed there all day.

Once we hit the actual trail, we got an idea of what we were in for. We had been relieved to hear it was downhill for most of the journey but had no concept of the terrain. As we wibbled and wobbled our way over foot after foot of slippery rock, mud, and plant life, all downhill and THEN some, we passed schoolchildren and adults wearing everything from simple shoes to sandals, flying by with not a care in the world. “Dey walk dis hev’ry day,” Dave explained, as he skipped over one obstacle after the next.

“My knees,” Lynne murmured.

At one point, a very pretty 10-year-old schoolgirl attached herself to us. Apparently, Tyshelle really liked maths, and social studies, and science. By the time we parted ways, I had given her my entire barrel of Smarties. What a great kid.

As far as the trail is concerned, words fail me regarding the breathtaking scenery. It makes you want to give it all up and live in the mountains. People went by with bags of produce on their heads, all friendly and charming, quite happy to stop so Dave could demonstrate to the two out-of-shape foreigners how they walked this path and carried their belongings.

At the end of it all, we had walked about six miles, and Lynne’s sneakers, alas, did not make it. She lost the soles of both.

We got a taxi back, stopping to pay J$100 so Lynne could use a toilet, and then hit the familiar winding road up the mountain to Strawberry Hill.

This driver made our first driver look like a rank amateur. As we were thrown about in the back seat like two beans in a can, he belted around corners to the soundtrack of none other than the great Michael Bolton, blasting at us from a highly digitised sound system.
“BABY, THAT’S WHAT LOVE IS ALL ABOUT (SCREEEECH, BEEP!, BEEP!), TWO HEARTS THAT FIND A WAY (HONK, HONK, ‘HEY MAN!’), SOMEHOW, TO KEEP (VRRROOOM, SCREECH, BEEEEEEEEP!) THE DREAM FROM DYING…”

After a while, we accepted that we were passengers in a game of chicken for three miles, so we just leaned back and hoped to win. We managed to return to the resort in one piece.
At the end of the day, we sat back in our cottage, watching an amazing sunset. We flew back to Cayman the next evening.

We haven’t returned to Strawberry Hill since but would absolutely go again if we had the chance. You really should go some weekend and whatever you do, reserve a tour of the Gordon Town Trail. It’s like another world out there and it is wonderful.