Cycling Bermuda’s Railway Trail

Explore Bermuda on the Railway Trail and interact with the island's history, topography, biodiversity and—of course—locals


My first three days in Bermuda were bliss. I lived amongst the rich and famous (yes the rumours are true—Michael Douglas, Michael Bloomberg and so many other superstars live here). I stayed at the four-diamond Cambridge Beaches Resort & Spa, drank wines wildly outside of my budget, endured a massage from a stunning blonde, experienced most of the pricey tourist attractions and scarfed down as much fresh seafood as possible.

Life was good. Really, really good.

Adventure Without the Velvet Rope

Bermuda's Railway Trail

My stay at the resort was nothing short of hedonistic—precisely what I’d been banking on. But then I began to wonder if there was another side of Bermuda I should see.

Sure, I could have hopped aboard the Famous Homes & Hideaways cruise, but maybe, just maybe, it was time to take my training wheels off. Was there something beyond all those coves of powdery pink sand and the predictable tourist experiences listed on the lobby’s sandwich board? I needed a travel adventure without the velvet rope.

Rent a Bike and Hit the Trail

Bermuda's Railway TrailAnd so I rented a bicycle (US$40 for the first day), pointed my handlebars toward Bermuda’s Railway Trail and took off like a merry 10-year-old. Signs along the route explain the 29-km trail is named after Bermuda’s ill-conceived and short-lived rail line—now fondly referred to as the “Old Rattle and Shake.”

Finished in 1931, this railway line survived 17 years until it fell into such disrepair that it was deemed too expensive to maintain and so it was abandoned.

Biking in Bermuda

I rode a few blocks from my resort to Somerset Village, in Sandys Parish on the west side of the island, and found myself immediately lost. I was busy repeating my mantra, “Left is right… you ride on the left side, left side, Rhett, left side.”

But somehow, I’d missed the turn at the police station. My modest goal was to cycle nine kilometres to Gibbs Hill Lighthouse—about a quarter of the way across the island and one of the highest points—but this was not a promising start.

Beginning in Sandys

Back I went to the first part of the trail, in Sandys, and found it was as smooth as all the Dark ’n Stormy’s I had downed the day before.

The trail was paved and, once I was on it, well signed and maintained. Since it used to be a rail line, it’s a relatively flat swath that’s been hacked through the jungle, with strategic little cut-outs that tease you with peeks at the ocean, at lush gardens and at mansions that seem plucked from the pages of Architectural Digest.

Just don’t get cocky like I did and assume it’s all a snap to cycle. The trail crosses bridges, busy roads and disappears in places. Some parts are paved. Others are dirt. 

History Along the Trail & Getting Lost (Again)

But one of the wonders is the sense of history along the trail. A must-stop is Scaur Hill Fort. The panoramic views from the top of the hill are worth the steamy slog through the jungle. 

After I crossed Somerset Bridge, I lost the trail—again. This time, I was rescued by a pair of father-and-son fishermen. I obviously wasn’t the first to look baffled. Without a word, the father just pointed to the nearby stone forms that once held up a train bridge and on I pedalled.

Past multimillion-dollar pastel-painted “cottages” and postcard views of pink sandy beaches, I cycled. Until I got lost again, somewhere around Frank’s Bay, but another helpful Bermudian stopped and gave me directions. It turns out that my goal, Gibbs Hill Lighthouse, was right around the corner, beaming like the beacon it has been for 164 years. 

Gibbs Hill Lighthouse

Gibbs Hill LighthouseMany of Bermuda’s attractions are pricey, but not at one of the world’s oldest cast-iron lighthouses.

For a paltry US$2.50, you can visit this unusual lighthouse and discover that Bermuda’s natural limestone wasn’t strong enough to support the 2.5-tonne beacon, so cast-iron was used to build it in 1844.

Finally, after puffing up 185 stairs, 110 metres above sea level, I could see it all: the brightly coloured homes that look like jelly beans, the ferries shuffling folks around the island, the kite-boarders and yachties and those absurdly blue waters that caress the island. 

I confess, it took me two hours to cycle all of nine kilometres, but it was precisely that adventure that connected me with locals who not only showed me the way, but gave me the key to chunks of their past.

And the adventure was good. Really, really good.