A walking tour of the Little Red Dot’s coastal perimeter reveals a different side of the island.

Photographs by Lauryn Ishak

An observation pod at the Sungei Buloh Wetland Reserve is backdropped by the Johor Strait and Mainland Malaysia.

I was restless, so I walked around Singapore. I don’t mean I window-shopped Orchard Road or strolled through the Botanic Gardens. I mean I walked around Singapore—a 160-kilometer loop that took me clockwise along the diamond-shaped island’s perimeter.

As countries go, Singapore is small; it could fit eight times into Bali. Former Indonesian president B.J. Habibie is attributed with first calling the city-state a “little red dot,” a gibe that Singaporeans have proudly come to own. Yet however miniscule it looks on a large-scale map, when measured in footfalls, Singapore can start to seem boundless, especially thanks to an equatorial climate that wraps the walker in what can feel like steamed towels.

In my two years of living here, no Singaporean I asked had ever heard of anyone walking around the entire island. Too hot, they’d say, and in such a small country, what was there to see? As it turns out, another side to Singapore, hiding in plain sight.

I choose a ceremonial starting point: Changi Airport, located on the island’s northeast corner. After stepping out the door marked Arrivals, a man asks me for directions. He’s in town from the Philippines to raise money to build a luxury cruise ship named Magellan, after the 16th-century Portuguese explorer. Kismet, I think, picturing my fellow circumnavigator; what an auspicious way to begin. Then the man reminds me that Magellan was killed shortly after arriving in the Philippines in 1521. So much for good omens.

It turns out to be harder to walk away from the airport than to board a flight. The sidewalk ends at an expressway, and I have to skirt rushing traffic to reach the calm emptiness of East Coast Park. Here, under susurrous stands of sea almond trees, an asphalt path runs as flat and straight as a ruler alongside manicured beaches.

Much of Singapore’s shoreline is a manufactured landscape. Since independence from Malaysia in 1965, the country’s area has grown by more than a quarter via land reclamation; Changi Airport, like this entire coastal park, sits on infill. As does the trailside Belly View Café, whose name I puzzle over until the white underside of a departing 747 roars overhead. To my left, container ships dot the Singapore Strait, with the Indonesian island of Batam rising in the distance. Some 1,400 cargo vessels squeeze through this 16-kilometer-wide corridor of water every day, making it the world’s busiest shipping lane.

The walking path dead-ends at a naval base. A young private manning the gate asks if I am here to visit its museum. I didn’t know there was one. “You’re walking around Singapore?” he says with a laugh. “At the end of basic training, we were forced to march 20 kilometers along the coast. That was torture enough.”

At the Navy Museum, we stand in air conditioning so cold that my sweat-soaked T-shirt quickly turns clammy. The private hands me a drink box of chrysanthemum tea. I feel like a child on a field trip, sipping through the tiny straw as I walk a 1,300-year timeline of Singaporean history. Other exhibits underscore the country’s dependence on the sea. The port facilities here unload 60,000 containers each day, whose contents include 90 percent of Singapore’s food.

Beancurd with shimeji mushrooms and tea at Beaulieu House in Sembawang Park.

Most of the island’s drinking water, too, is imported, via pipelines from Malaysia. Eleven sweltering kilometers west of the naval base, I stop at a water reclamation plant equipped with a maze of big pipes and valves. Singapore aims to be water independent by 2060, when its import agreements expire; two-thirds of its land area is laced with catchment reservoirs, drainage canals, and desalination plants. Parched, I gulp down a bottle of the plant’s complimentary “new water,” as it calls recycled wastewater strained through membrane fibers 1/100th the width of a human hair. The taste betrays nothing of its origin as sewage, but I make a mental note to start carrying my own bottle of H2O.

For the next 16 kilometers, I walk past litter-free beaches filled only with palm trees and the occasional sandcastle. One of the latter is marked with a tiny Singapore flag and the message: FROM NOTHING TO SOMETHING. The rising tide takes gentle bites from its base.

I can see the day’s endpoint ahead: the downtown skyline, punctuated by the 42-story-tall Ferris wheel of the Singapore Flyer and the unmistakable profile of Marina Bay Sands, its three glassy towers linked by a rooftop pool and observation deck. Along the trail there is no advertising or graffiti; Singapore is the rare Southeast Asian city that looks better in the daytime than in the masking, neon-lit night.

The path leaves the coast at Gardens by the Bay, an oasis of greenery built on sand dredged from the sea. The bay it overlooks was transformed into a freshwater reservoir a decade ago with the damming of the channel that once connected it to the Singapore Strait. Walking the path atop the Marina Barrage, as the dam is called, brings cooling blasts of sea breeze and—surprisingly—snippets of the Frozen anthem “Let It Go” wafting in from the children’s water park at Gardens by the Bay.

I limp into the Marina Bay Sands casino and thread my way through a labyrinth of 5,000 slot machines to the free soda fountain. Nearby, a roulette table sits empty. After a quick Google search on my phone I place small wagers on 4, 21, 15, and 21—the month, day, and year that Ferdinand Magellan met his end on a Philippine beach. The croupier spins the wheel, whizzing the ivory ball in the other direction. It rattles into the pocket marked zero. Which is as much energy as I have left at the end of this day’s 30 kilometers.

The same restaurant’s century-old facade.

Sleep is a reset button; after a restful night at home, I restart my circumambulation from the casino’s front door.

Across the bay, water spills from the mouth of a three-story Merlion statue, misting the selfie sticks angled toward its lion head and fish body. But I’m less interested in Singapore’s mascot than I am in the smaller figure of Sir Thomas Stamford Raffles that stands a short walk away on the north bank of the Singapore River. The statue’s plinth marks the spot where, in 1819, Raffles landed and “with genius and perception”—the plaque reads—“changed the destiny of Singapore from an obscure fishing village to a great seaport and modern metropolis.” The longest period Raffles spent on the island was only eight months, but in that time he laid the groundwork for the future British colony. No tourists snap photos of his statue today; the man is most familiar as the namesake of the nearby Raffles hotel, where, in 1915, a bartender invented the Singapore Sling.

It’s too early for a glass of gin-infused fruit punch, so I cross Cavenagh Bridge—a cast-iron span shipped in pieces from Glasgow and erected here in 1870—and walk along Boat Quay’s stretch of repurposed 19th-century shophouses. Turning away from the river, I enjoy the comparative coolness of the skyscraper-shaded financial district before arriving at the former Tanjong Pagar train station.

A hole in the perimeter fence lets me into the echoing, Art Deco building. Shuttered since 2011 when the railway’s terminus was moved 25 kilometers north to the Malaysian border, its track bed is now a dirt trail called the Green Corridor. Ten times longer than Manhattan’s celebrated High Line, this unmanicured parkland is my favorite spot in Singapore, leading hikers and bikers through lush terrain behind restored colonial-era villas. There are more butterflies here than people. I’ve never paid much attention to butterflies before, but solitary walks sharpen the eyes, and now I stop mid-stride to differentiate between a spotted leopard lacewing, a red painted Jezebel, and a tan coconut skipper.

Needing to get back to the coast, I climb a bank thick with sedge that conceals a bright green grass snake. The creature seems just as startled as me. Grass snakes aren’t venomous, but I remind myself to stick to the beaten path in the future; Singapore has its share of kraits, cobras, and vipers too.

The only danger I face on the 10-kilometer Southern Ridges trail between Mount Faber and Kent Ridge Park lurks above—a sign shows a plummeting spiky fruit and warns BEWARE OF FALLING DURIANS. The zigzagging route takes me across the sinuous, 12-story-high Henderson Waves pedestrian bridge, down a series of iron walkways through a cicada-filled meadow, and then up again to Bukit Chandu (Opium Hill). It was on this spot in February 1942 that 13,000 Japanese soldiers overran the last line of Singapore’s defense. The British surrendered the following day, and for the next three years the island went by the Japanese name Syonan-to: “Light of the South.”

Reminders of Singapore’s brutal wartime occupation dot the coast, from former prisoner-of-war camps to memorials honoring the thousands of civilians killed at the water’s edge. I’d read up on this history, but until I walked its routes and faced its sites, I had not appreciated how hopeless residents must have felt against the Japanese onslaught. The island, then dubbed “Fortress Singapore,” was in fact lightly defended by the British, who woefully underrated Japan’s capabilities.

Walking across an old iron railway bridge found along the green corridor.

Walking west on Pasir Panjang Road, I pass a group of migrant Sri Lankan construction workers lunching in the shade of an old British machine-gun pillbox. A quarter of Singapore’s 5.6 million people are foreign laborers, here on temporary passes to perform grunt work and provide childcare.

Migrants have long shaped Singapore’s development. Take, for example, the Burma-born Aw brothers, who in 1937 funneled some of their family’s Tiger Balm fortune to build a park that recalls a California beach resort—only this one is themed around hell. The grounds of Haw Par Villa are filled with sculptures that illustrate Chinese and Buddhist morality tales. I have the place to myself; these days, Singaporeans prefer an air-conditioned mall to gruesome dioramas depicting the Ten Courts of Hell.

For the next nine kilometers, I feel like I’m the one who’s on trial. Jurong Port’s tar-scented air mixes with the mosquito repellant, sunscreen, and sweat vaporizing off me. I plod past plants churning out the raw materials upon which modernity is made: cement factories, chemical tankers, and petroleum refineries. There is no place to sit and rest, but up ahead, a sliver of silver sea urges me on. To a walker, the ocean is four-dimensional, an undulating body of sparkling light, cooling mist, salty taste, and sshhing sound.

The road, alas, turns inland, and I leave the shade of cannonball trees to face a forest of 13-story apartment buildings. More than 80 percent of Singaporeans live in HDB (Housing & Development Board) public housing blocks such as these. Most of them own their own flats, giving Singapore one of the highest rates of home ownership in the world. HDBs are a marked upgrade from the wooden kampong houses that were prevalent here as recently as two generations ago. Yet from the outside, their function-over-form design looks incongruent against the landscape. I limp through an office park filled with their glassy, upscale cousins—one building is named The Strategy; another, The Synergy—and end the day at an MRT station flanked by three shopping malls. Stuck behind a plodding throng of bag-toting shoppers, I realize that today, across 30 meandering and often solitary kilometers, I have spent no money. Walking is free.

The next morning, I dodge commuters and step out of the same station—Jurong East—happy to be heading away from the workaday crowd. The next 16 kilometers take me farther west, along former mangrove swampland that was once the domain of Malay settlements and, later, plantations where Chinese migrants grew pepper and rubber trees. In the 1960s, the Singapore government enticed people to move here to work at factories churning out everything from sugar to steel to ships.

These “pioneer” villages are now HDB estates, but their legacy lives on in streets named for former plantations and in schools such as Frontier Primary, whose posted motto could also be Singapore’s: FRUGALITY AND HONESTY. Nearby, the Khong Guan Biscuit Factory scents the neighborhood with the smell of cookie dough. The morning sun already feels hot enough to bake them on the sidewalk.

Afternoon fishing at the Changi Boardwalk.

I turn off Corporation Road and follow a drainage canal to the Pioneer MRT station. Beyond this, the horizon shows only clouds; at last I’m turning north to walk Singapore’s least-populated fringe.

A tile-roofed Chinese archway stands marooned amid a swath of green lawn. It once marked the entrance of Nanyang University, Southeast Asia’s first Chinese-language college. The school was subsumed by the National University of Singapore in 1980, during an era when the state began promoting English as the island’s lingua franca. Today, the former campus is part of Nanyang Technological University, a collection of curving, modern buildings with plant-laden walls and rooftops. After stopping in the shaded courtyard of one called The Hive—its shape evokes that of a bees’ nest—for an iced coffee, I fall in behind a row of young men in fatigues who are beginning basic training for the two years of military service all male Singaporeans must serve after high school. We march together for a couple of kilometers before they peel off toward their camp, and I soon find myself facing a landscape of tombstones.

With 300,000 graves, Choa Chu Kang is Singapore’s largest cemetery, and the only one still accepting burials. In a place that often feels like a virtual city made not of bricks and mortar but of an ever-pulsing network of global trade routes, it’s oddly reassuring to watch people laying roses and lighting incense in remembrance of the generations that came before. Yet even the afterlife is transient in Singapore. Due to space constraints, burial here is limited to 15 years, after which remains are exhumed and cremated.

And then the weather turns. Dark clouds sweep overhead, lightning bolts stab the horizon, and claps of thunder roll over the low green hills of the Western Water Catchment district. I dodge sharp pencils of rain before ducking through a hole in a hedgerow, Peter Rabbit–style, onto a road lined with egg farms, where I shelter against the wall of a clucking barn.

The next 10 kilometers run straight along wide, empty Lim Chu Kang Road to the island’s northernmost point. A detour down a dirt lane delivers me to the small inlet of Sarimbun Beach; this is where Japanese soldiers first landed in Singapore on February 8, 1942. (The British were caught unawares; they had expected the attack to come from the opposite side of the island.) A pair of stray dogs bark ferociously at my approach. Beating a retreat back to the road, I follow the asphalt until it dead-ends at the Johor Strait. Just beyond, a ramshackle jetty reveals the water through the gaps in its planks. The Malaysian coast looks a leisurely swim away. A sign on the dock warns: DANGER CROCODILES.

This scuppers my plan to thread through the mudflats and mangroves to reach the remains of a rubber-plantation bungalow. So I take the long way around by road. Originally built in the 1920s and abandoned for the past decade, Cashin House is a shell of moldy ceilings and exposed wiring perched on stilts over the strait. Despite its decrepitude, it’s still a beautiful spot, with wooden shutters filtering sunlight and the sound of water lapping gently below. In a landscaped country where the most common billboard reads LET’S MAKE SINGAPORE OUR GARDEN, it’s rare to see a spot of coastline where nature is allowed to take its course.

Looking down on the courtyard of the Hive building at the NTU campus.

The next few kilometers take me past farms raising frogs, dairy cows, koi, wheatgrass, and goats before depositing me at the Sungei Buloh Wetland Reserve, a 200-hectare sanctuary for birds, otters, wild boar, and more than two dozen mangrove species. I wind through the park on a wooden boardwalk, appreciative of the shaded tree canopy and the informative signs that tally the cost of Singapore’s breakneck modernization. Only five percent of the island’s original forest remains; 89 percent of its native plant species are extinct, or threatened by extinction.

By the end of this day’s 27 kilometers I’m wishing I had some Tiger Balm to soothe my aching feet as I shuffle across the Kranji Reservoir dam and past shopyards piled with gears and cogs. The jumble resembles a heap of dinosaur vertebrae—fossils of Singapore’s manufacturing industry.

A downpour halts me the next morning, and I wait out the rain in a crowded café by the Turf Club horseracing track. I place a pack of tissues on a seat to hold my place, the Singapore way, and stand in line at the counter to order the typical island breakfast: fish ball noodles and kaya toast washed down with strong coffee cut with condensed milk.

Despite blistered feet, sore legs, and a sunburned neck, I want to keep walking, perhaps because I’ve just ingested so much sugar. Also, my walk’s end is within sight, at least on the humidity-tattered map spread atop the table. Tracing my progress with a finger, I realize I am two-thirds done. On the map, Singapore’s upper coast slopes southeast; my route appears to run downhill from here. Only 60 kilometers to go.

A path through Woodlands Waterfront Park steers me around the Johor–Singapore Causeway, the kilometer-long land bridge that extends to Malaysia. It’s also one of the world’s busiest border crossings, carrying 200,000 vehicles each day. With traffic at a standstill, I turn east on Admiralty Road and pass a mosque, then a church and a prison, before entering another industrial estate. It smells of gasoline (Senoko Energy), cigarettes (British American Tobacco), and soy sauce (Kikkoman).

After a row of semiconductor plants, the landscape turns lush and the road signs bear the names of British Empire outposts: Malta, Auckland, Delhi. Once home to a naval base, Sembawang is now a quiet bedroom community of restored black-and-white bungalows and trimmed lawns. The only sailors posted here are U.S. Navy personnel assigned to a duty station providing support to the Seventh Fleet.

On the water’s edge of Sembawang Park, I decide for the first time to stop the day early. I set out on this walk to see a new side of Singapore, and here is one now: a calm, glassine slice of ocean, shaded by towering tembusu trees.

I sit and read The Singapore Grip, J.G. Farrell’s wonderful, satirical novel about a plantation-owning family on the eve of the Japanese invasion. Its colonial narrator muses that things that once seemed immutable, such as the British Empire, in fact were remarkably vulnerable to change. But just as remarkable, especially in Asia, is how much of Singapore’s past remains visible. Looking away from the water, I realize I’m sitting next to Beaulieu House, a century-old bungalow built by a mining magnate that became home to a British admiral, the Japanese military, and Singaporean naval officers. Now, it’s a Chinese seafood restaurant.

I wake before dawn the next morning—a Sunday—and lace up my sand-powdered shoes; in my mind, the penultimate leg of the walk flashes like a cursor in the middle of an unfinished sentence. Fifteen minutes later, a taxi deposits me back at Sembawang.

In the channel next to the park, Chinese women in rubber boots scavenge for mollusks at low tide. The still surface of the Johor Strait mirrors the haze-gray navy ship gliding by on patrol.

The path turns inland, tracing the edge of a canal. Doing as the fisherwomen do, I tie my shoes around my neck and mince barefoot across the channel’s mossy, mucky bottom. The next few kilometers through the curtain-drawn HDB estates of Yishun take me over a dam, alongside a military airport, and onto Punggol Barat Island. On the bridge connecting it to the mainland, I pass middle-aged birders chattering about chestnut-winged babblers. I sound just as daft to them, pointing to my own quarry: trapezoidal mounds of sand, fenced off and guarded by sentries.

Winding down the day at the waterside belly View café near Changi Airport.

America stockpiles petroleum; China keeps an emergency supply of pork. Singapore maintains a strategic reserve of sand. It’s the key ingredient for land reclamation, and many of Singapore’s neighbors, including Malaysia and Indonesia, have banned sand exports in the name of national security. Today, Myanmar is a top supplier.

Edging along the sand reserve makes me feel like I’ve stepped into an Arabian desert. Singapore takes pride in its absorption of different peoples to create a nation, but here I appreciate, too, how it literally has blended other countries—or at least, their sand—and built something new. From nothing to something, as that East Coast Park sandcastle put it.

Not every development has worked. Six kilometers east, I cross a footbridge onto Coney Island, named after Brooklyn’s waterfront in 1950. A planned amusement park never materialized here, but the name stuck. Only butterflies, birds, and wild boars call the place home.

I end the day’s 30 kilometers at the Lorong Halus Wetland, whose sweet-smelling flora belie the fact that, until 1999, this was Singapore’s garbage dump. Now refuse is sent offshore, to the landfill on Semakau Island. Today, the trail’s lone trash can sits empty; few hikers make it out to this tranquil nook along the Serangoon River. I am beginning to lament that my walk will soon be over.

The final day begins in Pasir Ris—the name means “white sands” in Malay—a mix of unspoiled coastline and semiconductor factories standing on former plantations. Walking east through an area called Pasir Ris Farmway, I eventually cross the Api Api River to a shoreline that used to be coconut groves before British Royal Air Force officers moved in; a two-kilometer-long boardwalk winds around the pretty point past their former chalets.

Inside the Cloud Forest biodome at Gardens by the Bay.

The morning silence is broken by the roar of a jet engine. Changi Beach runs north along the airport’s perimeter, and I soak my tired feet in warm, calf-deep water as planes whoosh low overhead.

I continue forward on Changi Coast Road, keeping the runway to my right. Look at the bright tails: Cathay Pacific, Asiana, SilkAir. A single puffy white cloud shields the sun as I reach the island’s easternmost point. More planes touch down: Singapore Airlines, Scoot. Turning toward the airport, I cross a canal where a languid catfish flicks its tail and leaves behind a muddy wake. I look back at the empty path behind me and see no evidence of my passing.

Usually, I find it harder to end a journey than to begin one. But this time it could not have been easier. My Singapore loop closes 160 kilometers from where it began, with one step through the door marked Arrivals.

This article originally appeared in the August/September 2018 print issue of DestinAsian magazine (“Stepping Out in Singapore”).

Seeing Singapore in a New Light