Labrador Nature Reserve and Bukit Chandu

Start on Pepys Road, climbing from Pasir Panjang MRT towards a restored bungalow on the ridge, drop to a sea cliff over the port by late morning, and end the day up on Henderson Waves. Most visitors to this stretch of the south ride the cable car or climb to Henderson Waves and call it done. We'd give it a full day. Labrador Nature Reserve holds 22 hectares of coastal secondary forest and the only publicly accessible rocky sea cliff on the mainland, with Second World War guns still facing the water.

Our pick runs in this order. Be at Reflections at Bukit Chandu when it opens at 9.30am and give it about an hour. Take the Circle Line one stop to Labrador Park MRT and be in the reserve by about 11am, before the heat builds. Spend the middle of the day in air-con, then climb to Henderson Waves after 5pm, when the light softens over HarbourFront. The cost is your legs. There's a steep climb at each end, and it's 31 to 33°C most days, so carry more water than feels sensible.

Reflections at Bukit Chandu

Reflections at Bukit Chandu, at 31-K Pepys Road, tells the story of the Malay Regiment's last stand at Pasir Panjang on 14 February 1942, when 1,400 men held Point 226 against a much larger force. It's a small museum in a restored bungalow, and it changes how the green ridge outside feels for the rest of the day. From Exit A of Pasir Panjang MRT, cross Pasir Panjang Road, walk about 300 metres with the traffic and turn left up Pepys Road for about 700 metres. That sounds short until you meet the gradient, so allow 15 to 20 minutes.

It's open Tuesday to Sunday from 9.30am to 5pm, with last admission at 4.30pm, and closed on Mondays except public holidays. Singaporeans and PRs get in free with a pink or blue NRIC, and so do children aged 6 and under of any nationality. Adult visitors pay S$7, concessions S$5 and a family package S$21, all plus GST, and a ticket stub from the National Museum or Changi Chapel knocks S$2 off. Payment is cashless. The bungalow is wheelchair and stroller accessible. Inside, leave the flash and tripod off and keep costume changes for elsewhere.

From the bungalow you've got a choice. If you still have the legs, Kent Ridge Park and its canopy walk make the natural pair with Reflections, out at the western end of the Southern Ridges. NUS UTown, the campus lawn at Kent Ridge, is a trip of its own from a different station. We'd head the other way, down to the sea.

A pillbox on Pasir Panjang Road

The same story has one more marker on the road below the ridge. The Pasir Panjang Machine-Gun Pillbox stands at the junction of Pasir Panjang Road and Science Park Road. The National Heritage Board says pillboxes like it were built in the 1930s to strengthen Singapore's coastal defence as part of Britain's preparations for war, equipped with machine guns and placed at intervals so that their fields of fire overlapped.

This one lay in the area guarded by the 1st Battalion of the Malay Regiment, the unit that later fought the invading Japanese troops at Pasir Panjang Ridge. It also helped protect the southern area, which held ammunition depots and Alexandra Military Hospital. NHB's war trail booklet says the pillboxes along that coastline were spaced about 600 yards apart, and that the Malay Regiment might have used this one in its fierce resistance.

It's about two kilometres from Reflections in a straight line, so treat it as its own short stop rather than a detour from Pepys Road. Haw Par Villa and Kent Ridge MRT stations are each under a kilometre away, again in a straight line, and the map link on NHB's page marks the exact spot. We'd add it if the story has hooked you.

Kent Ridge and the last stand

Back up on the ridge, the park beside the museum is where the fight is remembered. NParks's page says Kent Ridge Park is gazetted as one of 11 Second World War sites in Singapore, and that Lieutenant Adnan bin Saidi and his platoon faced a large Japanese force here. The National Heritage Board puts the battle at 12 to 14 February, and says the ridge was given up only when the regiment had fought to its last few men. A plaque at Carpark B marks the 50th anniversary of the end of the war.

The park covers 47 hectares and is open 24 hours. Its Canopy Walk, a 280-metre boardwalk through the forest at canopy level, links it to Reflections at Bukit Chandu, so you can walk between the museum and the park without going back down to the road. Only the Canopy Walk and Tembusu Grove are wheelchair accessible, because the rest has steps, and parking is free. Kent Ridge and Pasir Panjang are the nearest MRT stations.

Down to the Labrador shore

Labrador Park (CC27) is also a short Circle Line ride from HarbourFront if you're coming the other way. From the station, follow the signs down Labrador Villa Road for about 10 to 15 minutes to the park. By taxi, ask for Carpark B, which has 60 lots, is open 24 hours and charges fees. Carparks A and C are there too.

The nature reserve is open 7am to 7pm daily, and entering or staying after 7pm isn't allowed. The wider Labrador Nature Park around it, with its lawns and carparks, stays open 24 hours. Inside the reserve there's no cycling and no drones. Pets aren't allowed in the reserve itself, though they can use the remaining boardwalks and park areas. Groups of more than 30 need a permit, applied for at least a month ahead. Macaques sometimes work the path, so keep food zipped away in your bag.

Dragon's Teeth Gate and the guns

Follow the Keppel Coastal Trail, an elevated, wheelchair-accessible boardwalk through restored beach forest, with the sea alongside and wildlife close enough to watch. Listen for oriental magpie-robins and black-naped orioles, and look out for sea grape and fish-poison trees. Plantain squirrels are bold here and will make off with a plastic bag if you let them, so hold on to yours.

Down on the shore stands Dragon's Teeth Gate, or Long Ya Men, a replica of the rock that once marked the entrance to Keppel Harbour. The British blew up the original in 1848 to widen the channel for modern ships, which is one way to settle a navigation problem. The copy is a monument to that maritime past, so admire it from the ground. Around the headland, gun batteries and the old fort show why this coast has always been more than a park. When you need a sit, ComChest Green is a 1-hectare therapeutic lawn for seniors and for anyone else who needs a bench.

Three stretches of the coast are closed. Berlayar Creek boardwalk is shut for improvement works until March 2027, so leave the mangrove loop out of your plans until then. The Casemate and the Rocky Shore are closed for public safety, and have been in stages since slope works in 2023. You can still photograph the Casemate and the Rocky Shore from the open path, and the Keppel Coastal Trail gives you plenty of shoreline without them.

Seah Im and the art museum

Ride the Circle Line to HarbourFront for lunch at Seah Im, under the bus interchange. It's a hawker centre, a cluster of stalls cooking to order around tables you share with strangers, and it's where we'd eat before the Henderson climb or once the cliff has worn you out. VivoCity is close by when somebody in your group needs a mall.

When the heat peaks, trade the ridge for the cool galleries of the Singapore Art Museum at Tanjong Pagar Distripark, 39 Keppel Road. It's open daily from 10am to 7pm, with last entry at 6.30pm, and the nearest station is Cantonment MRT, Exit 1. Because it opens on Mondays, it's also the swap when Reflections is closed, or when a storm makes the ridge a poor idea.

Hiroshi Sugimoto's Form Is Emptiness runs until 11 October, at S$20 for adult visitors. Upstairs in Level 3 Gallery 3, Maria Taniguchi's Afterimage stays until 22 November and comes with general admission, free for Singaporeans and PRs. Afterwards, pair the museum with tea on Neil Road in Chinatown, which beats a 5pm Henderson climb under storm clouds.

Up to Henderson Waves

Henderson Waves is 274 metres of timber bridge, 36 metres up and open 24 hours. We'd aim for 5pm to 7pm, when the heat eases and the light turns gold, rather than midday. From HarbourFront, Marang Trail climbs 800 metres of steps to reach it, about 15 steep minutes. If you'd rather ride, the cable car costs a fare, runs from about 8.45am to 10pm with last boarding at 9.30pm, and earns it if the port lights are the point.

The quieter way to Henderson stays high. From Reflections, walk the ridge to HortPark at 33 Hyderabad Road, the gardening end of the Southern Ridges: 10.7 hectares, free and open 6am to 11pm. Its visitor services counter keeps shorter hours, 9am to noon and 1pm to 5pm on weekdays and 8.30am to 12.30pm on weekends and public holidays, while the park stays open. Labrador Park MRT is the nearer station, and buses 51, 61, 93, 97, 100, 166 and 963 serve it. From HortPark, the Forest Walk carries you on to Henderson along its metal canopy walkway.

Two detours if you have time. Below the ridge, Gillman Barracks fills old colonial army blocks with contemporary galleries. It's free to wander, but check which galleries are open that day. And if the cliff has turned you into a water person, the Sentosa Boardwalk is a free walk across to the island from HarbourFront, and Palawan is free once you're on Sentosa.

After the reserve closes at 7pm, Clementi Woods further west is open 24 hours if you still want grass underfoot. So is West Coast Park, 50 hectares with nine barbecue pits and tankers out on the strait, and it has a morning of its own. Wherever you end up, finish facing the water. The guns on Labrador's headland were put there to watch it, and it's a far better view without the war.