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Kent Ridge Park is actually the end point of my favorite hiking trail. It start in Mount Faber and a good 4.5 hours and many breathtaking views later, you end up at Kent Ridge. If you're okay with parking your car at Kent and taking the metro to Faber, you would enjoy this hike a lot!
Changi beach trail!!
Bukit Timah is probably the main spot if you want some verticals in your hiking. There are trails that go all through the central catchment area and even linking to macritchie reservoir park
The other main place is Pulau Ubin via a short boat ride. Nice quarry lake view and less human density.
1. Southern ridges whole trail
2. Dairy park/Mandai trail
3. East Coast park end to end
4. Pipeline trail
5. Coast to coast trail