Dempsey Hill

Great area with many restaurants and breweries. Most of them have beautiful settings with green backdrops. The area is a little pricey and a regular hangout for expats. It’s a good spot for a quiet dinner and drinks afterward.

Expat paradise or so it seems, lots of choices for dinner or lunch. Great antique shops and quirky cool shops and my favorite rug shop in all of Singapore lotto carpets.

The hippest, most happening destination in Singapore right now. Tons of restaurants, cafes that were transformed from old British barracks. The area has Tons of history, esp during WWII. Check out The White Rabbit, a refurbished British chapel that is now a brunch hotspot

Dempsey Hill is one of my favorite places to go for dinner. The place has been completely revamped from the old days, when it was old army barracks. Now in place are trendy bars and restaurants and some furniture and specialty stores. Its frequented by lots of expats, yuppies and trendy locals.
My favorite places to go here would be PS Café and Margaritas. Restaurants can be a bit pricey, but not what you wouldn’t expect in other restaurants around the area. A nice place to grab a drink at bar, then walk over for dinner in a nice restaurant. It can be a bit tricky to get here though, unless you drive or take a cab; as its up a hill and no buses or trains come directly here.

A former British Army Camp, Dempsey Hill is harder for people without cars to get to, even though it’s just a few minutes away from the Botanical Garden and Holland Village or Orchard Road. It’s known for great food, though (sigh) sadly in my case, most are not halal. I like going to Dempsey Hill just to chill though. I can enjoy my ice-​cream in peace at the Ben & Jerry’s branch down here, head to Culina and Jones The Grocer to buy freshly baked bread and look at what produce is in season. I like the selections at Beauty Emporium at House too.
Antique, Asian furniture is available at several shops here, but they’re pricey. Families may also wish to let their kids loose at Go-​Go Bambini. They have a huge ball pit and indoor playground that kids love. They also have a café for visitors to relax, chit-​chat and try out the cakes and muffins they serve.
Many shops close by 6.30pm, but still, Dempsey Hill’s s nice place to hang out over the weekend. To me, it’s even better when there are less crowds on weekdays.

Dempsey Hill, a great place to retreat to after a long day of shopping or a place to have brunch before you hit the town. Surrounded by lush greenery, Dempsey Hill houses many modern bistros ranging from western to Asian food, even local flavors like the famous chili crab (Jumbo Seafood). Another great thing about this location is the free parking! Nothing comes for free, not in Singapore at least so with FREE parking offered, this place is a winner with everyone! Before the F&B culture took over Dempsey, the place was known for niche antique/​outdoor furniture retailers so if you’re looking to add a unique piece of furniture to your home, this is your go to place. Feel free to enjoy a cup of coffee while hunting for furniture!

Dempsey Hill remains my choice of destination for brunch or a chill out afternoon because of one main factor: FREE PARKING (please don’t ever take that away!). It’s a bit out of the way and a pain to get to if you don’t drive, but drivers (and me) love this spot because you never have to worry about paying an arm and a leg just for your car.
Sometimes parking is rather tight in the main lots, but if you don’t mind walking a little, there is usually a parking spot in some of the less crowded clusters. The main Dempsey Road can also get a tad crowded so here’s a hint: Minden Road leads you to the area just fine and is usually less used…
There’s also a great selection of dining places so if it gets crowded, it’s easy to just walk to the next spot. My usual choices to visit up here include House, Jones the Grocer and Wine Company.