As part of Singapore’s eternal quest to be hip and happening, any area on the island that displays the remotest potential of being cool is sure to be snapped up by the urban planners at some point and re-made, re-named and re-branded.

Dempsey Road was no exception. The old British military buildings in this largely forested neighborhood have been home to antique and furniture stores for some time, the gorgeous red brick St. George’s Church, and expat football and rugby groups that play on its fields on weekends. Places like Wine Network (#01-03A, 13 Dempsey Rd., 6479-2280) are familiar establishments here; rustic, outdoorsy places where people stop by for a drink and snacks.

More recently trendy establishments like PS Café and The Hacienda moved in, bringing with them the fashionable set and pushing this neighborhood a few rungs up on the ladder of cool.

And now all this is Tanglin Village, a collection of over 30 businesses and organizations in three clusters Minden, Dempsey and Loewen—with new businesses joining this year. Here’s a peek at some of the cooler kids on the block.

NEW - Oosh & Yen Dining

(22 Dempsey Rd., 6475-0002)
A wine and dine development, this is a great place to hang out with friends. Enjoy the chill out alfresco bar and restaurant, cigar and wine cellar lounge, man-made waterfall—and superb Italian, Spanish, French, Asian and fusion cuisine to boot. Dine in style upstairs at Yen Dining, a spacious indoor Japanese restaurant with a gorgeous view of the landscape garden.

The Wine Company

(14D Dempsey Rd., 6479-9341)
Wine lovers sit up and take notice. The Wine Company has nothing but complete passion for wines and stocks an extensive variety of quality wines from most international wine-producing countries. Particular must-tries are the South African wines. Plus, you can organize events on the premises of this cozy establishment.

Linda Gallery

(#01-03, 15 Dempsey Rd., 6476-7000)
Established in 1999, this gallery specializes in contemporary Indonesian paintings and showcases works by reputable Asian artists like Jiang Shou, Wu Shaoxiang, Guo Jin and Li Zi Jian. It also provides art collectors with professional consultation.

Highwood Café

(40C Harding Rd., 6474-7282; Open daily 11:30am-11:30pm)
Highwood is a wine seller, deli and bakery all in one. It hosts private functions over the weekend and sells French-style baguettes, butternut pumpkins and corn canolas at the deli.

NEW - The Ballroom

(18D Dempsey Rd., 6479-9442)
Another innovative dining venture at Tanglin Village, The Ballroom is both a dining establishment and a dance floor of sorts for novices and experts alike. Boasting a modern interior and lots of glittering mirrors, this makes an interesting departure from an ordinary restaurant.

PS Café

(28B Harding Rd., 6479-3343)
Come here to watch the fashionistas and trendy types blow kisses—if you can get a table, that is. This uber chic café, which by the way only opens for dinner, is hugely popular and is often booked up days in advance. People come here not just for the excellent modern café food, but also for the buzz in the air.

NEW - Hacienda

(13A Dempsey Rd., 6476-2922)
This newly-open bar has already become a firm favorite with some. The brainchild of Michel Lu (the man behind Suba and Centro), Hacienda is fitted with lovely white drapes, minimalistic décor and a totally inviting alfresco area with neatly pruned bushes, fire torches, swings and candle lights. Look out for its refreshing, eclectic blend of music and the affordable fruit cocktails.