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From the Darlinghurst Court House (see Darlinghurst Court House & Old Darlinghurst Gaol) follow Oxford Street as far as the imposing sandstone walls of Victoria Barracks. Turn left into Glenmore Road, which has a cluster of small but classy boutiques. Gipps Street leads to Liverpool Street, which is a winding road of elegant double-storey terraces reminiscent of some of London’s wealthier Victorian districts. Hogarth Galleries , is down Walker Lane. Rejoin Glenmore Road and follow this winding and busy thoroughfare to Five Ways, a quaint little intersection with several good cafés, including Gusto.
After coffee and a snack, head up Broughton Street to the narrow laneway and steps on your left. At the bottom of the lane turn right and walk down to steep Cascade Street. Turn right and walk uphill past Windsor Street’s incredibly narrow terraces to Paddington Street. Follow this elegant fig tree-lined avenue up to Jersey Road, passing Tim Olsen Gallery and several of Sydney’s premier addresses en route. Turn right into Jersey Road, then into narrow Caledonia Street, which leads back to McGarvie Street where several eccentric balconies overhang the narrow pavement. Turn into Underwood Street and you’ll find the Grand National Hotel and the London Tavern, both happy to serve you a well-earned drink. The latter is on William Street, which also has several boutiques.
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