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At the eastern end of the Balmain peninsula is the Darling Point Wharf, overlooked by manicured Thornton Park. A sign tracing the route of the Balmain History Trail can be found near the bus stop. On Darling Street, check out the former Dolphin Hotel and the Waterman’s Cottage. To the south, Peacock Point offers great views over Millers Point, Darling Harbour and the Anzac Bridge. Mort Bay Reserve to the north features two massive ships’ propellers and views over the ferry and tugboat maintenance yards in Mort Bay.

Darling Street runs from the wharf in Balmain East to Victoria Road in Rozelle. It’s a steady uphill climb from the wharf past narrow Victorian houses until you reach the friendly London Hotel, just before a large roundabout. En route you pass the childhood home of former New South Wales premier Neville Wran, No. 117, and the 1854 Watch House at No. 179, the oldest in Sydney. Find Gladstone Park past the roundabout, and St. Andrew’s across the road, which hosts the Balmain Markets every Saturday. From here on it’s boutiques, cafés, bookshops and salons all the way to the Victorian court house, Town Hall, Fire Station and Library (see Storytime Readings).

This lovely reserve on White Horse Point, overlooking Cockatoo Island, is best known for the Dawn Fraser Pool, one of Sydney’s oldest municipal pools. Dawn Fraser is a local legend, as much loved for her candid take on life and wild streak as she is for having dominated the pool at the 1956, 1960 and 1964 Olympic Games, leaving 40 world records in her wake. Although prone to tidal fluctuations, the pool is pleasantly unpretentious and a good place to strike up a conversation with an old-time local.

This area has some lovely Colonial homes, a small shopping village on Rowntree Street and Birchgrove Park, the site of Australia’s first Rugby League match in 1908. The northern tip of Birchgrove is known as Yurulbin Point, formerly called Long Nose Point, which, along with Manns Point, forms the mouth of the Parramatta River. Yurulbin Park has spectacular views of the Harbour Bridge, and an interpretation board near the ferry wharf provides interesting details on the area’s Aboriginal heritage.

The largest of Sydney Harbour’s islands has been used variously since 1839 as a granary, prison and shipyard. The island’s granaries were cut deep into the sandstone by some of the colony’s most recalcitrant convicts, some of whom hailed from the infamous Norfolk Island penal colony. Convicts were quartered on the island until 1871, although several escaped, including the bushranger nicknamed “Captain Thunderbolt.” Fitzroy Dock was completed in 1870, and Sutherland Dock in 1890. From that time on it was a major shipyard, especially for the Australian Navy during both World Wars. The island is managed by the Sydney Harbour Federation Trust (see The Islands), who also run tours.

Northeast of Balmain, Goat Island was one of Bennelong’s (see Sydney Opera House) favourite picnic spots. In the 1830s it was used as a gunpowder magazine and convict barracks. One prisoner, Charles “Bony” Anderson, tried numerous times to escape, receiving 1,200 lashes for his troubles. He was chained to a sandstone “couch” for two years. The island later became a base for the Water Police and Fire Brigade, and in 1925 shipyards were built on its western side. In the 1990s it was the film set for the TV series Water Rats . Boasting fantastic views of Sydney Harbour, the island and its tours are both managed by the National Parks and Wildlife Service (see Sydney Harbour National Park).

Designed by Drake and Walcott and built in 1888, the style of this ornate building is described as Victorian Free Classical. The structure reflects the creativity and craftsmanship applied towards significant buildings of its time. When it opened, the Town Hall was considered the best municipal building outside the city centre. Many of the Italian migrants who settled in Leichhardt became Australian citizens in Town Hall ceremonies between 1920 and 1960.

Leichhardt Post Office

Leichhardt Town Hall

Designed by James Barnet (see Martin Place), Leichhardt Post Office is no longer in use, but it is possible to admire its strong lines and severe shape from the street. It is a good example of the Victorian Italianate style, popularized in Australia by architectural pattern books and used in many homes. The tower, designed to accommodate a clock that never arrived, provides a formal divide between the public and residential parts of the building.

Named after James Norton, an English attorney who arrived in 1818 and established a thriving legal practice in the colony, Norton Street has long been the heart of this district. Much of the large estate purchased by Norton in 1834 is now the bustling shopping and dining strip that runs from Parramatta Road to Allen Street. You’ll find a range of stores with an Italian flavour, from bridal fashion to books, clothing and shoes, as well as bakeries, delis and butchers.

This kitsch development evokes reminiscences of Italy, and has a sundial and a statue of Dante based on a similar one in Verona. On the mezzanine level, you’ll find boutiques selling imported and local Italian fashion. Descending the stairs finds the piazza, surrounded by cafés and restaurants that offer wonderful, sunny positions for languid lunches. On the piazza level, Leichhardt Library contains a local history section with many photos of Norton Street, the surrounding areas and the people who once lived there.

Restaurant at the Italian Forum