Heritage Walks in Woollahra

The Woollahra local government area has some of the best harbour and heritage walks in Sydney. From dramatic clifftop trails to quiet foreshore paths and historic streetscapes, here are the walks worth knowing about.

South Head Heritage Trail — Watsons Bay

Distance: approximately 3.5km return Start: Camp Cove, Watsons Bay

Highlights: Camp Cove beach, WWII gun emplacements and tunnels, Inner South Head battery, the Hornby Lighthouse (built 1858, the second-oldest operating lighthouse in Australia), views across the harbour entrance to North Head and Manly.

The trail passes through Sydney Harbour National Park and is managed by National Parks and Wildlife Service. The path is mostly paved, with some uneven sections near the fortifications. Allow 1.5 to 2 hours for the return walk including stops. Free entry.

Hermitage Foreshore Walk — Rose Bay to Nielsen Park

Distance: 1.8km one way Start: Bayview Hill Road, Rose Bay (near the end of Vaucluse Road) End: Nielsen Park, Vaucluse

Highlights: heritage harbourside cottages, bushland sections, secluded harbour views, small beaches accessible only on foot, arrival at Shark Beach and the Nielsen Park kiosk.

A flat, well-maintained path along the harbour foreshore. One of the most scenic short walks in Sydney. Allow 30 to 45 minutes one way. Free entry.

Paddington Heritage Walk — Five Ways to Oxford Street

Distance: approximately 2km circuit Start: Five Ways, Paddington (intersection of Glenmore Road, Heeley Street and Broughton Street)

Highlights: intact Victorian terrace rows with ornamental iron-lace balconies (1860s-1880s), Victoria Barracks (1840s sandstone military complex), Juniper Hall (1824, the oldest residential villa in Paddington), Paddington Town Hall (Art Deco), Paddington Reservoir Gardens (a sunken garden built in a former reservoir).

Almost the entire suburb is a heritage conservation area. No formal guided walk exists, but the streetscape speaks for itself. The Paddington Society (paddingtonsociety.org.au) publishes heritage information and occasionally runs guided tours.

Cooper Park walk — Bellevue Hill

Distance: approximately 2km loop Start: Suttie Road entrance, Bellevue Hill (top of the Cooper Park steps)

Highlights: the famous Cooper Park steps (a sandstone staircase used as a workout route), a creek trail through 16 hectares of remnant bushland, sandstone outcrops, birdlife and a valley floor with picnic areas and tennis courts.

A surprisingly wild pocket of bushland in the middle of one of Sydney’s most expensive suburbs. Allow 45 minutes to an hour for the loop. Free entry.

Darling Point to Double Bay foreshore walk

Distance: approximately 2km one way Start: McKell Park, Darling Point End: Steyne Park, Double Bay

Highlights: harbour views from McKell Park (directly across to Fort Denison and the Opera House), the heritage Swifts mansion visible from Darling Point Road, Seven Shillings Beach, Blackburn Gardens, Redleaf Pool.

A flat foreshore walk connecting two of the Woollahra municipality’s best harbour parks. Allow 30 to 45 minutes one way. Free.

Macquarie Lighthouse walk — Vaucluse

Distance: approximately 1km each way from Old South Head Road

Highlights: the Macquarie Lighthouse, Australia’s first lighthouse site (the current tower was designed by James Barnet and completed in 1883). The lighthouse is on Old South Head Road at the boundary of Vaucluse and Dover Heights. Open for guided tours on selected dates. Views across to Bondi Beach.