Walks in Woollahra

Gap Park Historic Tramway Trail

Take a stroll along the new accessible pathway along the historic tramway route through Gap Park connecting Military Road and Old South Head Road.

Art and Culture Walks

Take a DIY arts and culture walk of Paddington North, Paddington South, Woollahra or Double Bay and explore local galleries, public art works and historic plaques at your own pace.

Bondi To Manly Walk

The Bondi to Manly Walk, an iconic 80km walk around Sydney Harbour that starts at Bondi Beach, crosses the Harbour Bridge and ends at Manly Beach has officially opened.

Harbour Walk - Rushcutters Bay to Rose Bay

This walk takes you through some of Sydney’s most exclusive harbourside locations from Rushcutters Bay to Rose Bay and is the first of a series of connected harbour and coastal walks.

Harbour Walk - Rose Bay to Watsons Bay

The walk offers a great opportunity to explore the rugged cliffs, secluded coves, parkland and remnant bushland of Sydney Harbour’s southern eastern foreshores, and includes breathtaking harbour views. This walk forms the middle link in the series of connected harbour and coastal walks.

Coast Walk - Christison Park to Inner South Head

This walk emcompasses the history and romance of shipwrecks, old lighthouses, military fortifications, as well as the raw natural beauty of high windswept cliffs. It is walk the final link in the series of connected harbour walks.

Local History Walks and Talks

Discover Woollahra's rich history through engaging walks and talks. Explore local stories and landmarks through our events series or try self-guided or virtual walking tours.