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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.

Bush Tucker Walks

Guided Bush Tucker Walks incorporate Aboriginal culture and education and are hosted by the Eastern Suburbs Organisation for Reconciling Australia (ESORA).

Double Bay Tree Trail

Discover our latest Go Slow for Mo' Nature Wellness Trail at Gap Park, Watsons Bay.

Trumper Park Trail

Trumper Park is one of our favourite local hidden secrets to escape the hustle and bustle. We have put together a 1.6km circuit to discover sunset views, magnificient Moreton Bay figs, our famous local cricketer and the tranquil pond.

Go Slow for a Mo' at Watsons Bay

Discover our latest Go Slow for Mo' Nature Wellness Trail at Gap Park, Watsons Bay.

Cooper Park Nature Wellness Trail

Head into Cooper Park to cool down along our pop-up Nature Wellness Trail. This rejuvenating experience is designed to refresh your mood, energy and focus.

Guided Walks

Guided Historic Walks are held at various times throughout the year as part of the Woollahra Libraries Local History program.

Other Walks:

Woollahra Council is an active member of the Sydney Coastal Councils (SCC). For more information on other walks, visit the SCC's Walking Coastal Sydney website.

Gap Park