You don’t need to look far in Sydney to find a breathtaking walk to suit all seasons. Centennial Park is a pleasant meander in winter, the coastal drama of the Bondi to Coogee walk is invigorating and a warm bundle of fish-and-chips from Watsons Bay is the ideal kick-start for a chillier walk to South Head.

But you already know about those popular walks. So we’ve gathered together some lesser-known routes through Sydney and further afield that are worth exploring in the colder months.

CITY STROLLS

Glebe and Blackwattle Bay
If it’s a Saturday, start by perusing Glebe Markets for clothes, books and vintage trinkets before hopping across Glebe Point Road for a Lebanese-inspired brunch at Thievery. Swing down Bridge Road to meet Blackwattle Bay, where you can bookend your saunter round the water’s edge with a coffee from Blackwattle Cafe or a seafood lunch at the Boathouse on Blackwattle Bay.

Chippendale Arts Walk
For an easy urban stroll with cultural leanings, join a free, monthly Gallery Walking Tour around Chippendale. Laid on by Chippendale Creative Arts Precinct. Make sure you find time to refuel at the White Rabbit’s teahouse – Chinese tea and handmade dumplings are winter tonics.

Lavender Bay to Kirribilli via Wendy Whiteley’s garden
For a secret garden and some of the best views of the city, trail down from Lavender Bay to Kirribilli. Start at North Sydney station and drop in at nearby Bay Ten Espresso for coffee and a hot bowl of soup to set you up. To find Wendy Whiteley’s Secret Garden, look out for the Harbourside Indian restaurant on Lavender Street and you’ll see a set of stairs that lead you there. The garden has been thriving for more than 20 years, and while it may not be the secret it once was, it’s still a sanctuary; with plants, flowers and trees of all shapes, sizes and colours and glimpses of the harbour below.

WILD IN THE CITY

Lane Cove National Park
Lane Cove National Park is a pocket of bushland that straddles Lane Cove River. It starts at East Ryde and winds up to Chatswood, Turramurra and Pennant Hills. Walks of various lengths, locations and topographies are mapped out here, ), but the two-and-a-half hour Fairyland loop track is a good place to start. Beginning at the corner of Delhi Road and River Avenue in Chatswood West, it follows a section of the Great North Walk and crosses through a defunct pleasure ground, Fairylands. Pleasure grounds were fashionable in Sydney in the late 19th century and this spot, accessed mostly by ferry, was once populated with a wharf, dance hall, kiosk and playground. After, drive to find roti at Mamak, dumplings at Tim Ho Wan or specialty coffee and freshly baked cakes at Lid & Jar.

nationalparks.nsw.gov.au

Vaucluse Coastal Walk and Cafe
Coastal air on a wintery day is invigorating. Fuel yourself with breakfast from The Trail – pulled pork and kimchi baked eggs or buckwheat-quinoa porridge perhaps – and grab a takeaway coffee for the road. Head for the Gothic-revival style estate of Vaucluse House for a snoop before joining the Hermitage Foreshore Scenic Walk at Nielsen Park. This hour-long trail to Bayview Hill Road in Rose Bay will take you through patches of rainforest and bush, slivers of sand and the grounds of Strickland House, with views of the Harbour Bridge and Shark Island.

nationalparks.nsw.gov.au

Crater Cove
Do you know about the tiny Mary Celeste-style settlement perched on the cliffs beneath Sydney’s suburban north shore? If you’re in the market for an adventure, here it is. Halfway into the Spit Bridge to Manly walk (down a well-worn but unmarked track beneath Grotto Point Reserve) lies Crater Cove. A small community of people lived here until they were forced to move in the mid-‘80s, occupying seven hand-fashioned shacks that still cling to the cliff-side. Built by fishermen between 1923 and 1963 and lived in from the ‘70s, these shacks still contain signs of a (simple) life. Clothing, cooking utensils and even a guitar are visible by peering through the windows. Visit on a weekend and you might be lucky – while there’s no schedule, the huts are sometimes open to the public.

FURTHER AFIELD

Jerusalem Bay Track
This five-hour bushwalk is easy to get to and from – simply hop on the train to Cowan and return from Brooklyn – but covers an impressive section of the Great North Walk through the Ku-ring-gai National Park. Scenery ranges from foreshore to ridge-top lookouts and the descent into Brooklyn offers beautiful views of the Hawkesbury River. Pack food, but stop off at the Angler’s Rest Hotel and Restaurant for a well-earned beer and a fresh fish dinner before catching the train back to Sydney.

nationalparks.nsw.gov.au

Bundeena
Bundeena is located in the expansive Royal National Park, which is also Australia’s oldest, that stretches away from Sydney’s south. An afternoon spent here will incorporate beaches, cliff tops and tracks through bushland and forest. If you visit on the first Sunday of each month you’ll also discover the community’s art trail, with local artists opening up their studios to visitors.

Just over an hour from Sydney, it’s easily accessible by car or by ferry from Cronulla, where you can start and finish your bushwalk with a nutritious breakfast and coffee from Mint Organics and a dinner from Queen Margherita of Savoy; one of Sydney’s best pizzerias (so says the city of Naples).

bundeenainfo.com

Helensburgh Tunnels

On the other side of the Royal National Park lies the town of Helensburgh, more than halfway to Wollongong. If you’re driving down the coast and need a place to stretch your legs, take some time to explore the abandoned railway tunnels buried deep in the bush. The Helensburgh and Metropolitan tunnels are located near Helensburgh station and are a masterstroke of human folly: built too small for steam trains to pass through without asphyxiating their passengers, they were closed not long after opening. German photographer Elger Esser captured this curiosity as part of a photographic journal he produced on New South Wales.

Updated June 5.