The Best Things to Do in Sydney & New South Wales This Autumn-Winter Season

When you think of New South Wales’ capital city, it’s often the sail-like curves of the Sydney Opera House or Bondi Beach’s golden shoreline that come to mind. While these iconic landmarks are a must-visit, the region also offers a refreshing change of pace for those seeking seasonal charm—especially during autumn (March to May) and winter (June to August).

From cosy stays in heritage towns to spectacular festivals that light up the city, Sydney and its surroundings offer a variety of activities that come to life during the cooler months. With countless destinations just a short drive away, exploring is as easy as it is rewarding

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Not convinced yet? Here are nine things to do in Sydney and beyond for the ultimate seasonal adventure.

1. EXPERIENCE BRIGHT LIGHTS AND IMMERSIVE ART AT VIVID SYDNEY

From 23 May to 14 June, Sydney trades chilly nights for electric skies during Vivid Sydney, Australia’s largest festival. Iconic landmarks like the Sydney Opera House and the Sydney Harbour Bridge transform into glowing canvases for 3D light projections.

Wander through interactive installations, catch live music performances, join thought-provoking talks, or follow the scent of street food through buzzing precincts. Whether you’re with family, friends, or a date, Vivid Sydney turns the iconic harbour into a luminous playground that sparks wonder at every turn.

2. STROLL THROUGH THE COLOURFUL STREETS OF LEURA

Tucked in the Blue Mountains just a 90-minute drive or a two-hour train ride from Sydney, the quaint town of Leura transforms into a vibrant canvas during autumn. Tree-lined streets are shaded by maples and liquidambars, casting warm colours over the town’s charming cafés and boutique shops. At the edge of town, the heritage-listed Everglades House & Gardens offers a peaceful retreat. Stroll past its Art Deco house for high tea, take in sweeping views of the Jamison Valley, and wander garden paths scattered with autumn leaves. It’s the ideal spot for those who appreciate nature, design, and history.

3. RIDE THE SCENIC RAILWAY AT SCENIC WORLD

Looking to experience the Blue Mountains from a new perspective? Head to Scenic World, a family-owned gem established in 1945. Take a thrilling ride on the world’s steepest passenger railway, descending 310 meters into the lush rainforest at a dramatic 52-degree incline. For an added sense of adventure, hop on the Scenic Skyway, which offers breathtaking views of Katoomba Falls and the iconic Three Sisters. If you’re seeking an adrenaline rush, the Beyond Skyway lets you climb onto the roof of the Skyway for an unforgettable sunset view, complete with a celebratory champagne toast.

4. STARGAZE UNDER THE CLEAR SKIES

With lower humidity and cooler temperatures, autumn and winter nights are perfect for stargazing. At Wentworth Falls, Blue Mountains Stargazing offers small-group sessions led by expert astronomers. Guests can view planets, constellations, and other celestial objects through high-powered telescopes while learning the stories behind them. If the skies are cloudy, visit the pop-up planetarium, where you can stay warm and learn about the stars from the comfort of an inflatable bubble.

5. GO TRUFFLE HUNTING IN OBERON

Just a 2.5-hour drive from Sydney, Oberon invites you to a one-of-a-kind activity: truffle hunting. At RedGround, the region’s only truffière producing four culinary varieties, visitors can join guided hunts led by trained dogs in search of the prized black truffle. The adventure begins with an informative talk on truffle cultivation, followed by the hunt itself. Afterward, guests can indulge in truffle-infused gourmet bites paired with sparkling wine. With its scenic countryside setting, Oberon offers the perfect backdrop for farm-to-table culture.

6. EXPLORE GARDEN PATHS AND CELLAR DOORS IN THE SOUTHERN HIGHLANDS

Less than a two-hour drive from Sydney, the charming towns of Bowral and Berrima in the Southern Highlands offer the perfect escape during the cooler months. Spend your day sipping cool-climate wines at boutique cellar doors, exploring the stylish shops and cafés lining Bowral’s main street, or visiting Ngununggula, the region’s first major regional art gallery housed in a beautifully restored dairy.

If your trip extends into September, be sure to visit the Tulip Time Festival in Bowral—one of Australia’s oldest flower festivals—where thousands of tulips fill Corbett Gardens with vibrant colour from 12 September to 6 October 2025. You can also look forward to market stalls, art installations, live music, and roaming performers.

Then, make your way to the Bowral Honey Farm at Redford Park for a free honey tasting at their weekend stall and watch the beehives from a safe distance. For a hands-on experience, grab a ticket for their honey farm tour where you’ll get up close to the hives and sample up to eight honey varieties.

Berrima, just a short drive from Bowral, is equally charming with its historic feel and scenic beauty. While in Berrima, stop by PepperGreen Estate for a wine tasting from their vineyard, or take part in a premium olive oil tasting session for a true taste of the region’s local produce.

7. WATCH HUMPBACK WHALES MAKE A SPLASH

From May to November, thousands of humpback whales migrate along the New South Wales coast on the famed Humpback Highway. Sydney’s clifftop lookouts and whale-watching cruises from Circular Quay offer excellent vantage points to catch the action. Further north, Port Stephens is another hotspot, with sightings common at Fisherman’s Bay and Boat Harbour in Tomaree National Park. Down south, Jervis Bay’s calm waters make it an ideal spot for watching these gentle giants from shore. Keep an eye out—not just for humpbacks, but also for orcas, blue whales, minkes, and even sperm whales!

8. HIT THE SLOPES IN THE SNOWY MOUNTAINS (JUNE TO AUGUST)

Whether you’re skiing, snowboarding, or strolling along snow-covered trails, there’s something for everyone in the Snowy Mountains. Thredbo is home to Australia’s longest ski run and a scenic alpine village with cosy lodges, while Perisher—Australia’s largest ski resort—boasts four interconnected ski areas and over 1,200 hectares of terrain. For non-skiers, a scenic ride on Thredbo’s Kosciuszko Express Chairlift reveals sweeping views of Mt Kosciuszko, the country’s highest peak. After a day in the snow, relax by a fire with a hot drink or dig into hearty alpine fare at local restaurants.

9. BROWSE YOUR WAY THROUGH HAY ST MARKET AT PADDY’S

Newly opened in 2025, Hay St Market at Paddy’s is a vibrant market hub in the heart of Sydney that blends heritage charm with modern style. Just a stone’s throw from Chinatown, this revitalised marketplace boasts over 40 food stalls offering more than 25 international cuisines, alongside local designers selling unique handmade goods.

With live entertainment lighting up the weekends and extended hours every day, it’s the perfect place to indulge in global flavours, discover artisanal treasures, and experience the city’s buzzing energy.

So, what are you waiting for? Book your trip to Sydney and New South Wales here.

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