7 Winter Day Trips from Sydney
- Smashd Sydney
- 6 days ago
- 4 min read
Updated: 19 hours ago
Sydney’s winters are mild, but just far enough from the city, the season feels sharper — colder air, slower days, and fewer crowds. It’s the best time to head out for a day: to walk, eat, wine taste, or just be somewhere else for a while.
This is a curated guide to six winter day trips from Sydney — from the highland towns of Bowral and Oberon to Megalong Valley vineyards, Shoalhaven wineries, and cold coastal walks in Port Stephens.
Winter Day Trips from Sydney
Blue Mountains
1.5 hours from Sydney
Known for its stunning views, eucalyptus forests, and federation-era towns, the Blue Mountains have long been Sydney’s go-to winter escape. The cooler air, misty trails, and slower pace make it well-suited to day trips built around walking, exploring, eating, or all three. Wander through the towns and take in the kookiness of Katoomba, the old-world charm of Leura, or the emerging art scene in Blackheath.
Start slow with breakfast at Glasshouse, or plan your day around a long lunch at Tempus or Ates, both serve thoughtful, seasonal food. Stop in for hot chocolate at Blue Mountains Chocolate Company, or try a local award winning beer at Mountain Culture.
From there, it’s up to you: hop along to various lookouts, visit a Japanese-style bath house, or a plan a proper hiking trails.
Bowral
1.5 hours from Sydney
Bowral is a small country town that punches above its weight, especially in winter. Start with coffee at Nick’s or crepes from Franquette, then wander through antiques at Dirty Jane’s and The Potting Shed for all things country garden, two local institutions sitting side by side.
Main Street is made for unhurried browsing, vintage coats, design-forward homewares, and one-off pieces you won’t find back in Sydney. For lunch, book a table at Harry’s on Green Lane, or if wine’s more your pace, stop in at Bendooley Estate for a tasting by the fire.
If the light holds, end the day with a drive up to Mount Gibraltar Lookout for a view over town.
Berry
2 hours from Sydney
A small town on the South Coast known for its food scene, boutique stores, and proximity to the Shoalhaven wine region. Queen Street is the main strip, home to a mix of cafés, bakeries, and design-led retail. Milkwood Bakery opens early and sells out fast—croissants, sourdough, and takeaway coffee are the focus. South on Albany offers a seasonal set menu in a quiet space just off the main street. Tre Bambini does house-made pasta and woodfired pizza, while Queen St Eatery leans more French-Australian with clean interiors and a regional wine list.
Nearby Wineries including Two Figs and The Silos Estate all offer tastings and food with views over the Shoalhaven.
Megalong Valley
2 hours from Sydney
Tucked below Blackheath, Megalong Valley feels like a quiet secret. The road in winds through bushland before opening into wide paddocks and soft, open sky. In winter, the light stays low and the valley holds onto the cold, in the best way.
Stop in at Megalong Valley Tea Rooms a cute cafe with outdoor tables overlooking alpacas in a field with old school scones with jam and cream (with homemade jam). Just a short drive down the road you can book a wine tasting at Dryridge Estate or Megalong Creek Estate, two small cellar doors with stunning views and even better wine.
If you're up for a walk, you can join the Six Foot Track for a short stretch.
Port Stephens
2.5 hours from Sydney
Winter is when Port Stephens slows down — and that’s exactly why it’s worth the trip. Think coastal walks, whale watching, and afternoons spent over wine or beer.
Start your day with breakfast at The Little Nel in Nelson Bay before tackling the Tomaree Head Summit Walk. It’s short but steep, with sweeping views over Shoal Bay and the coastline. Winter is the best time to see whales, book a whale-watching cruise or simply head to the cliffs at Fingal Bay or Boat Harbour for a good chance at spotting them from shore.
You can also ride the quad bikes across the sand dunes, try sandboarding, or take things slow with a stop at Murray’s Brewery for craft beer and woodfired pizza. If wine’s more your thing, Wonganella Estate is a cosy spot tucked into the trees for a glass and a view.
Hunter Valley
2.5 hours from Sydney
One of Australia’s most established wine regions, the Hunter Valley combines legacy estates with a new wave of independent producers. Long associated with Semillon and Shiraz, the region has quietly evolved, its cellar doors now spanning the traditional and the experimental, often within a short drive of each other.
At Iron Gate Estate, Mediterranean varietals are poured in a terracotta-toned space with a slower rhythm. Vinden Wines brings a more modern energy, led by a second-generation winemaker focused on small-batch blends. At the more established end, Tyrrell’s and Lindeman’s offer a sense of the region’s legacy, both worth visiting for their historic estates and classic styles.
For something quieter, Krinklewood serves biodynamic wines in a sandstone-framed courtyard surrounded by gardens. Before heading home, stop by the Hunter Valley Smelly Cheese Shop to pick up a few bottles and cheeses to match.
Oberon / Snow-Hunting
2.5 hours from Sydney
Located on the western edge of the Blue Mountains, Oberon is one of the few places near Sydney where snowfall is possible. When conditions are right, areas like Shooter’s Hill, Black Springs, and Mount Werong offer open access to pine-lined roads and quiet stretches of forest. It’s an easy day trip built around snow play, build a snowman, have a snowball fight, and spend a few hours in the cold.
Live snow cams track local conditions and make it easy to plan the drive.
Nearby, Mayfield Garden remains open through winter. Designed across expansive grounds, the garden’s formal hedges, stone paths and structured plantings are particularly striking in the colder months, with a café on-site serving hot food and drinks throughout the season.
Looking for more things to do in Sydney?
Comments