While most Sydneysiders spend April battling the crowds at the Blue Mountains and the Southern Highlands for a glimpse of autumn colour, a far more peaceful — and colourful — alternative is perched quietly on the banks of the Hawkesbury River. Just a short train ride from the city, Windsor offers an easy escape that feels removed from the usual leaf-peeping circuit. At a time when filling up the tank is only getting more expensive, the historic town is one of the easiest day trips to do by public transport, with a charming town centre that is easy to explore on foot and pockets of autumn colour, particularly along its riverfront stretches and local parks. Here’s everything you can see, eat and do in Windsor this autumn.
Things to do in Windsor this autumn
Ideal for a spontaneous weekend trip, Windsor doesn’t require much planning. Established in 1810 under Governor Lachlan Macquarie, it’s one of the oldest colonial towns in Australia, with well-preserved architecture from the yesteryear and plenty of old-world charm to boot. Many of the buildings in town date back to the 19th century, with original churches, sandstone cottages, and civic spaces that still reflect their early colonial character.
Start your trip at Thompson Square, the oldest public square in Australia and one of the few civic spaces from the early colony that remains largely well preserved. Set beside the Hawkesbury River, the square is framed by a cluster of Georgian buildings, including the Macquarie Arms Hotel, which has been operating since 1815 and is widely recognised as the oldest mainland pub in the country. It’s worth grabbing a drink here and finding a seat on the veranda to soak up the vintage atmosphere before heading out again.
A few minutes from the square is St Matthew’s Anglican Church, a handsome brick building from 1817 and one of the oldest Anglican churches in Australia. You can also walk past the Windsor Court House or head to the Hawkesbury Regional Museum to see local colonial and Indigenous artefacts. If you’d rather just browse, George Street is the town’s main strip, with a handful of independent shops and antique stores that fit the historic feel of the area.
If you’re chasing autumn foliage, follow the path down to The Terrace and into Howe Park, where a flat walking track runs parallel to the riverbank. Parts of this stretch are lined with large deciduous trees that turn shades of bright gold and burnt orange, with a light carpet of leaves scattered along the trail during peak season. Beyond the riverbank, a notably vibrant display can be found along Hawkesbury Valley Way. This stretch of road connects Windsor to Richmond, and is lined with large London Plane trees that turn a consistent bronze and yellow as the leaves change.
If you have a car, the underrated Cattai National Park is a 15-minute drive away, and the area near the river and the main road into the campground is planted with maple and plane trees, which provide more variety in colour, including reds and dazzling yellows.
Other ways to enjoy the town
When you’re ready to eat, Windsor’s main streets offer plenty of stellar options for a bite. George St Loft and Lime & Coconut Cafe are popular options for a casual lunch or coffee, while the Church Bar offers woodfired pizzas and classic pub grub in a converted church building. Other local favourites include Cafe Cornerstone for brunch and coffee, Simon’s Cafe for a stacked all-day menu, The Second Home Cafe for vegan options and Outback Bakehouse for pies and sweet treats. For a proper meal, head to Cricca for modern Italian cuisine and cocktails.
If you’re visiting on a Sunday, the Windsor Mall Sunday Market takes over the main street with stalls selling local produce, handmade crafts, and vintage items. For more shopping, make your way to Manor on George for vintage and antique furniture or By a Farmers Daughter for homewares, fashion, gifts and more. Read more about Windsor and find accommodation options here.
Getting there
Windsor is located right outside Sydney, a short one-hour drive from the CBD via the M2 and M7 motorways. If you prefer public transport, direct trains run from Central to Windsor, with the journey roughly taking around 70 minutes. Once you arrive, the historic town centre and riverfront are a short walk from the platform, so you don’t need a car to explore the main sites. Plan your travels on Transport for NSW.
