If you live in The Hills and haven’t made the trip out to Richmond and Windsor lately, it’s worth putting in the diary. We visited Richmond recently and it’s such a lovely change from city life: wide streets, old colonial buildings and none of the rush. Windsor, just down the road, has the same quiet charm. Together they make an easy, relaxed day trip that doesn’t need much planning.
Getting there
Both towns sit about 45 minutes to an hour from The Hills, depending on traffic, and you’ve got options for getting there. Driving is the simplest: Richmond and Windsor are only a few minutes apart from each other, so you can easily do both in one day. If you’d rather leave the car at home, you can also take the train; both towns sit on the same line, making it easy to hop between them.
Richmond: a heritage walk through colonial history
Richmond is one of five towns established in the Hawkesbury region back in 1810, and its history is easy to soak up on foot. The town’s compact, walkable layout is made for a self-guided heritage walk past old colonial buildings, quiet residential streets, and the market square that was first surveyed in 1811.
A few buildings worth slowing down for along the way:
- Bowman House, built between 1817 and 1820 on Windsor Street, is one of the town’s oldest surviving residences and now serves as the local Hawkesbury area office.
- Richmond Post Office, on Windsor Street, dates from the 1870s and 1880s and is one of the district’s grander heritage-listed public buildings, with a distinctive second-storey addition from 1888.
- St Peters Anglican Church, at the western end of Windsor Street, anchors one of the heritage walk precincts and is surrounded by buildings constructed during the first hundred years of European settlement.
The Hawkesbury Council offers free heritage walk booklets covering different precincts of the town; you can pick one up locally or download and print it before you go so you know exactly what you’re looking at as you wander.
When you’re ready for a break, Richmond has a good spread of cafés along Windsor Street. The Black Duck Espresso Café is a solid choice, as is Lil Miss Collins on Windsor St. If you’re feeling a bit more adventurous, it’s worth taking a five-minute detour to Hobartville to check out The Little Olive.
For a great pub lunch, get yourself to the historic Royal Richmond bistro. Go for the food, stay for the ambience.
For something more exotic, the local Thai boasts “We’re awesome” and the lunch special during the week is a very reasonable $16.
If you’re in Richmond on a Saturday, don’t miss the Richmond Good Food Market, on every Saturday morning at the cricket ground.
Windsor 2756: more heritage, more history
Windsor has a similar heritage walk, taking in the historic Windsor Mall precinct and its collection of colonial-era buildings, churches, and cottages. Like Richmond, it’s a compact town that rewards slow walking rather than rushing between sights.
The standout here is the Macquarie Arms Hotel, on the corner of George Street and Thompson Square. Built in 1815 on the orders of Governor Lachlan Macquarie, it’s recognised as the oldest surviving hotel building on the Australian mainland, and it’s still serving pub meals today, making it a fitting spot for lunch with a side of history. Thompson Square itself, one of the best-preserved Georgian town squares in the country, is worth a slow lap before or after.
While you’re there, it’s worth stopping in at the Hawkesbury Regional Gallery, located in the Deerubbin Centre on George Street. It’s free to enter and runs a changing program of exhibitions across visual art, craft, photography and design: a nice indoor pause if you need a break from walking, or shelter if the weather turns. The gallery’s own Evergreen Café is a pleasant spot for a coffee among the landscaped grounds, and Lime & Coconut Cafe nearby is well regarded for breakfast if you’re after something more substantial.
Windsor outdoor activities
When you’re tired of looking at historic buildings, take a picnic to a bank overlooking the Hawkesbury River or get in your steps and take the Windsor trail. This one- to two-hour family walk starts at The Terrace in Windsor, taking in river views from the viewing platform before heading north past the new Windsor Bridge to explore heritage signs and historic buildings around Thompson’s Square, including The Doctors House, the Macquarie Arms Hotel, and a flood marker. At the top of the square, a QR code offers a Welcome to Country video about the Darug people. The walk continues across the bridge (remarkably flooded in 2021 and 202) to a western viewing platform, then on to Macquarie Park for a playground, green space, and seafood lunch, finishing with a chance to dip your toes in the river’s edge (though swimming isn’t recommended due to strong currents).
Best time to go
Both towns sit in a rural setting, surrounded by farmland and the Hawkesbury River, which makes them especially pretty in spring. If you can time your trip for a clear spring day, the walk between colonial buildings and green paddocks is hard to beat.
The last word
A day trip to Richmond and Windsor is an easy way to swap city noise for a slower pace without a long drive. Grab a heritage walk booklet, wander both town centres taking in the old churches, post offices and Australia’s oldest pub, stop for a coffee or a pub lunch along the way, then duck into the gallery before you head home. It adds up to a full, but relaxed, day out.
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