The best things to do in Windsor

With its close neighbour Prahran, Windsor is an unmissable suburb of Melbourne. It was even ranked 10th in the list of the coolest neighbourhoods in the world established by Time Out magazine in September 2024! With countless op-shops, cafes, bars and restaurants lined along Chapel Street, it is for sure one of the liveliest. It’s also an area for which I have a particular attachment: this is where I lived during my first stay in Melbourne in 2016. It is therefore with an expert eye that I will help you discover all the best things to do in Windsor and Prahran!

One of the coolest neighbourhoods in the world

Summary

The 10th coolest neighbourhood in the world
Chapel Street
Street art in Windsor and Prahran
Eat, drink and party around Windsor
Getting there

The 10th coolest neighbourhood in the world

This is a list established each year by Time Out magazine: the “coolest neighbourhoods in the world”, whatever that really means. And in September 2024, Windsor, an inner suburb in the south of Melbourne, made it to the top 10! This list has obviously no real objective value (Brunswick in the north side of Melbourne was ranked 6th in 2023), but it is at least very accurate on one aspect: Windsor is worth a visit.

Windsor, but also its neighbour Prahran. In the same way as Fitzroy and Collingwood on the north side, these two suburbs are inseparable and share the same qualities... and the same issues. They both are a melting pot of people and have a real working-class atmosphere, with several second hand or antique shops, and a lot of graffiti and street art. You will find the same countless bars, restaurants, cafes in both, but also sadly the same homeless people and drug addicts, quite numerous in this part of Melbourne. All this is concentrated around one main artery: Chapel Street.

Chapel Street

From the banks of the Yarra River to the north to its intersection with Brighton Road to the south, Chapel Street passes through or goes along five neighbourhoods: South Yarra, Prahran, Windsor, St Kilda, St Kilda East and Balaclava. It is undoubtedly one of the liveliest streets in Melbourne. Alternately a shopping precinct, a temple of nightlife, or in some places a quiet residential area, it takes on several distinct personalities depending on where you are. The mix of architectural styles along it is also fascinating. On the Windsor side, it is lined with one-storey houses, with colourful facades and sometimes beautifully decorated pediments. Arriving on Prahran, the buildings rise in a disparate assortment of genres: the massive colonnades of Revolver, the Victorian architecture of the Town Hall or the gorgeous Prahran Arcade, my favourite building on Chapel Street.

Just across Dandenong Road on the St Kilda side, the large red brick facade of the Astor Theatre can also be seen from afar, with its huge, slightly dated sign framed by two rows of stars. It’s one of the most beautiful cinemas in Melbourne, and its programming combines blockbusters (I went to see Oppenheimer there for example) and arthouse movies.

The Prahran Market is just a stone’s throw away from Chapel Street on Commercial Road, which marks the boundary between Prahran and Windsor. Created in 1864, it is the oldest continuously running food market in Melbourne. It is open every Tuesday, Thursday, Friday, Saturday and Sunday.

Street art in Windsor and Prahran

As in many other places around Melbourne, there is a lot of street art in Windsor and Prahran. One of the laneways parallel to Chapel Street is even called ‘Artists Lane’, and its walls are entirely covered in paint!

See also: the best street art in Windsor and Prahran

My favourite murals in the area can be found on the Melbourne Polytechnic Building in Windsor. Four of its walls are painted: two on the north side by Reka One who represented native birds, one on the east side by Guido Van Helten (a portrait of the dancer Ana Seymour), and the last one on the west side by Sofles, with its characteristic style mixing drawing, graphic elements and tags.

Two other stunning artworks adorn the walls of Chapel Street, just before the intersection with Dandenong Road. On the left, above the railway tracks, Lynch painted the portrait of Australian basketball player Ben Simmons (sadly slightly defaced). On the right, the facade of Elfie Cafe, which opened in early 2024, has been decorated with a gorgeous mural by Marty Brazell.

Finally, one of the icons of Prahran is undoubtedly this giant robot painted by the British artist Phlegm that overlooks Chapel Street, close to the intersection with Commercial Road/Malvern Road. I love it!

Eat, drink and party around Windsor

The Chapel Street precinct between Windsor and Prahran is full of good addresses. It's impossible to list them all here, but here are some of my favourites!

For brunch, I can recommend either Babble Café on the corner of Prahran Square (I like their seatings overlooking the outside, allowing you to observe the activity on the street while enjoying your smashed avo), or Yellow Bird on Chapel Street. It also transforms into a bar in the evening with excellent beers. Don't miss the weekly 'Tijuana Tuesday' deals: delicious tacos at reduced prices and happy hour for drinks!

As for restaurants, the area also has no shortage of options. Lasagnes lovers, don't miss Lasagnalab on High Street. Generous plates, ideal to share! Still on Chapel Street, Henrietta offers excellent Middle Eastern dishes, revisited with an Australian twist. Slightly more expensive, but really delicious. Don’t forget to book! Hawker Hall is almost opposite it, on the other side of Chapel Street. This vast restaurant specialising in Asian cuisine offers a wide selection of dumplings, curries or noodles.

The choice is even wider when it comes to go for a drink! Slightly hidden on Wilson Street in South Yarra a little further north, Leonards House of Love is one of my favourite places in the area. I like the slightly punk atmosphere, and the offbeat look of the staff! Radical change of style at Jungle Boy on Chapel Street. Behind the innocent-looking facade of a sandwich shop, push the door of what seems to be the cold room and enter the tropical design of this secret bar! Cocktails are not cheap but really tasty, especially the famous Zombie.

To party until late at night, I recommend Lucky Coq, on the corner between Chapel and High Street. This is where I used to go out every weekend back in 2016, and it’s still one of my favourite clubs today! Entrance is free, and the atmosphere is always great. Finally, it’s impossible not to mention the Revolver Upstairs. I’m not a big fan of this club, famous for its excesses of all kinds, but it’s one of the icons of Melbourne’s night life. This is where you need to go if you’re after a huge night out: Rev’s is open non-stop from Saturday night to Monday morning!

Getting there

Windsor and Prahran are particularly well served by public transport. The two suburbs each have their own train station, on the Sandringham line. Tram 78 runs back and forth all day on Chapel Street, between Richmond and Balaclava. To/from the CBD, you can choose between tram 72 on Commercial Road/Malvern Road (which then continues towards Campberwell), tram 6 on High Street (towards Glen Iris), or trams 5 and 64 on Dandenong Road (which then serve Malvern and East Brighton respectively).

What are the best things to do in Windsor in your opinion? Do you think it deserves to be ranked amongst the coolest neighbourhood in the world? Send me a message to let me know!