A bar crawl down the Windsor-end of Chapel Street

It’s no secret that I love living in Melbourne’s inner-south suburb of Windsor, right on the doorstep of the best end of Chapel Street. In fact, I have so much oozing love for the teeny-sized suburb that I’m desperately saving my pennies, one cappuccino at a time, so I can afford the seven-figure price tag to buy in this area.

One of the things I love the most about Windsor is the amount of options there are to order an alcoholic beverage. New bars are always sprouting out of the pavement, making me feel like my own neighbourhood is as foreign as my mum speaking Mandarin.

So, last weekend I decided to explore the Windsor-end of Chapel Street, inch-by-inch, familiarising myself with (and, of course, documenting) every single bar, pub and drinking venue there is to find*. Starting on the western side of Chapel Street, at the Dandenong Road end (for which there was no real reason), here are all 22 venues, from R&B lounges and gyrating dance floors to footy-obsessed pubs and intimate wine bars. And just to qualify, they need to be more bar than bistro to have made this list.

* This is correct at the time this post was published. Going by how quick bars pop up on this stretch of road, it will no doubt be out of date by tomorrow morning.

Killing Time

I’ve walked/driven past this shanty town-type slither of a bar many times, but never paid it any attention. Perhaps because the electro music isn’t my taste, the beer garden is oddly decorated with stuffed gorillas and it appears to have raided Windsor’s hard rubbish collect day for its decor. Enter at your own risk.

11 Chapel Street, Windsor

Mother’s Milk

[CLOSED] Mother’s Milk is another slice of northside on the southside, but a little more within my district of comfort. It’s intimate and cosy, with worn leather couches, an ambient fireplace and some of the most delicious cocktails in the land.

17 Chapel Street, Windsor

The Railway Hotel

The Railway Hotel is like a Vietnamese roll; lots of ingredients all rolled up in one. Take your pick whether you keep it casual and hang out in the downstairs bar, join the Sunday sesh rooftop deck ritual, go full foodie in the formal Highline Restaurant, or don’t remove your Peter Alexanders and head straight for the 24-hour Thirsty Camel bottle-o.

29 Chapel Street, Windsor

Wonderland

With a healthy daily happy hour from 4–8pm, it might explain why this cocktail bar is always as packed as the Prahran Woolworths’ car park. Although there’s plenty of comfy lounge-style seating inside, I prefer the leafy curbside courtyard, listening to the trains go rumbling through Windsor Station, which is right next door.

37 Chapel Street, Windsor

Holy Grail

Decked out with a nautical theme, antiquities and ’70s chairs that have been whisked from my childhood home, the open front bar at Holy Grail falls away to intimate couch seating, where I prefer to hide away and make the most of the service bell. This is a relaxed place to enjoy a gin and juice.

67 Chapel Street, Windsor

Chapel Street Cellars

A wine aficionado’s candy store, this bottle-o-meets bar is the brainchild of a sommelier and wine educator couple, so expect some quality candy. If you can’t wait to get home with your purchased loot, perch yourself at one of the tasting tables and crack open your chosen bottle of wine, spirit, craft beer or cider, and capitalise on the BYO food policy.

89 Chapel Street, Windsor

Yukie’s Snack Bar

On any given night, Chapel Street institution Mr Miyagi has a big angry crowd waiting to wrap their lips around a nori taco. So it’s not surprising that they’ve given the masses a licensed alternative to wait in that’s not the park bench out the front of Foodworks. Accessed through the back of Mr M’s main dining space, Yukie’s Snack Bar is a vibey place (once the fresh paint smells dissipate) to enjoy a drink, admire some street art and eat a quick snack. Disappointingly, the famed nori tacos aren’t available from Yukie’s, so on exit I may have contemplated stealing the grilled salmon belly, sushi rice, spicy napa cabbage delicacy from a tray sitting unmanned on the kitchen counter…

99 Chapel Street, Windsor

Hoo Haa

With bangin’ beats, an outdoor courtyard and free entry, this is one of my favourite dance floors south of the river.

105 Chapel Street, Windsor

Lucky Liquor

This small hole-in-the-wall bar has cheapish drinks and a fun atmosphere, but borders on the boundary of dive. I’m also not sure I can get past the name, which sounds like it’s a bottle-o next to a brothel.

125 Chapel Street, Windsor

Morris Jones

Super popular with the fash pack, I don’t really understand the appeal of Morris Jones as a bar choice (the restaurant, different story). What’s enjoyable about lining up at the bar for 30 minutes, navigating your way through the four-deep crowd, then standing squished up against a stranger, Sandringham train line style, spilling your over-priced drink as you’re pushed by everyone else trying to find a non-claustrophobic mingle spot, all while trying to look like you’re super ok about this complete invasion of personal space?

163 Chapel Street, Windsor

Borsch, Vodka and Tears

Ok, this place is borderline more bar than bistro, but given I stopped here for a plate of vodkas and a plate of dumplings, I figured it made the list. Here you could easily fool yourself for thinking you’re in the middle of Warsaw, with soft candlelit lighting, ornate mirrors, eclectic wooden tables and chairs, page-after-page dedicated to exotic Eastern European vodkas and beers, hearty polish fare and communist-style bathrooms. There’s a reason it’s a Chapel Street bastion.

173 Chapel Street, Windsor

Lucky Coq

If you’re allergic to the colour red, back away because this place is dip-died in red hues. Part pub, part nightclub, Lucky Coq is a student and backpackers’ hideaway with a free pool table, dance floor, arcade games (not free), cheap pizza and cheap-tasting wines.

179 Chapel Street, Windsor

The Wolf and I

Back down the eastern side of Chapel Street, first stop is the big, imposing, grey monolith that used to be dive bar The Swan Hotel. As far removed from a dive bar as Kim Kardashian is from Kate Moss, The Wolf and I now still confusingly passes as a pub from the outside, but inside expect to find a modern fit-out, Scandinavian menu and a DJ playing Ice Cube’s You Can Do It.

152 Chapel Street, Windsor 

La La Land

Put those red goggles back on for this small lounge bar that skirts the boundary of student drop-in centre, with second-hand couches (perhaps from the nearby Salvos) that come complete with cigarette burns. The décor is completed by a confusing mix of a fan and fireplace, animal heads and hand-me-down lamps. The drinks list is equally hobbled together.

134 Chapel Street, Windsor

Yellow Bird

This brightly-coloured café-come-cocktail bar is a Chapel Street favourite, where you can drink beer out of a can and embrace a bit of rock’n’roll. Then come morning, if you wake up feeling like a small animal has died in your mouth, try the signature Death Benedict at this retro diner.

122 Chapel Street, Windsor

The Social

Just like Simon who sat in the front row of my Year 12 maths class, I was oblivious to The Social. And I was a little hesitant to acquaint myself, given the guard of men not-so-casually manning the front door, assessing every single Y chromosome that entered the venue. I wouldn’t have been surprised if they had a 10-scale system in use, just like the high school corridors. But then I remembered the rules of the game; every single bar I must document, standing on the pavement didn’t count. I did go inside, although can’t say I stayed that long, just long enough to assess the apparently-popular red colour scheme, a DJ whipping up a dance floor and the much older 40-something crowd that were very obviously on the prowl.

116 Chapel Street, Windsor

The Woods of Windsor

If Chapel Street Cellars is a wine lover’s paradise, The Woods of Windsor is a whiskey aficionado’s Bora Bora. Not just a lesson on the varying types of whiskeys, including single malts and blends, but also sophistication, with full table service, food pairings, dark wood décor and a swing soundtrack. Just don’t mind the taxidermy animals watching over.

108 Chapel Street, Windsor

Boston Sub and Jungle Boy

Boston Sub is definitely one of my favourite Barbies. This dimly-lit, jungle-like bar, that’s accessed through a freezer door, is a hipster’s wet dream. Sitting here in what could be someone’s tropical-themed outdoor courtyard you’re oblivious to the bustling goings-on beyond the freezer door as copious cocktails are poured in tiki mugs.

Read the blog post that re-enacts how I accidently discovered and fell in love with Boston Sub’s hidden cocktail bar.

96 Chapel Street, Windsor

The Union

Another big grey monolith on Chapel Street, but The Union is 100% pub inside and out, with true-to-form beer, sports and parmas flowing faster than the NBN.

90 Chapel Street, Windsor 

56 Bricks

This newish, two-level bar is tres cool, with Biggie and Bob Marley wall art, a happy hour that lasts five hours and a Step Up-style dance floor (minus Channing). The dress code is strictly Converse and caps.

56 Chapel Street, Windsor

Naked European

New to Windsor, this restaurant bar offers a paired back European foodie experience that could fool you for thinking you’re somewhere on the Mediteranean. Pop in late for a casual, low-key drink. 

50 Chapel Street, Windsor

Lady Nelson’s Wine + Kitchen

Given I drink wine like it’s water, the addition of a wine bar to Chapel Street brings me a bucket of happiness. With a hard-to-choose-from wine list, some of the friendliest staff on the strip and little snack-type nibblettes, Lady Nelson’s Wine + Kitchen is the perfect place for a girls catch-up.

44 Chapel Street, Windsor

So, what are my favourite Windsor bars?

There you have it, a dictionary on all 22 of the Chapel Street, Windsor, bars, covering off every possible type of theme and liquor, seeing multiple uses of the word ‘lucky’, enough red lights and tones to think we were at a Sydney Swans game, and, the best bit, no cover charges to be seen.

Admittedly, squeezing 22 bars into the one Saturday night is ambitious (although I challenge you to try!), so which ones should you prioritise? It depends on your preferred flavour of nightlife. Given I’m allergic to pubs and lounge bars, if I only had five roses to hand out, they’d go to Yukie’s Snack Bar; Hoo Haa; Boston Sub; Borsch, Vodka and Tears; and Lady Nelson’s Wine + Kitchen.