Your Ultimate Guide to the Month-Long Party Taking Over Greenwood Hotel

Grab your pals—particularly those who are single and ready to mingle—because The Greenwood Hotel is being transformed into Monkey Shoulder House for five weeks of organised frivolity. 

Kicking off in October, this residency will be stacked with music, movies, dancing, and dating, offering more excuses to catch up IRL than you can shake a Ginger Monkey at. With support from Monkey Shoulder, the takeover is bringing a next-level run of parties, pop-ups and playful moments designed to pull Sydney’s social pioneers together under one roof.

Here’s some of what you can expect. 

Whisky Cinema Club

Every Wednesday night from 1 to 29 October, The Greenwood’s Northern Courtyard will morph into an open-air cinema, complete with cult classics, whisky-infused popcorn and a Ginger Monkey cocktail in hand. 

The Whisky Cinema Club gives patrons a chance to kick back under the stars with loved ones and enjoy a film with a refreshing highball. Name a more dreamy combo, we’ll wait. 

THE DETAILS

What: Whisky Cinema Club
When: Wednesday night, 1, 8, 15, 22, 29 October
Where: Northern Courtyard, The Greenwood Hotel
Cost: Cinema is free, $10 for popcorn and drink
For more information, head here.

The Ultimate Dating Diaries 

Sydney singles, and the friends who know them best, this one’s for you. Monkey Shoulder and Thursday dating are teaming up to give you three ultimate IRL dating experiences.

Pitch Your Mate Night

A night of laughs, love, and chaos. This is your chance to grab your most single mates, pitch them on stage, and tell the crowd why they’d make the ultimate catch—expect hilarity, heartbreak, and some questionable reasoning.

Then watch the live dating show unfold. Think four eligible guys, one blindfolded woman, and plenty of audience-driven comedy. Cancel any post-show fans, because you'll want to stay after to swap stories, enjoy a drink in the beer garden, and maybe even meet someone new. Because honestly, dating is way more fun IRL—and a whole lot easier with friends by your side.

THE DETAILS

What: Pitch Your Single Friend
When: Thursday 9 Oct
Where:  The Greenwood Hotel
Cost: $20
For more information, head here.

Sunday Is For The Singles 

All of Sydney singles, one place one afternoon: no swiping, no pressure, just good vibes. Ease into your Sunday with a relaxed cocktail-style event made for connection, laughter and meeting new people in real life.

THE DETAILS

What: Sunday Funday
When: Sunday 26 Oct
Where:  The Greenwood Hotel
Cost: $20
For more information, head here.

Halloween: Dating Edition

To close out the series with the ultimate Halloween singles party. Think flirty costumers, spooky vibes, and enough energy to raise the spirits.  Sip on cocktails, wear your best disguise and get ready for the kind of night where sparks fly between trick or treat. Whether you’re a ghoster, a witch, or just here for a killer good time, one thing’s for sure: everyone’s single.

THE DETAILS

What: Halloween Party
When: Friday 31 Oct
Where:  The Greenwood Hotel
Cost: $20
For more information, head here.

HURRICANE: The Australian Luke Combs Tribute & The Country Allstars

Country fans are in for a treat with Hurricane, the Australian Luke Combs tribute band bringing all the anthems for one big Friday night of full-throated sing-alongs. If you’re lucky, the setlist might even include some Dolly Parton and Shania Twain classics.  

The energy continues every Tuesday with free line dancing classes, where instructors will guide you through the moves while the DJ spins honky-tonk classics. Keep yourself fuelled with $18 schnitties, $20 parmas, and a zingy Ginger Monkey on the side. 

THE DETAILS

What: HURRICANE & The Country Allstars + Line Dancing
When: Hurricane: Friday, 3 October; Line Dancing: Tuesday nights, 7, 14, 21, 28 October
Where: North Courtyard, The Greenwood Hotel
Cost: Hurricane: $38.40; Line Dancing: Free
For more information, head here.

Never Ending 80s 

It’s not a party until someone breaks out the synths, and the Never Ending 80s crew are bringing them in spades. 

The band is famous for their high-octane throwbacks, covering Madonna, Prince, Bon Jovi and all the icons that made the decade so influential. Lean into the theme with neon outfits, big hair and the kind of dance floor chaos only an 80’s soundtrack can inspire. 

The night will likely inspire you to whip out your E.T. VHS and crash in a dusty beanbag. 

THE DETAILS

What: Never Ending 80s
When: 8:30-11:30pm, Saturday, 11 October
Where: The Greenwood Hotel
Cost: $38.40
For more information, head here.

Tuesday Trivia  

Because everyone loves a little bit of trivia, on Tuesdays throughout October, The Greenwood will become the ultimate playground for brains and thumbs alike. Take on curated trivia challenges, chase high scores in classic arcade games, and test your reflexes alongside fellow competitors for the ultimate night of fun, laughter, and a little friendly rivalry. The best part you ask? It’s completely free. 

THE DETAILS

When: Every Tuesday in October
Where: The Greenwood Hotel
Cost: Free
For more information, head here.

Visit the Greenwood Hotel this month to enjoy all things good times, great events and a superior selection of sips. For more on why you need to head to Monkey Shoulder House for your next sipping session, visit here.

Editor's note: This article was produced in partnership with Monkey Shoulder. Thank you for supporting the partners who make Urban List possible. To read our editorial policy, click here.

Images: Supplied.