Ultimate Rocks Pub Crawl +Map: Self-Guided Tour of Sydney’s Oldest Pubs

Discover the hidden history of Sydney’s oldest neighbourhood, one pint at a time. This self-guided pub crawl through The Rocks offers a unique blend of history and good times. From convict-era watering holes to modern craft beer havens, you’ll experience a taste of Sydney’s past with every sip. Choose your own adventure – explore all twelve of these pubs, or create a shorter crawl to suit your pace.

This guide will help you navigate The Rocks’ pub scene, whether you’re a history enthusiast, a craft beer lover, or simply looking for a fun night out.

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Updated February 8, 2025: While we have updated this content today some details, including opening hours, prices and events, may have changed when you read this. It’s always a good idea to check the pub’s website or social media for the latest information.

History of Pubs in The Rocks in Sydney

The Rocks, Sydney’s oldest European settlement, has always been a hub for thirsty travelers and locals alike. Its pubs, rich in history, offer a glimpse into the lives of convicts, sailors and merchants who shaped the city’s early days.

The Rocks once boasted a pub on nearly every corner. While many were lost to time (and the 1900 bubonic plague outbreak), a dozen still stand, each with its own unique story to tell.

Imagine bustling pubs filled with sailors, merchants and former convicts – that was The Rocks in its heyday. These remaining establishments offer a link to Sydney’s vibrant past.

This guide focuses on the historic pubs, each a treasure trove of stories waiting to be explored.

Before we hit the pubs, let’s address a few important questions:

Why are bars in Australia called pubs?

Before the 1830s, anyone could sell drinks from their home. With the introduction of licensing laws, these establishments became known as “public houses,” required to offer accommodation and meals as well as drinks.

Aussies, being fond of abbreviations, shortened “public house” to “pub.” The “hotel” in many names reflects the original lodging requirement.

Which is the oldest pub in the Rocks?

The title of “oldest pub” is a friendly debate among several Rocks establishments. Each has a compelling story, adding to the intrigue of this historic neighbourhood.

As you explore The Rocks, consider the evidence and decide for yourself which pub deserves the title!

• The Lord Nelson: Claims the title of oldest continuously licensed pub, operating in the same location since 1841. Offers historic ales brewed on-site.
• The Fortune of War: Licensed since 1830, though existing in some form since 1823. A popular Anzac Day gathering spot. Although it had existed in some form since 1823, it closed for renovation for a while in the 1920s before it continued trading on the same site.
• The Australian Hotel originally on George Street as early as 1824, but moved to its current location in 1900. Now boasts a vast selection of Australian craft beers.

Now, let’s plan your Rocks pub crawl adventure!

The Rocks Pub Crawl Route

This pub crawl takes you on a winding journey through The Rocks, starting with the lively Fortune of War and ending at the historic Lord Nelson. The route is designed to be walkable, with estimated walking times between each stop.

Feel free to adjust the order or skip some based on your interests and stamina.

Stop 1: The Fortune of War (137 George St)

• Why it’s special: A local favorite and Anzac Day hotspot, with a lively atmosphere and regular live music. Claims to be the oldest pub in The Rocks, licensed since 1830.
• Must-try: the Marinated Olives and Hummus is a good way make sure you don’t head off on an empty tummy! Check their menu for more options.
• Atmosphere: Welcoming, historic.
• Estimated time to next stop: 2 minutes.

Stop 2: The Orient Hotel (87-89 George Street)

• Why it’s special: A Rocks landmark with a grand Victorian facade and live music seven days a week.
• Must-try: Cocktails and share plates at Mrs. Jones terrace bar, or a classic pub meal in the downstairs bar. (Check their current menu for the latest offerings.)
• Atmosphere: Lively, historic, with a touch of elegance.
• Estimated time to next stop: 1 minute.

Stop 3: The Observer Hotel (69 George Street)

• Why it’s special: A stunning example of Art Nouveau architecture. Sadly closed at the moment, but worth admiring from the outside.
• Estimated time to next stop: 1 minute.

Stop 4: The Mercantile Hotel (25 George St)

• Why it’s special: Australia’s (self-proclaimed) oldest Irish pub, with a cozy atmosphere, live Irish music, and a great selection of Irish beers and food.
• Must-try: A pint of Guinness and some traditional Irish stew.
• Atmosphere: Warm, friendly, a bit of craic.
• Estimated time to next stop: 3 minutes.

Stop 5: Harbour View Hotel (18 Lower Fort St)

• Why it’s special: A beautifully restored pub with stunning rooftop views of the Harbour Bridge, plus bridge memorabilia and a cocktail bar.
• Must-try: A cocktail on the rooftop with a view of the bridge.
• Atmosphere: Stylish, modern, with a touch of history.
• Estimated time to next stop: 5 minutes.

Stop 6: Hero of Waterloo (81 Lower Fort Street)

• Why it’s special: A historic pub with a fascinating (and slightly spooky) past, featuring hidden tunnels and convict cells. Live music on weekends.
• Must-try: Ask the staff about the history and see if they’ll show you the cells!
• Atmosphere: Historic, atmospheric, a bit of a hidden treasure.
• Estimated time to next stop: 2 minutes.

Stop 7: Glenmore Hotel (96-98 Cumberland Street)

• Why it’s special: A classic Aussie pub with a popular rooftop bar offering excellent views of the Opera House.
• Must-try: A cold beer on the rooftop while enjoying the view of the Opera House.
• Atmosphere: Lively, friendly, a good mix of locals and tourists.
• Estimated time to next stop: 5 minutes.

Stop 8: Australian Heritage Hotel (100 Cumberland St)

• Why it’s special: A celebration of Australian beer, with over 140 craft brews from around the country – they even have a beer passport!
• Must-try: Sample the coat of arms pizza – half emu & half pepper kangaroo!
• Atmosphere: Lively, patriotic, a great place to taste new brews.
• Estimated time to next stop: 7 minutes.

Stop 9: Lord Nelson (19 Kent St)

• Why it’s special: Australia’s oldest continually licensed pub brewery, with historic ales brewed on-site. A great conclusion to your historical pub crawl!
• Must-try: A sampler paddle of their house-brewed ales and the grilled halloumi cobb salad.
• Atmosphere: Historic, cozy, a genuine taste of old Sydney.

Still Thirsty? Try these Optional Extras

• Hotel Palisade (35 Bettington St): A stylishly restored pub with a rooftop bar offering harbour views.
• Captain Cook Hotel (33-35 Kent St): A classic local pub with a friendly atmosphere and good pub grub.
• Harts Pub (Corner of Essex & Gloucester Streets): A craft beer haven with a rotating selection of local brews.

Now that you’ve got your route, get ready to explore The Rocks’ pub scene. Each has a story to tell, from hidden tunnels to convict cells, adding a layer of intrigue to your pub crawl adventure.

A History of The Rocks, One Pub at a Time

The Fortune of War: Anzac Day Hotspot

Built in 1828 by Samuel Terry, a former convict who arrived in Sydney with nothing but a sentence for stealing stockings, the Fortune of War is a reflection of the resilience and ambition of early settlers.

A popular Anzac Day gathering spot, the Fortune of War sees veterans congregate after the annual march. If you’re in Sydney on Anzac Day, join the crowds for a tribute and a taste of Aussie camaraderie.

It’s also popular with locals being the closest pub to the ferry wharves, ideal for last-minute drinks.

Enjoy casual dining on the street or head to the “Lock Up” for a more upscale meal.

Where: 137 George St, The Rocks
When: 9 am till midnight most days (can be later on weekends)
More info: Check their website for the menu and what’s on the calendar

Orient Hotel – Victorian Grandeur

The Orient Hotel, housed in a grand Victorian building built in 1844, boasts a rich history. Originally a butcher shop, it transitioned to a pub in 1851, going through several name changes (including the Marine Hotel) before becoming the Orient in 1884. The name itself evokes images of grand steamships and exotic travel, reflecting The Rocks’ maritime past.

From butcher shop to bustling pub, the Orient Hotel has witnessed centuries of Sydney’s history unfold. Its Victorian facade stands as a proud reminder of a past era when The Rocks was a hub of maritime trade and adventure. Step inside and you’ll find a blend of old-world charm and modern comforts, a perfect spot to soak up the atmosphere of this historic neighborhood.

Tip: Catch the latest sporting action on the ground floor screens.

Considered one of the Rocks landmarks, mainly due to size and position on the corner of two of the main thoroughfares, it is also a standout for offering live music seven days a week.

Where: 87-89 George Street
When: 10 am to 3.30 am Friday and Saturday and midnight weekdays
More info: Check the website for more details on events.

Observer Hotel – Art Nouveau Beauty

While now permanently closed, The Observer Hotel building, listed on the NSW Heritage Register, remains a striking example of Art Nouveau architecture and is well worth a quick stop on your pub crawl.

Originally opened as the Observer Tavern in 1844, the current building dates back to 1909. Its distinctive Art Nouveau facade, with its flowing lines, intricate ornamentation and stained-glass windows, is a testament to the architectural trends of the early 20th century. Take a moment to appreciate this beautiful piece of Sydney’s history, even if you can’t step inside for a pint.

Where: 69 George Street, The Rocks

The Mercantile Hotel: A Touch of Ireland

Currently closed for renovation until Oct 2025, trading at Four Doors Down until then.

The Mercantile, a Federation Free Style building opened in 1915, claims the title of Australia’s oldest Irish pub. Its tile work and gorgeous wooden bar are worth a visit once renovations are complete.

While the renovation is underway head to “4 Doors Down” which is literally four doors away for all the favourite Merc meals and drinks, including Shamrock Pies and creamy pints of Guinness.

Tip: Monday to Friday, 5-7pm: $10 Pints (Guinness / Stone & Wood / Superdry), $8 select wines, $12 Aperol Spritz

The pub has also been voted Australia’s best Irish pub twice. If you’re craving a Guinness, this is the place to go. They also serve Irish classics like Guinness pie, Irish stew and a full Irish breakfast. Live (mainly Irish) music features from Thursday to Sunday and reasonably priced meals make this a popular spot for locals and visitors alike.

Where: 25 George St The Rocks
When: 11 am to midnight on weekdays, 10 am opening on weekends.
More info: Check renovation updates here

Harbour View Hotel – Bridge views and Rooftop Breezes

Built in 1922, the Harbour View Hotel, an Inter-war Free Classical style building, quickly became a popular spot for workers on the Sydney Harbour Bridge and the city circle railway tunnels. Interestingly, an earlier Harbour View Hotel existed in the 1840s on the site of the current bridge pylon. It was demolished to make way for the bridge’s construction.

Today, the Harbour View Hotel offers stunning views of the Sydney Harbour Bridge from its rooftop bar, an ideal spot to appreciate this iconic landmark.

Tip: Tuesdays is steak and schitty specials for $22

The pub’s decor features plenty of bridge memorabilia, making it a must-visit for anyone interested in the bridge’s history. If you can’t afford a BridgeClimb on your visit, a cocktail with a view is a great alternative.

Bit of trivia – my favourite local 1980s film, Starstruck featured the Harbour View.

Where: 18 Lower Fort St, Dawes Point
When: 11 am- till late
More info: Check the website for menus and events.

The Hero of Waterloo – Convicts, Tunnels and Tall Tales

Built in 1844 by stonemason George Paton (who also constructed the nearby Garrison Church), the Hero of Waterloo takes its name from the Duke of Wellington’s famous victory.

The pub’s sandstone walls, rumored to be sourced from the Argyle Cut, have witnessed centuries of The Rocks’ history unfold. From its early days, the Hero was a popular haunt for soldiers from the Garrison Church and sailors from the nearby docks at Millers Point. This street is one of the most beautiful in the area.

Beneath the pub lies a network of tunnels, rumored to have been used for smuggling rum – and perhaps even shanghaiing unsuspecting drunks! It is said that unwary patrons would be locked in basement cells overnight, only to wake up and find themselves press-ganged into service aboard a ship bound for distant lands.

Ask the friendly staff about the pub’s intriguing history – they might even show you the infamous cells!

These days, the Hero of Waterloo is known for its live music, a welcome sound in a neighborhood where quiet pubs are becoming increasingly rare. You can catch jazz, folk, soul and R&B performances, typically starting in the afternoon on weekends. It’s a great spot to relax after exploring The Rocks.

Where: 81 Lower Fort Street, The Rocks
When: Mon-Sat: 11am – 11pm and Sun: Noon – 10pm
More info: You can find more about the fascinating history of the Hero on their website.

Glenmore Hotel – Rooftop Views and Local Vibes

Built in 1921 by Tooth and Co. (Brewing), The Glenmore Hotel originally stood on the opposite side of the street. It was relocated brick by brick to its current location to make way for the southern approaches to the Sydney Harbour Bridge. Designed in the Inter-War Georgian Revival style, the building retains many original features, including fireplaces and ornate ceilings that were restored in 2016.

Today, the Glenmore is a classic Aussie pub with a lively atmosphere, especially on Thursday and Friday nights when locals gather to celebrate the end of the work week. Its rooftop bar is a major drawcard, offering spectacular views of the Sydney Opera House.

The Glenmore’s middle floor offers several smaller rooms, ideal for private parties or group gatherings. It’s also a popular NYE spot.

There are some good meal deals here mid week. Currently on offer are $12 burgers on Tuesday, $1 wings on Wednesdays and $20 steaks on Thursdays.

Where: 96-98 Cumberland Street, The Rocks
When: 11 am-midnight (1am on Fridays)
More info: Check the website for menu and event information

The Australian Heritage Hotel: A Celebration of Aussie Brews

The Australian Heritage Hotel, another contender for the title of “oldest pub in The Rocks,” has a fascinating history. Established in 1824 on George Street near the Museum of Contemporary Art, it was relocated to its current Cumberland Street address after the 1900 bubonic plague outbreak. This relocation contributes to the ongoing debate about the “oldest pub” title.

While some argue that moving to a new location disqualifies it, others maintain that its original establishment date should be the deciding factor. What do you think?

If you’re on a quest to sample the best of Australian beer, The Australian Heritage Hotel is an essential stop. These guys are passionate about Aussie brews, with an impressive selection of over 140 craft beers from around the country, including 20 on tap. They even offer a “beer passport” for those who want to document their journey through the world of Australian craft brewing.

Tip: For an authentic Aussie culinary experience, try the crocodile spring rolls or the iconic Coat of Arms pizza, featuring kangaroo and emu.

Experience another classic Aussie tradition – the Friday night pub meat raffle! It’s a fun and social way to support the local community and maybe even take home a prize. Tickets on sale from 5:30pm.

The Edwardian style architecture is in perfect condition, and the pub has kept most of its original design and fittings. Weekends are very popular, especially the outdoor seats that provide front-row views of the Harbour Bridge. If you fancy a really big night, you can book a room here.

Where: 100 Cumberland St, The Rocks
When: Mon-Sat: 11 am – 11 pm and Sun: Noon – 10pm (Verify and update.)
More info: Check their website for more information and follow them on social media (add links) for updates and events.

The Lord Nelson: Australia’s Oldest Pub Brewery

Built in 1836 by convict labor using sandstone from Observatory Hill, this historic building was originally the home of William Wells. He already operated a small pub nearby, converted his residence into a hotel and obtained a liquor license in 1841, establishing The Lord Nelson.

Remarkably, The Lord Nelson has been continuously operating as a pub ever since, earning its rightful claim as Australia’s oldest pub brewery.

As one of only three pubs to survive the bubonic plague outbreak of 1900 in Millers Point, The Lord Nelson stands as a testament to The Rocks’ resilience. Its rare Colonial Regency style adds to its historical significance and architectural beauty.

Beer enthusiasts will appreciate the on-site brewery, which produces six 100% natural ales without sugar or preservatives. From their historic ‘Three Sheets’ pale ale to their robust ‘Old Admiral’ porter, there’s a brew to suit every palate.

There is both bar food and a brassiere upstairs if you want something fancy. They also have rooms with ensuite or shared facilities from $220 a night—an excellent choice for anyone on a budget. Check here for details.

Where: 19 Kent Street The Rocks
When: Mon-Sat: 11 am – 11 pm and Sun: Noon – 10pm
More info: visit the website for details of the menu and brewery.

Hotel Palisade: History and Views

The Hotel Palisade, a five-story Federation freestyle building, has a rich history dating back to 1880 when a pub of the same name stood on this corner. The current structure, built by the Sydney Harbour Trust in 1915, was a popular spot for wharfies working in Walsh Bay and was known to be a good place to pick up some bargain goods ;-)

After being closed for seven years, the hotel underwent a $5 million restoration and reopened in 2015, combining historic charm with modern elegance.

The downstairs bar known as Public House has retained its original character and is a great spot to grab lunch after walking around Barangaroo Reserve. Prices are reasonable, with main course salads ranging from $18-20 and burgers at similar prices.

Tip: Happy Hour between 4-6pm Tuesday to Friday

Head up to the top floor to discover the Henry Deane, a stylish bar with breathtaking 360-degree views of Sydney Harbour. It’s a great spot to enjoy a sunset cocktail with friends, with share plates available to complement the stunning views.

If you are looking for a bed with a view, the rooms at the Palisades are lovely – check the photos here.

Where: 35 Bettington St, Millers Point
When: 12pm – 10pm, Sun, Tues. & Wed, 12pm-11pm Thurs and 12am on Fri-Sat. Closed Mondays.
More info: Check the hotel’s website for details of the various bars.

The Captain Cook Hotel: A Local Treasure in Millers Point

When The Captain Cook Hotel opened its doors in 1874, it was one of 18 pubs serving the thirsty residents of Millers Point. By 1928, only six of those remained, and today, just three originals survive: The Lord Nelson, The Hero of Waterloo and of course The Captain Cook.

This makes it a true survivor and a testament to the enduring spirit of the neighborhood. Step inside, and you’re likely to find yourself chatting with friendly locals, enjoying the authentic atmosphere of a Millers Point institution.

Local favorites like Young Henrys and Four Pines are usually on tap, showcasing Sydney’s vibrant craft beer scene.

The kitchen is open all day and serves a selection of burgers and other pub favorites. Local beers Young Henry’s and Hawkes Larger are on tap.

Open mic night every Thursday from 7 to 10 pm.

Tip: If you’re a local or planning an extended stay, check out the pub’s fishing club – a great way to connect with fellow anglers and experience Sydney Harbour from a different perspective.

Where: 33-35 Kent St Millers Point
When:Monday – Saturday: 8am – 11pm, Sunday: 8am – 9:30pm
More info: Check their website for events

Harts Pub: Craft Brews and Courtyard Vibes

Occupying what was once a grand private estate comprised of three two-story terraces, Harts Pub has a unique history. These buildings miraculously survived the demolitions that affected plague-ridden areas of The Rocks in 1900.

Harts boasts an impressive selection of craft beers, with 12 rotating taps showcasing the best of local and Australian breweries. You’ll always find a fresh and exciting range of brews to discover, from the crisp lagers of The Rocks Brewing Company.

Tuesday night trivia is always fun, and big sports events play on screens around the pub keeping local workers hanging about after work hours.

Tip: Happy hour Monday to Thursday 4.30pm-6.30pm and weekends 3:30pm-5:30pm

The menu features all the pub favourites along with a large selection of share plates.

Where: Corner of Essex & Gloucester Streets The Rocks
When: Sun-Wed: 12pm-12am, Thurs-Sat: 12pm-1am
More info: Check their website for deals and events.

Which Rocks pub is best for what?

Best pubs in the rocks for live Music

The Mercantile, The Orient or Fortune of War – all on George Street offer the best in live music.

The best pubs for drinking locally brewed Aussie beers

Australian Hotel, Lord Nelson and Harts have a good range of Aussie brews on tap and in bottles.

Pubs in the Rocks with a view

Glenmore Roof Top for views of the Opera House, The Harbour View for unbeatable Harbour Bridge Views and the Palisades for 360-degree water and city views with unbeatable sunsets.

Take a Rocks Pub Tour

If you like the idea of getting your general Rocks history with a side of beer, then one of these tours might be just what you are after. They are also great if you travel solo and don’t enjoy drinking alone.

The Rocks Pub Walk

This 2.5-hour walking tour will visit four heritage-listed pubs, including the haunted cellar at the Hero of Waterloo. Taste a local brew at each stop and hear stories of the people and places that will bring the Rocks to life.

The tour is offered three times a day and begins at Hart’s Pub. Get details and prices here.

Plan Your Own Rocks Pub Crawl Adventure

With its rich history and diverse selection of pubs, The Rocks offers a pub crawl experience unlike any other. Whether you’re a history buff, a craft beer enthusiast, or simply looking for a fun night out, you’re sure to find something to love in this historic neighborhood. Use this guide as a starting point, and don’t be afraid to explore and create your own unique Rocks pub crawl adventure. Cheers!

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