The Oldest Bar in Sydney: A Tale of Detectiving, Drinking, and Dungeons

food, restaurants, Sydney
Just call us the Bloodhound Gang of the Brewpubs.

College Friend and I found ourselves embroiled in a mystery that required a commitment to sleuthing … and drinking. In the end, we proved ourselves to be worthy at at least one of these professions.

Our mission, which we chose to accept, was to gather evidence as to which of three bars claiming to be Sydney’s oldest really was deserving of the title. Taking no shortcuts, we conducted our research by visiting each establishment as undercover officers of the alehound variety.

The Back Story: The Rocks is a fantastic neighborhood in Sydney, which today sits just West of the Opera House and directly in the shadows of the Sydney Harbour Bridge. It is home to the oldest buildings in the city. The sandstone row houses today host bars, cafes, tourist shops, and fancy apartments, but they remain aesthetically evocative of the rougher early days of Sydney. My romantic imagination summons images of British soldiers ruling over their convict wards and salty seamen roaming the cobblestone alleyways, teased by the calls of messy haired, rouged up prostitutes teetering teasingly over wrought iron balconies. It’s a rather cliche vision, but I like it, nonetheless.

The contenders for Oldest Bar are three: Fortune of War, Lord Nelson, and Hero of Waterloo. The controversy stems from a complicated history of continuous licenses, time in the buildings, name changes, and so forth. We inspected maps, deeds, journalistic accounts, and of course, sought the answer in a steady stream of half-pints.

The Findings

Contender #1: Fortune of War


The Claim: “The oldest continuously licensed public hotel in Sydney.”

The Evidence: Fortune of War has a distinct advantage at winning the hearts of Sydney tourists looking for the Oldest Bar because it is the only one of the three that is located on what you might call “the beaten path” of The Rocks neighborhood. They have a license that dates back to 1828, though College Friend and I were puzzled by this document hanging on the wall that seems to be dated 1814. The dispute comes from the fact that there have been several buildings on the site where Fortune of War stands, so the building is not actually the oldest.


The Environment: College Friend and I went in at about 5p.m. on a weekday, and there were just a handful of guests there. I understand that it can get quite busy at peak times. The main bar is a long, dark wood rectangle in the middle of the room. The walls are covered in old photos, news clippings, and some neat commercial maps of Sydney in the early 1800s. There is an adjoining room with “pokie” machines and bar tables. Purportedly, there is a great balcony outdoor space, but it was closed on the day we went.

Adventures Had: Next to none. A moderately disinterested/unfriendly Australian bar mistress took our orders for half pints (Toohey’s New for me. I can’t remember what College Friend had). We inspected the walls and rooms, as we sipped, and found ourselves thoroughly uninspired to stay any longer.

Conclusion: Fortune of War has a pretty darn good claim on this “Oldest Bar” thing; but, I can’t say I’ll be in a big hurry to go back. Nothin’ special today, from what I saw. I’d like to see the upstairs, but I’ll probably just leave it to the tourists.

Contender #2: Lord Nelson Hotel


The Claim: “Sydney’s Oldest Licensed Hotel.” (Hotels are synonymous with pubs in Australia)

The Evidence: Based on a liquor license issued in 1831, the site of current Lord Nelson had several names and owners from 1831 – 1841, when it got the current name. The building is original.

The Environment: A bustling bar, full of local professionals – women and men in dark business suits, one and all – and maybe a handful of tourists. The large main room features a dark wood bar, a lot of individual tables, and a fireplace. A second room on the main floor has a few tables and a glass window that shows off the Lord Nelson Brewery room. There is a nice restaurant upstairs.

Adventures Had: College Friend and I visited Lord Nelson’s twice (just for the sake of the investigation, mind you). Our first foray was on a Friday night. It was packed with casual locals and a rowdy Hen’s Night party upstairs. College Friend struck up a conversation with a couple of guys next to us, who turned out to be a soon-to-be American expat and his buddy. We drank a few of the resident brews until we were unceremoniously kicked out at 11p.m. (Lord Nelson and Hero of Waterloo both close early because they are in a residential neighborhood). We collected our new friends and Partner-in-Crime, and went down the road for a few more brewskies at The Mercantile Hotel, which dates to only 1914, so wholly out of the running for our pennant, but still a great night out with the fantastic Shaylee Wilde singing rock/country covers in a Aussie-accented Janis Joplin growl.

We went back to Lord Nelson right after our stop-off at the Fortune of War with one clear objective in mind (well, two objectives, of course – the first was the important business of sleuthing): The Ploughman’s plate.


We’d noticed a lot of people eating it on our previous visit, and felt compelled to try it. The slab contains copious pieces of beer damper (I had to look it up – I had no idea what kind of bread it was, but yowza was it delicious – sweet and rich), cheese, an egg, pickled cucumbers and onions, and little dobs of mustard and chutney. Between that and our two Lord Nelson brews, one plate was more than enough food to count as dinner for both of us. This British style pub food may well be growing on me. On the downside, the service was incredibly slow, the bartenders were moderately unpleasant, and the noise level was scream-at-your-neighbor high.

Conclusion: I could cast a vote for Lord Nelson as oldest bar, based on the age of the building (think of the ghost stories this place must have). Moreover, Lord Nelson brews some damn fine beer: We tried the Old Admiral strong ale (yum), Nelson’s Brew porter (two thumbs up), and the Three Sheets golden beer (light and fruity goodness). I’d go back in a heartbeat for the great beers (there are four kinds I haven’t tried yet), but definitely not during the after work rush.

Photobucket (A Three Sheets and Nelson’s Blood)

Contender #3: Hero of Waterloo


The Claim: While College Friend had read a book claiming that Hero of Waterloo was the oldest bar in Sydney, further investigation really doesn’t support that claim. Hero was built in 1843 out of a piece of sandstone from The Argyle Cut, a passage stairway between two nearby streets that is still there today.

The Evidence: Hero of Waterloo may have been eked out of the Oldest Bar running, but it definitely has the most colorful history. Its most interesting feature is the dungeon/cellar where drunken patrons were dropped into through trap doors, locked up, and then sold into service at sea. The tunnels and cellar were also used for rum running.

The Environment: The main room features a long bar (dark wood, as you’ve probably guessed), as well as a couple of tables, a small stage for live music, and a fireplace with a large drawing of Napoleon over the mantle. There’s a dining room off to the side with a few pokies, and some outdoor seating, as well. The clientèle seems to be mostly locals of the laid back non-rowdy variety.

Adventures Had: Even after we’d ruled Hero out of the running for Oldest Bar, it still warranted two visits – because we just liked it that much.

On our first visit, we tried a number of different Australian beers. I found an affection for all things James Squire. We also struck up a friendship with a couple of locals who worked at an ad agency nearby. Our hilarious cohorts entertained us with tales of their travels to Hogs N Heifers in NYC and kidded us about fulfilling our American stereotypes. My favorite line of the night was, “You confuse me. You’re American. But you’re polite. But you have a nose ring. …” College Friend and I really did do our best to be good ambassadors abroad.

Our bartender, young David, was simply the most amiable Irish bloke around. It took awhile, but we eventually talked him into slipping away from the bar for a minute to show us the dungeon. And there it was, in all its dark, dank, dungeony glory. I can’t say whether the shackles on the gates were authentic or merely nicely rusted out props for the tourists, but we were happy to fall for it.

Photobucket (College Friend’s arm in shackles)

We went back for our second trip to Hero after our Ploughman’s at Lord Nelson for our final drink of the night. David remembered us and seemed genuinely happy to see us. If there is anything that recommends a bar more than being remembered by the friendly bartender, I know not what it is. Compared to the raucous Lord Nelson, Hero was bustling but calm, and we were able to enjoy conversation over our pints without yelling at each other.

Conclusion: Oldest BarSchmoldest Bar. Hero of Waterloo is my favorite for as long as David is there to serve me, the crowd remains friendly and mild, and the dungeon lurks below.

Cheers, mate!

Next up in Tales from First Visitor: Adventures in Meat Pies

5 thoughts on “The Oldest Bar in Sydney: A Tale of Detectiving, Drinking, and Dungeons

  1. Mimi and Joe

    I loved this!! I was very interested when you mentioned it the other day so I was much looking forward to this post – it did not dissapoint.

    If you need someone to go back and try more of the Lord Nelson brews just let me know… I am an “avid” beer drinker 🙂

  2. C. In Oz

    Partner-in-Crime is not a beer drinker, so it might not be his scene, but he’s usually pretty game for whatever rolls his way. It would be fun to get them together! (Any luck on your crate, by the way? I’ve been crossing all my fingers for you!)

  3. Mimi and Joe

    Very funny – mine is not a beer drinker either; but he will have a drink in a bar so I guess they could get girlie drinks while we have our frosty delicious beers.

    They were supposed to call and schedule deliver yesterday; but that didn’t happen. Joe said that he will call them today and pin them down on a time.

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