Bootlegger Cocktail Bar & Cuisine is described as a cozy, vintage speakeasy with warm lighting, tasteful decor, and live jazz that makes for a standout atmosphere; reviews praise creative, well balanced cocktails made with fresh ingredients, a strong whiskey selection, and an oyster focus that many find excellent, especially during happy hour; food earns praise for some dishes and vegetarian options, while a few entries note variability in quality and portion size and occasional kitchen misfires; the staff are repeatedly cited as friendly, attentive, and knowledgeable, with many guests appreciating personalized recommendations, though some experiences mention slow or uneven service and wait times or noise that can be a drawback for a quiet date; overall the venue is seen as a special spot for drinks, oysters, and live music, offering a memorable vibe and top tier cocktails that keep guests returning, while noting that prices can be high and consistency sometimes wavers.
Everything was perfect. From the helpful, attentive, patient staff, to the incredible, speakeasy-like atmosphere, to the live jazz band, to one of the best old-fashions I've had in my life. The burger was cooked to perfection, the spinach salad was seasoned & garnished BEAUTIFULLY, the fries were more like seasoned potato wedges. Easy to miss on the street, but an absolute home-run of an establishment that is not to be missed on a trip to the city. Upscale, expensive, but what you get is easily worth the price. Love that it's hard to find because it feels like secret knowledge for such an immaculate place. Even the walk up the stairs was neat.
C'est la 2e fois que nous venons passer la soirée au Bootlegger, nous sommes toujours ravis de notre expérience avec le concert de Jazz & la superbe ambiance !
Really enjoyed the Sunday night jazz + $1 oysters. Great venue, show, & the staff was top notch. Thanks to Remus for teaching me more about absinthe as he was expertly serving it to me. The host really went above & beyond as well, though I don't believe I caught his name. Highly recommend!
Had a great time here 😊 Paul was an excellent bartender & offered us some delicious cocktails. The live jazz was wonderful, definitely worth a try & definitely coming back!
Jan 12, 2026
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Nous sommes allés le dimanche pour la soirée Jazz, mais ce n'était pas vraiment du jazz qui jouait malheureusement…. On s'attendait à autre chose j'imagine saxophone, trompette etc. La nourriture était O.K par contre le plateau de charcuterie était incomplet il y a beaucoup de chose dans qui sont inscrits dans le menu, mais une fois le plateau arrive sur table il ne contenait que la viande froide une gelée de la moutarde & croûton. J'ai dû avertir la serveuse pour le reste qui nous a ramener un pot minuscule avec 3 olives 3 mini oignons perles & 3 morceaux de cornichon coupé en des……. Bref nous avons été déçue. Le service était bien au moins & l'endroit est très jolie beaucoup de potentiel.
There was a good live jazz show but otherwise expensive food & not good service. Our reserved table was not ready when we got there. The chicken burger seemed from frozen chicken strip, & the side salad was dry. Their cocktails are ok.
Ps. I already explained what needs improvement in the review. There's no need for me to email you. Read it.
I came in on a Wednesday night vibes were immaculate, got surprised by a jazz band,! i was welcomed by the LOVELY Rita sat at the bar in front of Tyler, made fantabulous drinks hit all the the tongue palates then Paul makes amazing creations. Just to mention RITA one more time, she's hilarious.
Drinks overpriced. Advertised as a jazz bar with live performances, there were no live performers nor jazz or blues music related to the theme of the bar. If you're willing to spend a lot on a night out, this is your place.. otherwise, there are options with better atmosphere, affordable food & drinks.
We ate here on a recent trip to Montreal. My wife likes to keep busy & she knows I like jazz so we just took a shot on this place. The jazz trio was fantastic. Ask for Remi. He helped us with our drink orders all night & was very helpful & informative.
Dec 8, 2025
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Première fois & certainement pas la dernière! Accueil très chaleureux à l'entrée!
Au bar, Tyler a rendu notre expérience mémorable! Il a très bien pris soin de nous. Il était à l'écoute, n'hésitait pas à répondre à nos questions, prenait le temps de nous expliquer certaines choses & très professionnel. Il nous a concocté de délicieux cocktails personnalisés aussi beaux que bons. Le groupe de Jazz a très bien performé ce dimanche. Belle découverte!
Wonderful experience, live jazz sessions on sundays, food was great. They have a variety of items to choose from for all of your cravings. Service was quick & efficient, the experience with the cocktails is a must! I would recommend this place 100%!
Superbe expérience au Bar Bootlegger 🍸! Cocktails originaux & plats délicieux ! Très belle ambiance avec concert de jazz & merci à Steven pour son accueil & Emy & Anaïs pour le service !
