The Owl Shop

Great choice of a cigar from the guy behind the bar. Also had Old Weller bourbon… is a Buffalo Trace product so I had to try it. Very smooth and tasty!
Great vibe here, cool people, great service.

As I’m writing this review, the remnants of stale cigarette smoke and perfume from last night are still permeated in my hair, and these wafts of olfactory delights invigorate nostalgic memories of my early twenties.
Smoking and drinking really do complement one another in a romantic way, and this place keeps that magic alive.
Color me sold.

Top notch joint. I enjoy a nice cigar now and then, and this place delivers atmosphere in spades. I’d recomend grabbing a comfy couch, a small lady like cigar, and a dark and stormy. Feeling classy.

You know the place has a certain charm about it if it draws an eclectic crowd.
It’s half bar, half cigar lounge, so expect to walk into a room filled with stumbling conversation smoothed out by a calming smokey ambiance.
The service was polite and the prices were standard.
I would definitely come back here, as it’s a great spot for feeling more suave than you actually are.

Solid spot for a night out with the boys. Owl Shop has plenty of whiskey and plenty of tobacco products.
I suppose if tobacco smoke in any of its various forms bothers you, this probably isn’t your place. But hell, if tobacco smoke bothers you don’t go to a smoke shop! Amirite?
Enough of my nonsense. Owl Shop has a great laid back and relaxed atmosphere for a night out. My friends and I especially like to hit this place up on nights when we don’t feel like a loud and crowded bar scene. Comfortable, intimate seating options and a dimly lit atmosphere make this place ideal for conversation that drifts off into the night just like the smoke rings being blown by the guy at the corner of the bar.
I could see it being a solid, creative date spot. It makes you feel like you stepped into a film noir where romance and intrigue are around every corner.

What a special place… I need to write before the memory fades and the music lingers softly and lightly in my head forever. I grew up in New Haven and am so very disappointed I knew not of this special space throughout my earlier years in college. Now I live in Lake Tahoe, California but return to the East Coast on occasion. I heard about The Owl Shop as I searched for live music during my upcoming visit. Anders Osborne was doing an acoustic night, something not to be missed… in a cigar shop! I bought the tickets in early June in the afternoon as I sat along the sunny shore of Lake Tahoe … a.k.a. «Lake of the Sky».
Soon after, I arrived to the shores of Milford, CT for family, fun and all the goodness it brings. I eagerly awaited the night of my visit to New Haven and live music with my beautiful, dear friend Ambroshia. It was a rainy night with blustery winds but we were ready for anything.
We walk in and the doorman (later known to me as Tiny) couldn’t find my name on the list. He was cordial and sweet. Eventually the big boss says «let them in» … (we were literally already in as the place is somewhat small and the music and tobacco scents waft mystically around the entire space… and what a beautiful space it is).
Unfortunately Bro and I are short, so by the time we got closer to the music it was standing room only and we couldn’t see. But we could certainly hear the beautiful sounds and lyrics from the effervescent Anders. and the vibe was pure, crystalline magic.
As the night progressed we found ourselves elsewhere (not because of me ;-) but I knew The Owl Shop was by far the classiest spot in town. Tiny became my favorite new friend. I’m not sure how he got that name because he has a big, beautiful heart. He reminded me of why I love and understand East Coast vibes. He was gentlemanly and warm as we waited, then offered us drinks and shared a cigar and stories with me as the night progressed. I felt like a princess queen. I was reminded again why my heart returns to the East and feels so at home in a place where long ago I felt so alone. Thank you for a beautiful night Tiny, Owl Club, and New Haven. Thank you for the magic of music (my true church)… I look forward to my next visit.

cool spot to read/​edit and have a drink in relaxed environment. but be prepared to stink like cigar smoke… assumed risk, not a big deal.
FYI: only knock — no beer on tap, but plenty o’ whiskey…

Fantastic selection of whiskey.
Awesome cigar selection.
Reasonably priced.
Very roomy and comfortable.
This place is awesome!!!

The Owl Shop has a selection of whiskeys that rivals some of the best bar establishments in New Haven. The ambiance is relaxed, dimly-​lit and perfect for an intimate night out. It’s lounge-​style so lots of couches and leather backed chairs. If you’re into whiskey, cigars, and places that exude history, you should check this place out.

If u like cigar, dim light and small conversations with random people this is the spot. They have great selections on everything and the people there are a character.

Best Mocha I have ever had in my life. This means a lot coming from a former barista.

I guess this is a weird review for me to write seeing as I don’t smoke. However, the service was great as was the ambiance. I really enjoyed my time there and the bartenders were great! It has a classic vibe to it (I could see a novelist writing a book in there). I went last week on a beautiful afternoon and they had the door open. It was excellent.

What a great little place. Went with my girlfriend on a Saturday evening after grabbing some pizza at Pepe’s. Got there around 10pm and a band was just wrapping up. We were able to grab some nice leather wingback chairs then moved onto the couch in the back. So comfortable all around. The staff was super friend and helped pick out a nice cigar that went with my drink as I am far from a expert. Also ordered Dark Chocolate coffee w/​sambuca. This was the most delishious coffee I’ve ever drank, bar none.

Wow, what an experience! Good cigar bars are few and far between these days, but the Owl Shop has it all. Ambiance, a wide selection of whiskies, coffees, teas, and most importantly cigars! The staff is super friendly attentive and helpful and the prices are very good — at least on the sticks!
Been there once, will be back often.

This place has a great 1920s-​1960s vibe to it. Basically get ready to strap yourself into a time machine, then sit back and enjoy your night. There is a full bar, the seats are comfy and large and you can just sit back and smoke away.
The cigars are excellent all around, some are reasonably priced, and they go all the way up to quite expensive ones. You also are allowed to bring in outside cigars/​cigarettes and so on.
The owl shop also appeals to a really wide array of patrons, while not falling too much into one category. Hipsters are there, yet it doesn’t feel like a hipster bar. Older gentleman are there, yet people in their 20s will feel quite comfortable and at home. You can sit at the bar and smoke a cigarette while watching sports, but yet if you’re only a mere 10 feet away it can feel like an intimate date. It really is rare that it’s able to strike this balance, but somehow it has captured that balance beautifully.
Wednesdays the Owl Shop also hosts jazz night, where various local jazz groups come in and play. The last time I went the group was quite talented, put on a great performance and was a treat to see. This further adds to the speak easy feel, that the bar is able to cultivate.
The Owl Shop also has great service. There is always a girl coming around offering to clear your ash tray, serve drinks or cut your cigar. They really pamper you and it is nice to see such strong service.
This is one of the most unique, most relaxing, and most intimate bars in Connecticut. This place should be on every Nutmegger’s bucket list, because it’s absolutely one of the jewels of Connecticut.

Miss the days when you could smoke in bars or even just smell a freshly lit cigar, i truly do. Its what made a bar unique and have a little character.
Thing is, Owl is in such a tight packed room and everyone is dragging like it’s a race to catch emphysema. It’s smoke overkill. One. place flat-​out stinks. Can’t enjoy your own Macanudo without inhaling 10 other peoples’ smoke. Two. need to dry clean clothes next day due to tobacco resin.
I’m 100% for letting smoking back into bars, but have the proper ventilation and size. Smoking should be allowed as an occasional, soothing release with your cocktail… not some chain puffing clowns in a box on furlough.

The Owl Shop tends to announce its presence forcefully with the aromas of leather, cedar, and spices lazily wafting over College Street. Once you step inside, ephemeral clouds of grey smoke slowly disperse to reveal dark wooden paneling, leather chairs and sofas, weighty ashtrays, and glass display cases featuring a vast array of cigars. An elegant ambiance. To forestall the inevitable question, yes, you will in all likelihood depart smelling like you just finished a week-​long bender with Don Draper circa Seasons 1 – 3. But that’s what showers and washing machines are for.
I’m hardly a smoker – half a cigar is usually more than enough to leave me feeling a little woozy. Bourbon, on the other hand, is a favored poison, and the selection of whiskeys at the Owl Shop is one of the best in New Haven. The servers are friendly and always happy to offer their opinions on the merits of various choices. For the sake of your lungs I wouldn’t advise going every night, but for a relaxed evening with a touch of sophistication, it’s hard to beat.

I love the Owl Shop. When I’m in downtown New Haven for any reason and have time for a nice little night cap, the Owl Shop is a must-​stop. I don’t even mind when I leave smelling like cigar smoke — it’s always a good time.
The atmosphere is really cool with dark wood and sweet leather couches and seats. I’ve been here for live music on certain weeknights and also on quieter weekend afternoons. Even when it gets crowded, the Owl Shop maintains a relaxed vibe. I love that you can smoke inside, and no matter what kind of cigar or cigarette you prefer, the Owl Shop is likely to have it as well as something you might like to try. They have a great selection of bourbon and whiskey, plus an expansive menu of coffee drinks. Beer selection is a little limited with nothing on tap, but you can always find a good beverage to enjoy with your cigar or cigarettes of choice.

Do you like feeling like you are helping out Al Capone in the 1920’s? Good me too
Atmosphere is awesome here very relaxed and calm. They have an awesome amount of dark and light liquor and a huge selection of cigars. If you dont mind smoke or if you do smoke cigars (or cigarettes) this place is great. The smoke doesnt build up either, because of the awesome ventilation.
This place is great for a meet up with a couple of close friends. When they have live music its the best.
I recently went to a burlesque show and then immediatly following that i came to the owl shop. Im living my dream out as a 1920s gangster.
And they have Pappy Van Winkle which is just absurd if you enjoy bourbon.

Oh Maaannn! I desperately want to love this place because the vibe is so chill. This is the adult equivalent of the cool kids’ table back in junior high.
Everyone is super interesting, the bartenders are friendly and lighthearted, and the dim lighting makes everyone appear incredibly good looking (okay, maybe a few drinks help too). On Tuesday and Wednesday nights they have live jazz bands which are off the chain.
Perfect, right? WRONG! The major malfunction is the crazy plumes of smoke I inhale. We have a fabulous time every time we go, but my lungs secretly hate me for it. Then, I think of how terrible a death from pulmonary carcinoma might be. Darn you tipsy thoughts!
I know, I know… wah wah wah… poor little baby is worried about her lungs. If this was the cool kids’ table, I would have been kicked off. Oh well. Pass me an oxygen tank, because there is nothing like this place in New Haven, and I wanna sit with the cool kids. So there.