We had a great night at the owl bar. Chadwick was our bartender and had all great suggestions for drinks and cigars. The prices aren't bad and the drinks were excellent. Highly recommended: THE LEGIONNAIRE $13 Vanilla Vodka, Pineapple Jalapeno Shrub, Dry Sherry, Lemon, Cassis - a F r e n c h M a r t i n i w i t h a t w i s t - The old school hip hop music was on and everyone seemed to be having a great night. There was no dress code and there was a mix of age levels. read more

This spot is rumored for having some of the best espresso martinis in downtown New Haven -- and I'd say they live up to the hype with a solid 7 out of 10. I was a little surprised that outside water bottles weren't allowed inside, especially on such a hot day, which definitely took away from the experience a bit. Also, if you're sensitive to the smell of smoke, you might want to skip this one -- it's pretty noticeable throughout the space. read more

The Owl Shop - Espresso martini - Tobacco Shops Near Me - New Haven, Connecticut

What a sweet cigar lounge with a great old school vibe. Opened in 1934 this place has a solid selection of cigars and whiskey. Prices are fair staff and patrons are cool. I had a Wiseman Maduro and a single barrel exclusive for The Owl. read more

The Owl Shop - Great vibe - Tobacco Shops Near Me - New Haven, Connecticut

Great place, great employees, great customers. It's the only place in town I can enjoy a good cup of coffee and a cigarette.

Yes it is the quintessential cigar shop and lounge. Full bar, any possible cigar you could want, excellent service! Has almost a speakeasy vibe. Been here several times, never disappointed read more

I love coming to the Owl Shop! I usually stop in every couple of months to meet up with a group fellow pipe smokers. We have had several meet ups here and each time, we all had a great time. I usually grab a couple of their "House Cigars" and a couple of Davidoff Cigars before I fire up a pipe. I like to have a nice cigar and a Redbreast Irish Whiskey, when I arrive. That has been my "Owl Shop Ritual" for every visit. I also grab a nice glass of Port, before I call it a day. Speaking of Whiskey, the Owl Shop has a very well stocked bar. A lot of Bourbons, but alas, not very many Irish Whiskey offerings. I'm sure they are sick of hearing me complain about their lack of "Irish", but they let me stay anyway! The lounge if very comfortable and there are several TVs playing throughout the location, if you are looking to catch a game that day. The crowd is mixed. Young, old, male , female. When Yale is in session, the place can get a little crowded with "Yalies". Some can be slightly obnoxious at times. I guess they are new to the concept of decorum within a cigar lounge / bar. Everyone has to learn and start somewhere, i guess. Having said that, I have never seen anyone "get out of hand". I know the Owner and Manager take absolutely zero crap from anyone who acts out. They run a very tight ship, indeed. The Owl Shop, is a great place to spend a Saturday afternoon and ponder world events while you enjoy your favorite cigar or pipe. A great place, run by very nice people. S.E.N. 02/19/2025 read more

A great place for a cigar and a drink. Friendly staff and good live music. Definitely recommend it.

While in New Haven visiting friends and family, we ended the night at The Owl Shop. They have great signature cocktails and tons of cigars to choose from. You can smoke inside which is obviously a rare sight to see nowadays. The ventilation system does a good job of clearing the smoke inside. They also have a bunch of tables and chairs out front for those who prefer outdoor seating. Friendly service and cool ambiance. Definitely worth checking out. Don't forget to grab a souvenir coaster or match box! read more

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This place always delivers! And a great place to just chill and have good cocktails. Staff is very pleasant and knowledgeable.

Moody vibes and great selection of smokables but the drinks were less than espresso-so... read more

The Owl Shop - Tobacco Shops Near Me - New Haven, Connecticut

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Had a pretty fun time here at the bar last night. All the tables were full so we just stood there having a few cocktails. I loved my El Presidente drink special, and the bartender was absolutely hilarious. I will have to come back to try a cigar next time, looked like they have some nice offerings. read more

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Such a chill place to get away and relax at. I had B-52 and a very tasty vanilla cigar. I'm no avid cigar smoker but seeing how 2020 was such an interesting year that I figured, why not? I must visit, for sure. read more

The Owl Shop - a hand holding a cigar - Tobacco Shops Near Me - New Haven, Connecticut

The best cigar bar so far in CT. Nothing like Club Mac in NYC or Davidoff RIP. The layout is this, the posers are more in the front of the bar, date nights in the middle- maybe posers as well not definitive; if you only have 1 cigar and one 1 drink undisputedly a poser. Back are the cigar aficionados; we are watching you and laughing in our silence. Great food for a cigar bar. Libations are vast and tandem with cigars. Definitely a place to go. read more

5 stars for you from my visits many, many, many years ago. Purchased wood carved figurines and some beautiful music boxes of which I still take very good care of. Just wondering if you still carry these types of items. Love you OWL SHOP! read more

My review might be considered useless and not the most helpful, but here it is anyway. I'm not a smoker, I don't ever smoke, yet I found myself in this cigar lounge. I was with a few people who wanted to smoke cigars on a nice afternoon in New Haven. We walked inside this place, I immediately had to step outside, the smell was nauseating, and so uncomfortable. They thankfully offer outdoor seating. I can't speak to the variety of cigars they offer because it's just not something that interests me, or that I know much about. The menu is chunky, with a strong odor of smoke, it has lots choose from, and it isn't food. They do offer a variety of cocktails, whisky and coffee. I had a nice cappuccino, that came well presented in proper dish ware, not the typical paper cups. I enjoyed this coffee, and the seating outside was appreciated, I had to turn at an angle to avoid smoke coming my way. Not a place I plan on returning to again personally, but if you're into cigars, it might be worthy of a visit. read more

The Owl Shop - Cappuccino - Tobacco Shops Near Me - New Haven, Connecticut

As long as I've been in New Haven, this is the second time I've been in Owl Shop and actually sat down (outside because that smoke is not getting in my hair) as a patron. Stopped by here on a Sunday Funday as my friends wanted to grab a cigar and drink. While I wasn't smoking, I did ask for a Side Car and the bartender actually made it right and it's not even on their menu. I was very impressed by that, along with how attentive the wait staff was. I wouldn't go here on a busy night but I certainly will on a Sunday evening. The vibe was perfect! read more

The Owl Shop - Tobacco Shops Near Me - New Haven, Connecticut

This review is based on sitting at the bar for a few hours and enjoying cocktails, not smoking a cigar. I plan to indulge in the excellent selection on my next visit. The bar staff were knowledgeable and friendly. The drink selection is vast and the specialties fit the decor and style. The space is anchored by a long bar but there are tables and comfortable seating throughout the place for relaxing and smoking. The draw here is the cigars, smoking the cigars inside, and drinks to have while smoking cigars inside (it delivers on all fronts). It is/was/will be smokey inside due to people smoking, so prepare to have to wash your clothes after a visit. The backstory/history is cool and the decor lives up to it. I very much plan on visiting again. read more

Nice place for a drink and to listen to cool Jazz. This place attracts a decent crowd of folks. Nice chill atmosphere. read more

The Owl Shop - Tobacco Shops Near Me - New Haven, Connecticut

The owl shop is one of the oldest bars in New Haven. This establishment brings a welcoming feel to newcomers and friendly greetings to regular patrons. While they offer a wide range of cigars and cigarettes, their options for drinks are also extensive and well made. I would suggest going for one of the jazz nights that they host weekly if you're looking for something relaxing and fun to do! read more

Went there in August no problems. 6 months later they recharged me after I deactived the card because of an issue on THEIR END. This caused an overdraft fee and many other issues. Absolutely unacceptable, 6 months later is crazy with no other authorization. Shady business doing sketchy stuff stay away or pay with cash. read more

Love it here. I don't smoke personally but my boyfriend does and I've tried some of the tobacco they have, it's smooth and goes light. Plus, Tuesdays and Wednesdays, live music for free! Their drinks are also amazing and their dirty martini is the way to go! Also the nutty Irishman is delicious! Staff is polite and very attentive. Love coming here! read more

I'm visiting with the band Portugal The Man doing a show next door I'm their truck driver. The crew guys told me about the Owl Shop and I just had to visit being a cigar and coffee guy and I was not disappointed!!! The ladies on staff were so welcoming and helpful and made me the best mocha latte!! Made my visit here perfect! My gratitude to them I'll be back at load out for another round!! If you love history and good coffee or bourbon and cigars it's a must visit in New Haven!! Sincerely, Greg read more

Great atmosphere and great music! Definitely an easy place to just relax. The beer was good.

Possibly my favorite cigar shop in the country. Great selection of cigars. Great service. Drinks and beautiful, fun people.

wouldnt sell us a loose cig. would have been way cooler if they did. ......xxxxxxxxxxxxxx.................... read more

The Owl Shop - found our own - Tobacco Shops Near Me - New Haven, Connecticut

If you haven't gone to Owl Shop and smoked a fat cigar with one of their signature cocktails, you haven't lived.

Was up in New Haven for a reunion and had a chance to stop by. Can't complain about a place where you can smoke a nice cigar and order a good drink. It seems these kinds of places are getting rarer. As to the place, it was quite spacious and on the night I was there not that crowded so ventilation was fine. The whisky selection was extensive. Cigar selection could have been a little better, but they had all the standards and were well humidified. read more

This place has one of the best old fashions I've ever had. And what a chill spot! Loved sitting outside, having a drink, and a delicious cigar. I was only inside for a very brief period of time, but it looked super cool on the inside too! Definitely recommend for hanging out and relaxing with friends. read more

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. read more

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This is the best hangout spot I've ever been to. Amanda is the best barista I've ever met. She is so sweet. She makes the best drinks. Ask for her when you come here. You will have the best time ever! Love her so much. Gina is also the best bartender. If you want good drinks, ask for her. Amazing! Best experience everytime you come here! read more

This surprised me. Think olde school speakeasy. The place was packed after work. Very impressed with the cigar selection and bar. Filled with fine whiskey, brandy and port wine. It has a coffee and sweet bar along with some impressive antipasto platters. There's live music late night and plenty of cigars to go around. Definitely a great after dinner stop. Come thru and enjoy. read more

The Owl Shop - Tobacco Shops Near Me - New Haven, Connecticut

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Cigars, scotch, and sports on TV. Really enjoyed getting away from the laws of CA. A true cigar bar! read more

The Owl Shop - Oban with a beer back - Tobacco Shops Near Me - New Haven, Connecticut

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A classic joint I have been frequenting for decades. Great selection, decent prices and a full bar with great coffee. What's not to like right? Parking in New Haven is predictably a challenge but that's why they make garages. When your tee time gets rained out on a summer Saturday there is one solution. The Owl Shop. read more

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Fantastic atmosphere with music, cigars and drinks. Staff was very accommodating. Whiskey selection was excellent. Highly recommend a visit.

Outstanding whiskey selection. Perfect for cigar lovers inside. Good music and great atmosphere.

Grab a unique cocktail and peruse the enormous (and constantly updating/changing) menu of cigars and sit down at a very classy spot. There is a very interesting cross section of people here. Some in shorts and a t-shirt just grabbing a cigar, some (like us) were slightly dressed up and just enjoying the end of a great bar crawl. A few are dressed to the 9's with top hats and wood-carved pipes. The wait staff was very knowledgeable about the cigar types, and the menus themselves explain styles and cuts. The best part is that there is little to no pretension here. Even if you are a cigar novice, you can have a good time. They could use a little more ventilation inside as it felt a little heady. Also a little more sitting room outside would be nice as everything was taken. But that just means it was busy which is always a good thing. read more

The Owl Shop - Tobacco Shops Near Me - New Haven, Connecticut

God I love this place. Where else can you sit down in a great atmosphere with a wonderful staff and enjoy a coffee with Baileys while enjoying a cigarette. read more

This is my favorite place in the city. There are amazing cigars and amazing drinks! Raina and Tessa make sure I get great drinks and have a wonderful time. Aygen makes sure I have a table and have amazing time. I've never had a bad time at owl shop. Can you go in for a cigar and old fashioned? Yes. Can you stop by for an espresso martini and a chill night? Yes. Can you ask for special cocktails and a smaller cigar? DEFINITELY YES! This place is a gem in the New Haven area! There's no where better to spend your time! I come here for date night, I come here for pre-dinner drinks, I come here for post-dinner drinks, I come here to study, I come here to relax. Owl Shop may be the best spot to spend time in New Haven regardless of why or how you made your way here. Trust me in this you will never be disappointed. My favorite place in the city!! read more

Great whiskey and bourbon selection, bartender was friendly and has great info on cigars and drinks

I'm not even a smoker and I love this place. Great spot to sit with a Manhattan and chat.