Best Cigar Shops & Lounges in Wallingford, CT

Best Cigar Shops & Lounges in Wallingford, CT

Whether you’re a seasoned connoisseur seeking a plush lounge with the perfect pour or a casual stogie aficionado who just wants a relaxing spot to puff with friends, I got you covered. Overall, there are many great options for cigars in Wallingford. Our top choice for best spot for cigars in Wallingford is Vanguard Cigar Club, but there are many to choose from.
Our list covers the top cigar havens in Wallingford, CT, catering to all walks of the cigar world. Fancy a place with top-shelf drinks and leather armchairs? We have it. Craving a chill hangout with a no-nonsense vibe? You bet. Looking to stock up on your favorite smokes, by the stick or the box? Yep, got that too. So, light up a metaphorical pre-amble cigar, settle in, and let’s explore the best cigar experiences Wallingford has to offer!

Top 3 Cigars Spots in Wallingford

1. Vanguard Cigar Club, 5/5
2. Up In Smoke, 5/5
3. the LUKE BRASSERIE, 4.8/5

Guide to Choosing a Cigar Lounge & Shop in Wallingford, CT

Choosing the right cigar spot in Wallingford isn’t just about the sticks, folks. There are many factors to consider for that perfect cigar sanctuary. First off, let’s talk budget. Are you rolling in dough, ready to drop some serious cash on fancy drinks and premium lounge memberships? Or you more of a kick-back-and-relax smoker on a budget?
What about selection? If you’re just looking for common cigars then most places will be ok, but if you’re looking for limited edition cigars or boutique brands, know that not every spot will have what you’re looking for.
Next up, lockers. If you’re a regular, having a personal humidor at the lounge is clutch – no more hauling your sticks around!
Then there’s the booze situation. Do they have a full bar with your favorite whiskeys, or are you stuck with a limited selection? Bonus points if you’re allowed to bring your own and not pay an opening or corking fee.
Finally, consider the vibe. Some spots get crazy crowded, while others have a mellow, laid-back feel.
Picking the right spot means matching your preferences and taking all these factors into account.

10 Best Cigars Lounges and Shops in Wallingford

1. Vanguard Cigar Club

Rating: 5/5
Phone: (203) 600-8783
Address: 803 W Main St Branford, CT 06405 United States
About: Specialities A premium cigar shop and top of the line smoking lounge dedicated to premium cigar selection and a sophisticated smoking environment. Upscale and comfortable furnishings with large screen tv’s and music, our lounge is unlike any other in the state! Offering day pass access as well as, memberships. Designed for both men and women who savor a great smoke and enjoy a VIP-like setting. Our lounge has been specifically designed to bring people together who share the passion for cigars and want to relax in an upscale setting that offers excellent ventilation, comfortable seating, expansive cigar selection. Bring your own food and beverage privileges. Check it out History Established in 2019. Family owned and operated. Meet the Business Owner Business owner information Ian F. Business Owner A passion for an old tradition of cigars runs in the family.

2. Up In Smoke

Rating: 5/5
Phone: (860) 632-1962
Address: 91 Berlin Rd Cromwell, CT 06416 United States
About: Specialities Up In Smoke provides fine handmade cigars and a smoking lounge for the most luxurious smoking experience. Strike a match and get to know us. Up in Smoke’s knowledgeable staff is ready to assist you throughout our clean, friendly and inviting floor that’s stocked with 1000’s of brand name cigars and a large selection of humidors, as well as premium Jamaican coffee. We have a walk-in humidor with a state-of-the-art reverse osmosis system. Our exclusive brand of cigars, Cigar of the Gods, are available in the store as well as online, and cigar-rolling event packages are available as well! We also offer outdoor accommodations featuring horse shoes, a golf chipping area and a quiet, private gathering space that is perfect for BYOB parties and events. The lounge includes bar tables with chairs, leather over-stuffed chairs and multiple TV’s. Did you know that you can also hire a cigar roller for your next event? We specialize in local events such as weddings and golf outings where you can “Lite” up with your friends and family. Give us a call or swing by sometime, our door is always open! History Established in 1996. Up In Smoke was created when Tony Tine was challenged in college to create a business plan for a fictitious company. He rose to the challenge and came up with a plan that sealed his fate. Upon graduating, he was asked by a relative to run his newly opened cigar shop. So after 6 months operating the shop, Tony realized his love for the cigar industry. He decided immediately to open his own shop, and on June 6, 1997, Up In Smoke opened its doors in Cromwell, CT. Meet the Business Owner Business owner information Tony T. Business Owner We would always smoke cigars after our football games in college and I did well in business class so I found a way to help others enjoy their smoking experience like I did. I’m thrilled to offer such a nice facility to fellow smokers with the stogies they actually look forward to toking on. Come on in anytime!


Rating: 4.8/5
Phone: (475) 666-8001
Address: 261 College St New Haven, CT 06510 United States
About: the LUKE BRASSERIE is your source for cigars in Wallingford. Visit the LUKE BRASSERIE’s website for more information about hours and selection.

4. Via Al Paraiso Bar & Grill

Rating: 4.5/5
Phone: (203) 725-3906
Address: 146 Grand St Waterbury, CT 06702 United States
About: Specialities Our restaurant is a family owned business. What makes us different is our unique food. We make food from our culture with love. Our latin flavors will have your taste buds dancing all around. We also make italian food. That comes from my cooking backround. Being a chef in NYC i learned alot of different flavors . come give us a try!

5. Wallingford Tobacco

Rating: 4.5/5
Phone: (203) 265-6099
Address: 898 N Colony Rd Wallingford, CT 06492 United States
About: Specialities We offer a wide variety of Premium Quality cigars kept in a huge state of the art walkin humidor. Cigar customrers can have access to our beautiful smoking lounge with nice leather couches and flat screen tv. We also carry wooden pipes, pipe tobacco, roll your own tobacco, electronic cigarettes, cigar accessories and much more. We sell cigarettes at state minimum price.

6. The Owl Shop

Rating: 4.5/5
Phone: (203) 624-3250
Address: 268 College St New Haven, CT 06510 United States
About: History Established in 1934. The Owl Shop was originally opened on Wall Street in 1934 by Joseph St. John who came to America from Greece in 1925. Beginning originally as a bookstore, he was also selling tobacco and mixing his own blends. In 1937, a second store on College Street was opened by Joseph and his wife Catherine, also of Greek descent. Expanding to having five stores they decided in 1951 to have everything under one roof, the College Street location. The Owl Shop is now owned by Glen Greenberg, who has owned the shop since November 1998. Today the shop still maintains its fine reputation for being one of the last, best, quality tobacco shops in the county offering a 400 sf walk in humidor, cigar lounge and bar, tobaccos blended on-premises, pipes, chess, backgammon sets and other fine gifts.

7. Total Wine & More

Rating: 4.1/5
Phone: (860) 313-1470
Address: 1451 New Britain Ave West Hartford, CT 06110 United States
About: Total Wine & More is your source for cigars in Wallingford. Visit Total Wine & More’s website for more information about hours and selection.

8. Westside Smoker’s II & Deli

Rating: 4/5
Phone: (203) 591-3040
Address: 112 Meriden Rd Waterbury, CT 06705 United States
About: Specialities We are a new smoke shop / restaurant/ convience store with a wide variety of products come here and get everything under one roof are goal is to make things easy for you

9. North of Havana Cigar and Lounge

Rating: 4/5
Phone: (203) 823-9760
Address: 77 State St North Haven, CT 06473 United States
About: Specialities A great selection of high quality cigar and tobacco products. Knowledgeable staff and a relaxing, clean, upscale, environment to enjoy. Ventilation and air quality is very important to us, as is the comfort of our non-smoking guests. We have worked very hard to make North of Havana friendly for our female clientele, and classy for couples and guests. You need not be a member to enjoy the lounge, flat screen TV’s, couches, chairs and conversation. History Established in 2012. The business opened officially on Saturday June 6th, 2012. The turnout was fantastic, the support amazing, and everyone had a great time. Meet the Business Owner Business owner information HR A. Business Owner Involved with cigars for around 10 years. I love a great glass of port, a strong coffee, or a nice dry red wine with a medium to full flavored cigar. I opened the lounge with my business partner because we saw a need in the community for an establishment that would provide a clean, refreshing, and relaxing environment for the consumption of cigars. We both love cigars and want to share our hobby with others. North of Havana Cigar and Lounge also recommends Joe’s Cigar Shop 1 Tobacconists HR A. says, “Joe’s has a great selection of cigars. The owner is very knowledgeable, and the shop is always spotless.”

10. Paradise Hills Vineyard & Winery

Rating: 4/5
Phone: (203) 284-0123
Address: 15 Windswept Hill Rd Wallingford, CT 06492 United States
About: Specialities Paradise Hills Vineyard is a Tuscan style tasting room, with its hand crafted copper bar, decorative chandeliers, and mahogany tables provide a romantic setting, to relax and enjoy the countryside with a fine glass of wine. History Established in 1997. Our story begins in 1997, when the Ruggiero family settled upon sixty-five acres of rolling hills and hay fields on Wind Swept Hill Road in Wallingford, Connecticut as the future home of Paradise Hills Vineyard and Winery. Planting its first vineyard that year, The Ruggiero’s witnessed the start of their lifelong dream to own and operate a family vineyard and winery. After fourteen years of operating solely as vineyard, supplying quality wine grapes to several Connecticut farm wineries, the Ruggiero’s are proud to open their new winery and tasting room for all to share some time in paradise. The intimate Tuscan styled room has a hand crafted copper bar, decorative chandelier, and mahogany tables which provide a romantic setting to enjoy the countryside. Come, relax and join us in Paradise. Meet the Business Owner Business owner information Margaret R. Business Owner There are four owners at Paradise Hills Vineyard & Winery: Margaret Ruggiero Natalie Ruggiero Brenda Ruggiero Albert Ruggiero Margaret Ruggiero is one of the owners and Primary Winemaker of Paradise Hills Vineyard & Winery. She is a graduate of the University of Connecticut and studied the field of Botany, Horticulture, Wildlife Conservation and Chemistry. After UConn Margaret pursued a Culinary Arts Degree to add a great fusion of food and wine making knowledge to her family business.

Basic Cigar Lounge Etiquette

Alright, so you’re ready to venture into a cigar lounge and be a respectable member of the smoky community. Here’s a quick rundown of some essential cigar lounge etiquette tips:
Cut and toast your own cigar. Most lounges provide tools, but don’t expect staff to do this for you. It’s part of the ritual!
Ask before lighting up next to someone. You might love the smell, but always be courteous to others.
Dispose of ashes and bands properly. Use the ashtrays, and keep the lounge clean.
Respect the cigars. Don’t handle other people’s smokes without permission, and avoid putting your mouth directly on someone else’s stick.
Mind your smoke. Try to direct smoke away from others. A breezy day calls for extra careful puffing!
Keep the noise down. Lounges are meant for relaxation and conversation, so try not to disrupt the vibe.
Tip the staff. Just like at a bar, tipping your servers is a sign of appreciation and good etiquette.
Don’t be afraid to ask questions. If you’re new to the scene, don’t hesitate! Most lounge regulars are happy to offer guidance.
Remember, a good cigar lounge is about enjoying your smokes in a welcoming and respectful environment.

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