Señor Cigars: A Sweet Spot in Ocean City, Maryland

Since 1977, Señor Cigars has been the signature cigar destination of Ocean City, Maryland, a major beach resort area along the East Coast. Founded by Bruce and Carolyn Kennington, the enterprise consists of two separate locations, featuring a world-class selection of premium hand-rolled cigars topped off with the very best in personalized service.

The Kenningtons entered the cigar trade in the 1970s while running kiosks at a mall in Columbia, Maryland. Bruce says: “We accidentally got into the business because Carolyn was talking to mall management. They were thinking about opening a cigar shop and Carolyn jumped on the opportunity.” 

The couple ultimately opened a small storefront in Ocean City before expanding to the 33rd Street Plaza in 2014. In recent years, the Kenningtons have eased away from the day-to-day management of Señor Cigars, letting their manager, Barry Mederrick, take over. 

Mederrick, who started with the company back in 2012, manages both shops. He brings a distinctive skill set, having spent 16 years overseas doing contract work for the government as well as working on local economies in five different countries and running the duty-free operation for the United Nations peacekeeping force in Israel. 

According to Mederrick: “While I lived overseas all those years, I just got into cigars, had a passion for them. That’s my background. When I was in charge of the duty-free operations we had predominantly Cubans. I started to read and learn about the product. I made myself aware of what was going on, following things in the industry.”

Regarding his passion, like so many of us, Mederrick finds smoking a cigar “an event,” a special time to unwind and relax when you sit down for a little bit of time to yourself, some peace and quiet. He says, “Just to enjoy a cigar and think about what you’re doing takes away all your cares and troubles—it’s just an awesome experience.”

Ocean City is a seasonal environment, a beach town that supports a year-round population of about 7,000 and approximately 8 million visitors annually. People start coming to fish in April if the weather’s right, while others take advantage of golf packages. 

“We really have four months to make our money to pay expenses for the whole year,” Mederrick explains. “Now, we have two shops and stay open all year. So, we may close one of the shops down in January for one day and then one shop on the other day. There’s always a shop open, and other than Christmas, we’re open every day of the year.”

Their seating capacity is 12 at the 33rd Street location and 20 at the 118th Street shop with 11 employees, including Mederrick, who work between the two locations.

“When someone walks in, even though our shops aren’t huge, we have a great selection,” he says. “When someone asks if we carry a particular cigar, we usually have it. If not, we’ll find one to match their need. We try to carry more boutique stuff and things unique to our shop, so if we know what they like to smoke, we can give them something just as good or better.”

Señor Cigars has their own house blend cigar, the same one they’ve had for the past five years. Folks love them and they ship these cigars everywhere. “Where do you think they come back to every time they’re in Ocean City? They come to our shop, looking for that cigar,” says Mederrick. “You may only see them once a year and they come in looking for that cigar.”

“We pride ourselves in staying on top of what’s new in the industry,” he says. “You can’t carry every cigar because there’s thousands out there and you only have so much space. Unlike some shops, we spent time educating and listening to customers to make sure what we offer is something they’re really going to enjoy.”

“The only thing we don’t carry that you might consider high-end would be Davidoff, because you have to guarantee so much volume and it doesn’t fit our business model. Other than that, we pretty much carry everything.”

At Señor Cigars, they’re all about the customer. “At the end of the day, it’s not necessarily about knowing everything about the cigars,” he says. “In terms of staff, we look more at their personality and how they’re going to treat the customer. It’s about giving good service, making sure everybody who comes in leaves feeling like they want to come back—that’s what we do.”

He continues: “First off, you sell yourself. You’ve got to establish a rapport with customers and put them at ease. We always have music playing in the background, generally good blues. Customers walk in and you see their mood shift. We make sure the temperature’s right and the lighting’s right—those little things make a big difference.

“Once you greet them, you let them look around for a minute and then ask what they like to smoke. Immediately, that evokes a response. When you ask where they’re from, what brings them here, where they’re staying—you find you usually have something in common with the person. They really appreciate that you took time to talk with them, not just about cigars.”

When Señor Cigars introduces a new product, with or without vendor participation, they host a “Cut and Light,” inviting customers from their loyalty program. “We have about 600 members who get points based on their purchasing,” says Mederrick. “The first dozen or so people to respond get a seat at the table, and we get them to come in and give honest feedback.”

“As for a personal favorite, you never hang your hat on one cigar,” he says. “If I had to just pick a company, I would have to say Padrón. They control every aspect of their business, from box to label making. They’re never going to release a cigar early or speed up the process, ensuring the quality and consistency of their product. It’s an art form, really, a craft.

“There was a problem getting cigars for a while, because of the big surge from COVID. Companies that don’t make their own boxes, for example, couldn’t get packaging because the manufacturing facilities were shut down. Everything affects everything in terms of supply chain. You can see what’s happening today with all the ships sitting out there.

“We’ve been getting cigars and stockpiling a little to make sure we have products for next season,” he says. “We love trade shows but the timing doesn’t work well for us. We need cigars prior to our season and that’s when you want to get your specials. I’m still getting cigars we ordered earlier this year and don’t need them now.”

One of the biggest lessons learned from years in business is the need to control inventory. You can’t go to the shows and jump on every deal just because it’s “buy five get one free.” For shops like Señor Cigars, you really want to plan inventory to sell down this time of year to have as little as possible going into January, and then you start building back up. 

“Sometimes it doesn’t work to buy a lot of one brand just to get the free goods and have items just sit there,” says Mederrick. “You need the variety to be more lean and mean, and definitely take care of your ‘bread and butter’ folks in the off season—they’re the ones that help pay the rent and keep the lights on.”