Where Everybody Knows Your Name
Cypress Cigars
Where Everybody Knows Your Name
Story and Photos by Sophia Hyde
Lynette Rogers:
About five years ago Tom and I were in Daytona. He took me to a cigar shop on State Road 40. I immediately fell in love with the atmosphere, even though I had never been a cigar or cigarette smoker. Before you knew we had been there for four hours and I went threw a few cigars and a couple drinks. I met people some of the nicest people I would have never met and heard their stories. Although every cigar shop is different, they all share one similarity. Once you put a cigar in people's hands, everyone is equal and they just want to relax together.
Tom Ziegler:
Growing up my parents always smoked cigarettes but I never liked the smell.. Like all kids, I did sneak one a few times from my parents pack of Viceroys.My Mom's dad who we called . Grampa was an engineer for the Frisco Railroad in St. Louis.He'd come an visit while we were in school. We would come home after school and, the house would smell like cigars.That's how we knew Grandpa had been there and he would leave us 4 dollas cash.one dollar for each kid..I always loved the smell of his cigars.
One day I went with Granpa to the cigar shop where he would buy his boxes of cigars. I loved the place. It was old, smelled like cigars and I KNEW this was kind of place.. When we left that day, Grandpa gave me my first cigar and said "don't tell your Mom, she'll kill me." I've loved cigars ever scince In my cigar shop hangs a picture of Gramdpa Sweatt .
Memories and cigars just seem to go together especially for me THANKS GRAMDPA!
Sam Killebrew:
I quit smoking cigarettes 30 years ago. On my 50th birthday, an employee gave me a box of cigars. I became a casual smoker after than and would occasionally come in and buy one or two cigars from Ray. I love this environment and wanted to keep something like this here in Winter Haven, so mainly I become an owner here for selfish reasons. I wanted to be able to keep coming.
Can you hear the music? Because the moment I walked into this place I immediately started hearing the lyrics in my head “where everybody knows your name…and they’re always glad you came.”
Cypress Cigars really is Winter Haven’s version of Cheers. Yes they sell cigars, but that’s not why people are passionate about this hole in the wall hang out. It’s the relationships. Just like Cheers wasn’t really about the beer, the draw for most people to step through the doors of Cypress Cigars is to leave their worries outside and relax in an environment where everyone cares about each other.
You can’t truly appreciate the uniqueness of this shop if you don’t understand the background story. Ray Barkley is the heart and soul of Cypress Cigars. After being a cigar aficionado for 30 years, when Ray retired he opened his own cigar shop in downtown Winter Haven, The Board Room. He was very knowledgeable about cigars, and passionate about people. Many people in Winter Haven would come and smoke a cigar with Ray to forget about everything else in the world.
Lynette Rogers and Tom Ziegler were two of Ray’s regulars. Lynette would often say when entering The Board Room, “I would love to own a place like this!” They loved the atmosphere so much that they converted their formal living room into a cigar room in their own home. It became a common after work hangout for them, and they invited their friend Sam Killebrew to join them. Over the next few years it became a second home for many people in Winter Haven to relax.
At the end of 2009, Ray was going to close his doors. It was disappointing news to everyone who had come to love his place. Tom and Sam were having a drink at Ave Bar discussing the discouraging situation. On a whim someone threw out the idea of taking it over and talk started getting a little more serious. They decided to meet for breakfast the next morning at Richard’s Coffee. Twelve hours later Tom, Lynette and Sam met for breakfast and fell in love with the idea of joint owning the cigar shop and keeping Ray in business.
Meanwhile, Ray was piddling around the house, procrastinating going into work that day because he had decided it was the day he was going to hang up the closed sign. When he walked up to the store, the trio was already waiting on him, and thus was the birth of Cypress Cigars.
Over Christmas break the shop went through a three-week renovation and Tom completely transformed the interior. The unveiling of Cypress Cigars was on January 11, and since then the people just haven’t stopped coming. And most likely, Ray has learned every single one of those faces by name too.
What is most fascinating about Cypress Cigars is not anything extravagant, rather the opposite. People love it because of the intimate details. Every cigar is hand made, nothing machine produced. When you buy your cigar Ray personally cuts it, soaks it in Cognac and lights it perfectly. At 4:00 every afternoon the lanterns on the wall are lit. A figurine of the only Disney character with a cigar in his mouth, Lampwick from Pinocchio, rests in the front showcase. No cigar box is ever thrown away. If not given away, they are made into custom purses. The minute details go on and on.
Both men and women who had never thought of themselves to be cigar smokers, can’t help but fall in love with the atmosphere. The air is kept extremely clean, so you’re not walking into a smoky atmosphere, and you don’t leave smelling like a cigar.
Take Jenny Polhemus for example. Jenny is a long haul driver from Wisconsin who routinely comes through Winter Haven, but not without stopping by Cypress Cigars. “I come as often as I can,” she said. “The customer service is the best.”
Her opinion doesn’t differ much from Russ “Rusty C” Clifford who has been a regular since January. “Ray is the reason I come. The customer service is the best. He goes out of his way to do more than most people. It’s just a nice, friendly atmosphere,” he said. “It’s the best place to just come and relax.”
On the afternoon I was in the shop, the testimonies just kept coming. Everyone who came through the door wanted to express why they loved this place. “I come here because of Ray,” said Ivan Hicks.” He knows his cigars. Everybody knows everybody. The customers will pitch in and help Ray out if it gets too busy. I’m here everyday; I think I practically live here.”
The stories could keep on coming, but the reality is, you need to develop an opinion for yourself. If you live in Winter Haven, you should not deprive yourself of this little gem in downtown. Stop in and visit Ray, he’ll quickly know your name.


