Ex-president Gerald Ford bought cigars and pipe tobacco from him. The racing legend Richard Petty dropped in while in town for the race.
He has conversed with the actress Elizabeth Taylor in front of his store and Sen. Fred Thompson, when in the vicinity of SideTrack Tobacco, stops by to bag some stogies.
Owner and entrepreneur of the SideTrack Tobacco shop in Bristol, Va., John Leonard has been in business for himself since 1981. That was since he was forced from a job where he worked his way up from the ground level to associate engineer.
Leonard then decided to pursue his dream of working for himself, which brought him and his family to the Train Station in the early ’80s.
Anyone who has lived in the area since the early ’80s remembers Bristol’s beautiful Train Station located next to the famous Bristol sign which welcomes visitors to her humble abode.
Leonard and his family started by selling flower arrangements; eventually a local businessman asked him to take over a popcorn machine, hotdog-vending booth and other snack machines.
The businessman needed more time to concentrate on his other moneymaking ventures so he and Leonard struck a deal. Leonard told him he would watch his machines. A few months later in December 1981, the machines were his and SideTrack Tobacco opened.
As a side note he still has the old popcorn machine, which said would always remain in his possession.
Leonard started smoking cigars at the age of 6 when his grandfather would throw down his half-smoked King Edwards cigars while playing cards.
Leonard, trying hard to emulate his grandfather, never realized at the time that his enjoyment of fine tobacco would become his life’s work.
Leonard traveled to Roanoke, Va., to learn how to buy and sell his cigars. The first year of business he bought $58,000 worth of cigars from his supplier in Roanoke.
The loan of $2,000 dollars to start SideTrack, borrowed from the owner of the Train Station, was already paid in full the first year.
His tobacco supplier in Roanoke turned out to be a hustler who was charging him the customer rate for the tobacco he was buying, so Leonard started buying cigars elsewhere after he found this out to be true.
Before the cigar boom of the mid-’90s, which Leonard attributed to radio talk show host Rush Limbaugh’s mention of his serious cigar smoking and the rise of Marvin Shanken’s Cigar Aficionado magazine, stogies only cost about $0.69- $1.
The Train Station closed in the mid ’90s and SideTrack Tobacco Shop moved down the street across from the Paramount Theatre.
Since the move into a more visible area, business has grown making SideTrack a mainstay in the downtown scene.
There’s a small sign inside of the shop reading: “Cows may come and cows may go, but the bull in this place goes on forever.”
It is not uncommon to stroll into SideTrack and happen upon a debate about politics, religion or sports, you name it.
As Leonard says, “take everything you hear in SideTrack with a grain of salt.”
SideTrack is the closest thing you will find to the television show Cheers, where everybody literally knows your name and you are glad you came. The regular customers are treated as family. This kind of atmosphere is possible since SideTrack is family owned and operated.
Leonard hopes to one day hand over the business to his daughter, Cindy, and her husband, Scott.
When asked about his clientele, Leonard said cigar and pipe smokers “are usually educated and around 28 years or older. They know how to enjoy a good cigar and if they don’t I teach them.”
Cigars at this time are more popular than pipes but in the wintertime pipe tobacco sales are up. He attributes this to the warm feel of the pipe in the smoker’s hand.
Cigar smoking is not just a fine piece of tobacco leaf to smoke but a way of life. It represents those persons who know how to enjoy quality.
Winston Churchill was not just Prime Minister of Great Britain during WWII but a lover of the cigar. Churchill was just named Cigar Aficionado’s Man of the Century, for those of you who smoke cigars know that the “churchill” size of cigar was named after him.
Leonard believes that the famous cigar aficionados like Winston Churchill and John F. Kennedy are not dead. He sees a rise in cigar smoking among college students and believes the tradition will carry on to the next generations.

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