Craig Smith

Craig Smith is the executive director of the Downtown Napa Association.

J.L. Sousa/Register

The first thing you notice when walking into Sidestreet Fine Cigars & Luxury Accessories in the Napa Riverfront Building, is the absence of a distinct cigar aroma.

It’s there, but faint, and blended with the smell of wood and leather, creating instead a calming atmosphere. Owner Shawn Dougherty, while immaculately dressed and a man of obvious style, is down to earth and unassuming.

Dougherty created Sidestreet as two businesses– a retail shop, featuring cigars and gift items, and an exclusive, private members only club. Both are extremely well thought out and executed.

Sidestreet is an homage to his grandfather, an airline pilot in the 1950s and ‘60s. “My grandfather believed in the Glory Days, when people would dress up to go out or entertain,” said Dougherty.

Growing up, Dougherty ate breakfast with this grandfather nearly every day, listening to stories from that era while Frank Sinatra, Tommy Dorsey and the Big Bands of the day played on the stereo.

An open letter to his grandfather is mounted at the entrance to the private club. It perfectly describes what Dougherty wants Sidestreet to be, and conveys the deep love he had for his grandfather.

On the retail side, Dougherty offers a carefully selected blend of boutique handmade cigars from Honduras, Nicaragua, and the Dominican Republic.

Sidestreet is also the exclusive provider of Davidoff Cigars in Napa Valley, and even carries a cigar wrapped in 24- carat gold for those ultra-special occasions.

Non-cigar items include Maui Jim sunglasses, as well as leather goods, hats, shaving kits, wine carriers and totes.

The membership club is unlike anything else in Napa. Private lockers, each a humidor and made from dark woods, identified with brass nameplates, line the walls as you enter.

A closet holds members’ smoking jackets. The Founders Room offers plush leather seats and a blazing fireplace. The Sinatra Room, dedicated to Dougherty’s grandfather, is adorned with pictures of the Rat Pack in their glory days.

Dougherty’s favorite room, the James Bond Room, features memorabilia from the Bond series, including signed photographs of all the Bond girls. Even the bathroom, which includes a powder room for the women, is perfectly appointed.

Trying to describe the interior somewhat misses the point though. Dougherty has created a space in which people can relax and be completely comfortable, while maintaining standards that Dougherty’s grandfather would have expected from people.

Dougherty has thought of everything to make these spaces almost home, and if he missed something that a member recommends, he adds it. Members are carefully screened.

“Sidestreet is a family,” said Dougherty. “It represents the heart and soul of values that members are passionate about.”

Sidestreet retail is open daily to the general public and located on the river side of the Riverfront Building, next door to the newly opened Basalt restaurant. Call 254-7900 or visit

See you downtown!

Craig Smith is the executive director of the Downtown Napa Association. Reach him at 257-0322 or


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