The third oldest city in the United States, Portsmouth has a rich and colorful history that dates back beyond the American Revolution. But it’s just in the past couple of years that it has emerged as one of the hottest weekend and vacation spots in New England, fueled by an explosive culinary scene and its increasingly rare indie vibe, full of mom-and-pop shops and boutiques, without a single national chain retailer.
As one of the nation’s longest running tobacconists, Federal Cigar and its downstairs cigar bar fits the city perfectly, with a history in Portsmouth going back over a century. Originally United Tobacco, launched in 1904, it was renamed Federal in 1921 and continued in various locations before settling into a 200-year-old brick building on one of Portsmouth’s most prime corners, Market Square, the downtown epicenter.
The large retail store features over 1,800 different labels, including several exclusively made for Federal from My Father, Fuente and Quesada. The store has a history of celebrating its anniversaries and milestones with such releases, and the latest was the Quesada Federal 96, which commemorated the shop’s 96th birthday.
The kind of shop that would fit in on Manhattan’s Fifth Avenue, Federal is chock full of display cases and floor-to-ceiling glass cabinets, with an extensive selection of pipes, tobaccos, and a full range of accessories, including lighters, cutters and humidors. This is the flagship, but Federal also operates two other shops in southern New Hampshire (Dover and Epping).
Three years ago, the company expanded again by opening a deluxe cigar bar in the basement under the store, with an interior staircase when the shop is open, and a main outside entrance when it is not. Purpose built, it has a powerful state-of-the-art ventilation system. The bar is a real beauty, with a unique “classy contemporary cave” feel, thanks to the underground setting and dark, rough stone walls from the early-1800s foundation.
Everything else is highly polished, with rich curved leather banquettes, deep leather couches, and a long bar fronted by leather stools and topped with the variegated namesake stone of the Granite State. The main space is one long room with the bar down the left, the banquettes along the right, and the humidor—custom built into an original arch-shaped vaulted brick alcove—at the far end.
Beyond this is a second section, more living room in style, with freestanding easy chairs, couches and oriental rugs. By day this is the private members’ room, with a wall of lockers, but after 9 p.m. it’s open to everyone to accommodate nightly demand.
Between the luxurious furnishings, the bar menu with its focus on classic and pre-Prohibition cocktails, and the subterranean setting, there’s a not too subtle speakeasy glamor and allure to Federal Cigar. This is accentuated by the traditional martini glasses, cut crystal highballs, oversized cube ice program, and very impressive list of 120 whiskies, including several single barrel private labels exclusive to Federal, including Knob Creek, Woodford Reserve and Jack Daniels, There is a deep single-malt Scotch list, solid selection of high-end Japanese whiskies including Hibiki and Yamazaki, a fairly long wine list, and rotating selection of craft beers on draught.
There are about two dozen cigar options on the printed humidor menu downstairs, though when the store is open, guests can purchase and enjoy any smoke from the large humidor. By law, no food is served, but that’s about the only omission at this well stocked, well furnished, clubby spot that makes the most of its escapist setting.
It’s within a five-minute stroll of several of the most acclaimed Portsmouth restaurants, and as such is wildly popular after dinner. Portsmouth is a town known for evening revelry, and Federal Cigar is the only place in the entire city where you can smoke inside, and for the three years since it opened, both locals and visitors have been keen to do just that.
36 Market Street
Portsmouth, NH 03801
Open Monday through Thursday: 4 p.m. to 11 p.m.
Open Friday: 3 p.m. to 12 a.m.
Open Saturday: 12 p.m. to 12 a.m.
Open Sunday: 12 p.m. to 11 p.m.