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Cheshire keeps its chic speakeasy vibes alive in new space

Owner Evvy Fanning gets a little help from her friends – not to mention staff – reopening her tribute to pre-Prohibition-era classic cocktails
Owner Evvy Fanning poses at the bar  of Cheshire Bar and Lounge in Rochester NY
Cheshire owner Evvy Fanning

There’s no sign out front at 695 South Clinton Avenue, only windows covered in dark lace curtains. But stepping in through the side door, you know you’re in the right place: the Cheshire Lounge, a stylish but welcoming bar with an abundance of atmosphere and charm.

“I think we got the reputation of a speakeasy because I don’t know how to market,” says owner Evvy Fanning. Her focus is on quality cocktails and a friendly atmosphere where all are welcome, rather than maximizing speed or profits. The bar specializes in vintage cocktails such as the Stinger, the Negroni, and Fanning’s favorite, the Old Fashioned. (She has, however, been known to invent new ones – check out the recipe for her (585) Cocktail below.)

“Classic cocktails are pretty simple,” she says. “It’s essentially seasoned booze.” Without mixers or extra ingredients to hide behind, it’s “bourbon that’s seasoned to bring out all the nuance of the bourbon. That’s a great Old Fashioned.” She explains that Cheshire prefers to revive pre-Prohibition-era classic cocktails rather than invent new ones. Almost everything on the menu is a resurrected drink.

It’s a lot of work to come up with exactly the right recipes for cocktails as they were intended to be a hundred years ago. “The ingredients we have now are just not the same, so we have to adjust the ratios,” she explains. But getting that balance right is a fun job. “Everything on the menu has been made a dozen different ways with different properties and different whiskies and different bitters.” It takes a lot of time, but by the time a cocktail goes on the menu, it’s exactly the way Cheshire wants it to be. 

A bartender mixes a drink at Cheshire Bar and Lounge in Rochester NY

The lounge, which opened on May 31 of this year, is the second incarnation of Cheshire, the bar having recently moved from its old location on South Avenue. The new space was renovated and decorated by Fanning and her staff of bartenders, and it was a labor of love. The people who work at the bar have become like family over the years, and for the past year and a half, she says, the renovation took place on evenings and weekends, “because they all have careers and day jobs like I do.”

It was a huge undertaking. The space had been many things in its past lives: It was a hookah lounge at one point and a Chinese restaurant at another. Covering the now-exposed brick was not only drywall but also “concrete and tile and wallpaper and mirror glued to the concrete.” Fanning and the staff completed the renovations and decorating with help from volunteers and community members. “You can point to anything in here, and there’s a funny story.”

A community of people has grown around Cheshire, she says, and people have been incredibly supportive and loyal, pitching in with design and even cleaning, painting, and wiring. “This place belongs to so many people,” remarks Fanning. She says that most of the furnishings are secondhand or things she or her friends already had. Pointing to a print on the wall, she says, “that picture used to hang over my bed when I was a kid in Latvia.”

In Latvia, Fanning’s grandparents held elegant cocktail parties, and that is where her love of the art of mixing drinks began. “Not going to lie,” she says, “I’ve ordered a cocktail based on what type of glass I’d like to hold.” She explains that the experience of drinking a cocktail needs to involve all the senses. The way it looks and the way it tastes are important, of course. But her grandfather taught her that the reason we clink glasses in a toast is to add an element of sound.

A cocktail with pink flamingo stirrer sits on the bar at Cheshire Bar and Lounge in Rochester NY

As an adult, Fanning spent a little over a year traveling to different bars that she’d read about—in New Orleans, San Francisco, London, and Paris, sampling drinks and asking questions, watching and taking notes. “Nobody ever taught me how to do it,” she says.

She now likes to hire people who haven’t gone to bartending school. Bartending school culture isn’t real or genuine, she feels, and she would rather train people. Aspiring mixologists should “pay attention” and go to a lot of places, she says, to see what they like, and work backward to try to figure out why they like it.

As far as advice for customers? Tip your bartenders. “Good servers who love their job and do it well make good money,” she says, and we all want them to stay in the service industry. Consider leaving a ten instead of a five, because “where else can you buy hero status for an extra five bucks?”

Fanning is a high school teacher during the day and says that the two jobs go surprisingly well together. By the end of the school day, she says, she is ready to be in an adult environment and have the one-on-one conversations that happen at Cheshire. And after an evening at Cheshire, which can get pretty busy, she is ready to be in charge of a classroom again. It’s a good, invigorating contrast. 

Fanning doesn’t believe in the concept of “work/life balance” per se. “There is not a clear separation between work and life. This is very much my life.” 

The (585) Cocktail, by Evvy Fanning

• 2 oz. of rye 

• 1/2 oz. of Riga Black Balsam (an amaro from Fanning’s hometown of Riga, Latvia) 

• 1/2 oz. of honey syrup (mix equal parts honey and water to make a syrup) made from local wildflower honey from Birds and Bees • finish with a dash of grapefruit bitters

Fanning notes: We like it shaken and served up with an orange twist. It’s smooth and shows some sweet and floral notes from the honey, but also a peppery kick from the rye. It has the familiar classic character of a Manhattan and some new touches from Rochester and from Cheshire. Tastes like home.

Cheshire 
695 S. Clinton Ave., Rochester, NY 14620
(585) 350-8128 

cheshirerochester.com

This article originally appeared in the November/December 2024 issue of (585).

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