Cheshire

Cheshire is a speakeasy-style cocktail bar in Rochester's South Wedge neighborhood, operated by owner Evy Fanning. The bar originally opened on South Avenue, where it ran for over a decade before closing in August 2022. After an 18-month renovation, Cheshire reopened at 695 South Clinton Avenue on May 31, 2024. Fanning, who also works as a high school teacher, developed her interest in cocktail culture through her grandparents' gatherings in Latvia and later traveled to bars in New Orleans, San Francisco, London, and Paris to study mixology.

Cheshire focuses on pre-Prohibition-era classic cocktails, emphasizing historical recipes over modern inventions. The drink menu includes staples such as:

• Old Fashioned
• Negroni
• Sazerac
• Stinger
• Manhattan
• Whiskey Sour

The bar also serves a house original called the (585) Cocktail, made with rye, Riga Black Balsam, honey syrup, and grapefruit bitters. Private event hosting is available by request. Hours run Monday through Thursday from 5 to 11 PM, Friday from 5 PM to midnight, and Saturday from 6 PM to midnight. The bar is closed on Sundays.

Cheshire earned a spot on Esquire magazine's list of the top 10 cocktail bars in the world in 2019, a distinction tied to its commitment to carefully prepared classic drinks. The interior features secondhand furnishings and Latvian family memorabilia collected by Fanning, contributing to a dim, vintage atmosphere. True to its speakeasy concept, there is no sign out front — just windows covered in dark lace curtains, with the entrance located on the Gregory Street side of the building.

Cheshire sits at the corner of South Clinton Avenue and Gregory Street in the South Wedge, a walkable neighborhood south of downtown Rochester lined with independent shops and restaurants along its main corridors. The entrance is on Gregory Street rather than Clinton Avenue, so first-time visitors should look for the unmarked door on that side. The South Wedge is accessible from downtown via South Avenue or Clinton Avenue, and street parking is available in the surrounding residential blocks.