Great dive bars usually benefit from proximity to an interstate, something about the lightly industrial vibes that come with the real estate that usually borders highway zones. Cincinnati’s Edwards Road, just a few feet away from Ohio’s man north-south interstate, I-71, features not one but two great dive bars in the argument for best in the city. Out of the pair, Pilot Inn is the seemingly elder stateman with a public record of a bar on site since 1937, the origins of Edge Inn Tavern just a block or so away a little more mysterious.

Without being clued in to the 1937 opening date for Pilot Inn, guessing that the Cincinnati dive bar stretched back into history that far would not be difficult. The understated awning out front, the bare bones block it sits on, the early opening hours to accommodate a lunch crowd, all of the variables add up to a classic bar built decades ago to serve anyone getting off of any shift hungry for some food or thirsty for a drink. Over time, Pilot Inn’s Hyde Park neighborhood has developed into a fairly desirable part of Cincinnati with more expensive drinking options prevalent just a few blocks away, but Pilot Inn endures as the counterpoint to that slow march of gentrification.

As the fortunes of the Wicker Park and Ukrainian Village neighborhoods have lifted over the years, Phyllis’ Musical Inn has remained unchanged, the structure’s same opaque glass blocks looking out onto Division Street. Clem Sr. passed in 1997, leaving Phyllis to preside over the space until her death at teh age of 93. Son Clem Jr. now manages and owns Phyllis’ Musical Inn alongside wife Ilene, thankfully preserving the many details that make the space unique, down to the striking keyboard & shot glass wallpaper picked out by Phyllis in 1955 affixed to the walls still today.

Maybe most surprisingly is the presence of a beer garden discovered through a small door in the rear of Phyllis’ Musical Inn. The striking setting feels more private than seems possible for such a densely populated corner of Chicago thanks to tall walls that block out all manner of exterior noise. A basketball hoop can be found here, evening drinkers often taking a small break from the live music inside to shoot a basket or two before reentry.