Gypsy’s Mainstrasse

Covington, Kentucky

Field Note

Cincinnati and its surrounding area is full of hidden gems, many of them the result of a long history of German heritage in the region. Over-The-Rhine may get the attention, but just across the river in Convington, Kentucky, sits Mainstrasse Village, a classic, German-inspired walking district packed with history-rich buildings, bars and restaurants. Gypsy’s Covington cuts a sliver of a silhouette into the district, a shotgun style dive bar in a brick-lined building easily mistaken for a residence.

Opened in 2015, Gypsy’s is part of a network of bars and restaurants that span Cincinnati and its northern Kentucky orbit owned by Juan Imeroni and his Imeroni Entertainment company. The Imeroni portfolio includes fellow Cincinnati dive bar O’Malley’s in the Alley as well as a handful of less divey options. Gypsy’s occupies a bit of a middle ground, pairing an authentic space and well-worn building with a bit of polish that elevates he bar past true ‘dive’ status.

The Gypsy’s exterior can be easy to miss despite a pair of black signs hanging over the door thanks to the way the building fits seamlessly into its neighborhood. Mainstrasse Village feels a bit like a small town Main Street merged with the narrow plots and weathered buildings native of a European town. Gypsy’s plays into that vibe with exposed interior walls supported by dark wooden beams, allowing the beauty of this original space to shine through.

Vibe aside, there are more than 80 beer options to explore here and the back patio is perhaps the best place to explore them. Hidden gem within a hidden gem, the Gypsy’s patio is one of the best patios in the Cincinnati area, mixing cozy confines with a bit of seclusion thanks to high walls and a pergola over head. During summer months, the patio’s shade can be a relief and when the weather turns, Gypsy’s closes ranks a bit to insulate this outdoor space.

Because of its low key, neighborhood location, the patrons assembled here are often regulars, often living in close proximity. Gypsy’s has long been a champion of the Covington Street Hockey League as just one example of the Cincinnati dive bar’s integration with its community. That tight knit neighborhood relationship paid off in 2023 with the delivery of a game ball from the Cincinnati Bengals after a playoff win over the Buffalo Bills that year. The program recognizes the shared success of team and community after playoff wins by giving thanks to the hubs of fandom and support around the city, including Gypsy’s.

Wednesday night is karaoke night at Gypsy’s and a live DJ typically takes over Friday nights. The space is both dog friendly and hockey friendly, a rarity among other Covington drinking options. NHL games and major hockey events are regularly broadcast on the set of TVs found dotted throughout the dive bar. The area behind the bar adds a bit of class to the space thanks to backlit and illuminated liquor bottles along shelves set against a backdrop of bricks. Dollar bills, many of them inscribed with the name of a favorite hockey team add a live dive bar balance.

The floorplan itself is straightforward with a long bar on one side of the building and a bit of seating along the opposite wall. Rows of string lights, framed photos of regulars and a fair amount of beer-friendly signage round out what Gypsy’s classic dive bar ambiance. A small stage toward the front of the building serves as anchor to karaoke, DJ and other special event nights.