+ By Christine Fillat + Photos by Briscoe Savoy

A recent Sunday night was a noteworthy delight at the Dark Horse. Pittsburgh-based band Jukehouse Bombers galloped into town to deliver its particular brand of 1970s-inspired rock and blues. Three guitars brought to mind the verdant harmonies of the Allman Brothers, the velocity of Lynyrd Skynyrd, and the virtuosity of Crosby, Stills, Nash & Young. This lovable bunch of rock and rollers cranked out astonishing tunes, one after the other, with such powerful delivery— tunes with the slow, steady beginning, gaining in momentum, and exploding in orgiastic rock and roll badassery. Folks boogied on their barstools. The brave ones shimmied right in front of the band. And the Jukehouse Bombers rode on.

“I found them on Instagram,” says co-owner Kristian “Pinky” Gaines. “I’ll just come across musicians on Instagram and send them a message and, you know, ask them to play in our little music room in the neck of Annapolis.”

Dark Horse Annapolis

What Pinky calls “our little music room” is a comfortable sports bar and music venue. Televisions, lining all of the walls, feature sports activities happening around the world. The ceiling has been soundproofed, and dartboards have been hung here and there. The bar encircles the center of the room. The kitchen serves formidable bar food, items such as a popular burger and fish and chips. 

Dark Horse is owned by Pinky and her husband, Ryan Gaines, his brother, Steve Gaines, and Steve’s wife, Jen Krohn. They are also owners of the Annapolis Smokehouse & Tavern, just down the street. The couples created a business plan, and to run both businesses, they divide and conquer: Steve and Jen run the Smokehouse, while Ryan and Pinky run Dark Horse. Ryan has the day shift and Pinky takes the nights. Clearly, they spend most of their time there.

Dark Horse is the newest incarnation of the old Ebb Tide, an Annapolis neck standby for many years, located on Bay Ridge Road. “We got the keys on January 1 of 2020,” says Pinky. “We started renovations, and I was hitting ‘send’ for our soft opening on March 16. We were going to open on March 17, but the world shut down [due to the COVID-19 pandemic] on March 15. So it was kind of a bear. So we plowed through and opened that August, 2020.” 

Camille Bucci delivers a pint to Alex Ewing on a busy night.

When Dark Horse was ready for live entertainment the following summer, so were all the other music venues. “It was really hard to book local talent,” says Pinky. She had to look for musicians from outside of Annapolis. 

Since then, the venue has had many bands, local and from the surrounding area, to choose from, including acts such as Pretty Big Deal, Lee Priddy, Starbelly, Dennis Schocket, Moosejaw, Troll Tribe, and Candy Man & The Baltimore Show. Many genres of music are played, from bluegrass, rock, blues, and more. “I’m really excited by the next generation to come up, here,” says Pinky. “We have Honey Sol. We have the Severn River Band, they’re doing original music. If you have original music, please play it! Cal Toner. Her voice is incredible. She walks around the bar, singing her music.” Now, musicians are reaching out to Pinky for gigs at Dark Horse. Thursdays and Saturdays are booked through July 2023. 

Music is just one facet of Dark Horse, as it is also a serious sports bar. “We show every sport you can imagine,” says Pinky. Ryan and Steve, who are soccer fans, open the bar early on Saturday and Sunday mornings to televise the Premier League. The room sells out and gets pretty raucous. 

Troy Chittum and Collin Gardner doing their thing behind the bar.

Not every screen will always televise sports, though. One monitor in the corner has been known to show Bob Ross painting his iconic landscapes. 

The staff wear shirts with the image of a skinny nag, swaybacked and out to pasture. “[Dark horse] is an old horse racing term,” says Pinky. “It’s the horse, the underdog, the one that no one bets on but comes in from behind and wins the race.” This is an appropriate moniker for a new venue that had to weather the pandemic before it was able to come into its full potential.

Future plans for Dark Horse include a monthly sip and paint night in the game room, bluegrass Sundays, a paintball turkey shoot for charity, and more use of the parking lot for music and outdoor events. 

“We say that we’re everybody’s first stop and last stop,” says Pinky. “One of the most important things to us is the relationships that we have forged with our regulars. Now [they] are our dear friends that we call our families . . . that fill up our room every day. We love them and we’re grateful. I attribute much of our success to the people that come in.” █

For more information, visit DarkHorseAnnapolis on Facebook.