There are plenty of places to grab a drink in downtown Annapolis, but Dry 85 has always felt like more than just another bar to me. I’ve been coming here regularly for more than eight years, and it remains my favorite spot downtown.
It works for almost any kind of night. I’ve stopped in for a quick bite and one drink, only to be home an hour later. I’ve also settled into a seat and stayed until closing. Over the years, I’ve rolled in solo, with a buddy, a group of friends, and family from out of town. It’s been my go-to spot whenever someone asks the question, “Where can I go eat in Annapolis?”
Tucked along Main Street, Dry 85 describes itself as a modern, industrial interpretation of a Prohibition-era speakeasy. Its name refers to the 85 days Washington, D.C., remained dry after Prohibition ended elsewhere in the country. The dark and cozy space opened in 2014 and was built around whiskey, craft beer, and made-from-scratch comfort food.
Starting With the Maryland Bourbon Trail
On this visit, we began with the Maryland Bourbon Trail flight, featuring Basil Hayden, Willett Family Pot Still and Old Grand-Dad.
The flight comes with a fun bit of local history. As anti-alcohol sentiment grew during the 1700s, Maryland distiller Basil Hayden Sr. reportedly led a group of Catholic families, including members of the Willett family, from Prince George’s and St. Mary’s counties to Kentucky. More importantly, it gave us three bourbons to compare side by side.
Dry 85 has long been known for its extensive whiskey selection, particularly bourbon, rye, and American whiskey. The beverage menu also includes whiskey flights, craft beer, and seasonal cocktails.
Cocktails That Are Never Boring
One of the best things about Dry 85 is its rotating cocktail menu. There is almost always something unexpected to try, whether the bartenders are experimenting with infused spirits, house-made syrups, fresh fruit, or ingredients you would never think to put in a drink.
This time, we tried the Cereal Killer Old Fashioned, made with Lucky Charms-infused Old Overholt rye, house-made marshmallow syrup and a blend of Jeppson’s Malört and Luxardo maraschino bitters. Yes, Lucky Charms. In an Old Fashioned.
It was playful with the rye and bitters keeping the marshmallow sweetness under control. It’s a cocktail that had me immediately wanting everyone at the table to try it.
We also ordered the Fuego Fresca, made with tequila, Banhez mezcal, freshly squeezed watermelon and lime juices, agave and a dash of saline. It was bright, smoky, refreshing, and the perfect summer cocktail on a warm Annapolis evening. Was I immersed in a conversation and didn’t even realize how quickly I slurped this down? Maybe…we don’t judge here.
Comfort Food Done Right
Drinks may get much of the attention here, but the food deserves its own spotlight.
The fried chicken sandwich featured chicken soaked in the restaurant’s secret marinade and served with thinly sliced pickles, lettuce, tomato and chipotle mayo on a buttered bun. Hand-cut potato chips came on the side.
The chicken was crispy, generously sized, and packed with flavor. And their housemade chips were exactly what you want alongside a sandwich like this. We may have asked for extras.
We also tried the warm skirt steak and quinoa salad, which brought together house-made fried goat cheese croutons, macerated grape tomatoes, and organic mixed greens. It comes with roasted shallot vinaigrette, but I got it with ranch dressing because I’m not classy. I need those fried goat cheese croutons as part of my final meal.
That mix captures what Dry 85 does well. The menu leans into familiar comfort food, but the kitchen adds enough unexpected ingredients and house-made touches to keep it interesting. The restaurant describes its approach as gourmet, made-from-scratch cooking, with in-house sauces and dressings. You have to get their sriracha ketchup if you get fries or chips. Trust me.
More Than a Favorite Bar
The bourbon, cocktails, and food are all reasons to visit Dry 85. But they are not the only reasons I keep returning.
After more than eight years, the bar is tied to a long collection of memories. Some nights have been quick and casual. Others have stretched on for hours. There have been celebrations, impromptu meetups, ridiculous jokes, and conversations that changed the way I thought about something.
That is what makes a favorite local spot special. Eventually, it becomes less about what is on the menu and more about the people you shared it with.
Still, an excellent bourbon flight and fried chicken sandwich certainly don’t hurt.
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