The Best Ice Cream Shops in Annapolis

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Annapolis has its fair share of ice cream shops. But it’s tough to tell which is the best. Especially when four of them are within 1,500 feet of each other. Here’s a pro tip: you can’t go wrong with any of the Main Street shops, but there’s a clear winner.

Now the list…

5. Smallcakes

Smallcakes peanut butter ice cream chocolate chip sandwich

Smallcakes Cupcakery doesn’t just serve up delicious baked goods. They also craft several flavors of small-batch ice cream every day right in their Parole shop!

During my recent visit, I ordered an ice cream sandwich. I figured it was the perfect way to try their homemade ice cream and signature baking. The chocolate chip cookie was sturdy on the outside and soft on the inside—a perfect wrapper for my peanut butter cup ice cream. And yes, it tastes as rich as it sounds.

If someone in your group wants more choices than ice cream (or you just don’t want to fight downtown traffic), Smallcakes is the place to go.

2641 Riva Road, Suite F

4. Kilwins

Kilwins pistachio, All-American two berry pie, and blueberry waffle cone ice cream in a waffle cone cup

If you’ve ever strolled down Main Street, you’ve probably smelled Kilwins. It’s like walking by an Abercrombie store at the mall. Except instead of high school cologne, it smells like Willy Wonka’s chocolate factory.

And you’ve probably watched the team hand dip caramel apples and paddle their classic fudge. But have you tried their homemade ice cream?

Kilwins ice cream has been made from the same recipe since 1985. And while it’s not made in store, Kilwins manages the whole process from mixing to shipping so it’s always high quality.

128 Main Street

3. Storm Bros.

Storm Bros. key lime pie and raspberry truffle ice creams in a sugar cone

Ego Alley’s historic ice cream parlor, Storm Bros., is the perfect place to grab a cone before strolling the docks. And even if they aren’t number one for ice cream, they’re definitely number one for views.

Storm Bros. opened in 1979 and is still owned and operated by the Storm family! The extensive ice cream display, framed by a bright red brick wall (great for Instagram) will have your mouth watering as you choose your flavor. Summer classic key lime pie is my go-to. But nothing at Storm Bros. ever disappoints.

130 Dock Street

2. The Red Bean

Red Bean’s Old Bay pretzel ice cream in a waffle cone

The Red Bean has the most unique flavors on this list. And as an added bonus, they source ingredients from several local partners—most prominently Middletown’s South Mountain Creamery. The Bean was born out of a dream to offer the most delicious and distinct ice cream around, and it sure does deliver.

Ever had Old Bay pretzel ice cream? What about a cinnamon, chocolate and chili concoction? Or if you’re the creative culinary type, build your own masterpiece. Red Bean has over 50 mix-ins for your confectionery pleasure.

Full disclosure: editor Ryan might prefer “hard ice cream”, but I’m a sucker for soft serve. And this charming Main Street joint never lets me down. I ordered the Old Bay pretzel with some trepidation, “Hmmm… this may taste awful” but BOY WAS I WRONG.

It was the best soft serve ice cream I’ve ever had.

220 Main Street

1. Annapolis/Always Ice Cream Company

Always Ice Cream Company raspberry chip and vanilla ice creams in a waffle cone

It’s no surprise AIC tops this list. After all, this sweet little shop has earned “Best Ice Cream in Annapolis” 18 years in a row. Lucky for us, they’re making big moves. To complement the original Main Street location, they now have a second store and truck under their new brand: Always Ice Cream Company. And there’s another store on the way.

Annapolis’s premier parlor serves up the classics, seasonal specials, vegan ice cream, and always has a local partnership running. Right now it’s Carlson’s Donuts and Double T Diner cookies. My two favorite flavors are lemon poppy seed and the electric blue cookie monster.

You can’t go wrong with the original location on Main Street. But for our West Annapolis friends, you can avoid the downtown craze at the first location of the new brand, Always Ice Cream. Either way you’ll indulge in Annapolis’s #1 ice cream!

Annapolis Ice Cream Company – 196 Main Street

Always Ice Cream Company – 116 Annapolis Street

Honorable mention – The Daily Scoop

The Daily Scoop brownie batter and coconut chip in a chocolate and rainbow sprinkle dipped waffle cone

No Maryland ice cream ranking is complete without at least mentioning Pasadena’s Daily Scoop. They’re just outside the Naptown Scoop’s radius (10 miles from the State House). So we couldn’t include them in our top five. But since it’s close enough, we had to acknowledge the 100+ delicious house-made flavors. If you ever find yourself in Pasadena, don’t miss this retro-styled gem.

3201 Mountain Road #109, Pasadena, MD 21122

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