Known by locals as DTA or Naptown, downtown Annapolis is a great place to pass a weekend afternoon if you ever find yourself in central Maryland. It has brick-lined streets and waterfront views to enjoy, not to mention some of the best food. Here’s an unofficial guide detailing all the things you have to do if you’re ever in Annapolis. If you’re like me and live there, you’ve got to do each of these at least once.
Get ice cream at Storm Bros.
It’s a tradition that’s been in the area for over 30 years. They make the best ice cream on Dock Street, and the prices are great. After you get your ice cream, you can sit on a bench and look out at the water or people watch (two things Annapolis is good for).
Get fried mac 'n' cheese bites from Pip’s Dock Street Dogs.
Their hot dogs are killer, but their fried mac 'n' cheese bites are indescribable. Served in a brown paper bag, you can get these on the go. The best part? They cost less than s.
If you’re a coffee fan, head to city dock.
Even if you aren’t, they have great teas and smoothies. A personal favorite of mine is iced chai tea with coconut. They also have great pastries and incredible Smith Island Cake, another Maryland favorite.
Tour the Naval Academy.
If you’ve never stepped foot on the campus, you’re missing out. There is so much history (and natural beauty) to see. The Severn River surrounds the campus and provides some pretty great views. You’ll probably see midshipmen walking around and get a feel for the tradition and history that Annapolis is built on.
Order the 6-pound milkshake from Chick and Ruth’s Delly.
Or just go to Chick and Ruth’s for brunch. But the milkshake is a must. Order it and split it between a few friends (or if you’re brave, try it yourself).
Go to Pusser’s.
The food is great, and you can’t beat the waterfront views.
Take a walk.
There is so much to see in Annapolis, and the streets and buildings are one of the most interesting parts. Make sure to walk up Main Street and down Maryland Avenue. If you like shopping, Annapolis is full of boutiques and unique stores to explore.
If you’re a reader, visit the Annapolis Bookstore.
They have everything from the classics to old maritime collectibles. Even if you don’t buy anything (I always do), it’s a cool place to walk around and look. Follow a spiral staircase downstairs, and there is a basement of books like you wouldn’t believe. They also have a great coffee shop and a garden out back.
Watch the boats going in and out of Ego Alley.
You’ll see some interesting and incredible things for sure. My favorite is watching massive boats chug down the alley and struggle to turn around in the narrow space.
Watch an Annapolis sunset.
To finish out the day, make sure you get a seat with a good view (get your ice cream if you haven’t already) and watch the sun set over the water.