Downtown Annapolis is easy to explore by foot or hop on and off the free city electric shuttle. Small enough to cover in a day with enough sites, shops, restaurants and bars to keep you busy.
By downtown Annapolis I’m referring to the central area from the harbor up main street to St. Marks Church. From early in the morning with delivery trucks darting about through the bars closing at night, the area is alive with the sights and sounds of a popular harbor town.
Let’s start at the harbor as it is the heart of what makes Annapolis special. Standing at the Harbor Master’s office (corner of Dock and Craig streets) with Ego Alley to your right and the city mooring field straight ahead there is no doubt that Annapolis is a city built around the water. Unless the bay is frozen over during a nasty winter cold spell, you will see boats sailing about. Annapolis is the Sailing Capital of the US and it only take a few minutes looking around to see that is true. Masts with sails flying, boats darting about, and large motor yachts showing off in Ego Alley. If you are drawn to water, boats and the people who love them, you’ll find yourself standing at the waterfront with a big smile on your face. Look around and see how many people are smiling along with you!
Now turn and look up the hill towards the church steeple. You can see the Maryland state capitol to your right and St. Ann’s church ahead. Main Street is a terrific shopping street. Restaurants abound from casual to fancy. Irish pubs serving delicious fish and chips to everyone claiming to have the best crab cakes or crab chowder in the area. Being hungry is just not an option. One thing you might notice among the stores lining the street is many sailing-oriented stores. Our favorite two include the Sperry Shoe store and Helly Hanson.
Put on some Sperry Top Siders and grab a Helly Hanson sailing jacket and you just might find yourself being invited on to join the Wednesday night sail boat races.
Let’s head up the hill. About half way is Chick and Ruth’s.
An Annapolis institution. Diner, Deli and B&B all rolled up into a loud, cramped place that everyone loves. A little farther on the other side is Annapolis Ice Cream. If you’re like me all the food and shopping has tired you out and it’s time for an ice cream break! At the top of Main Street on the left is the Maryland Inn (and a Starbucks). This historic hotel is known for its warm rooms with balconies overlooking the street and the fancy Treaty of Parris restaurant in the basement.
What’s your favorite store or restaurant is along Main Street?