What to do in Annapolis
Figure out what to do in Annapolis from waandering around the City Dock and Main Street to crabcakes and boat rides. My grandparents lived in Annapolis for around 19 years before moving to Boulder, CO. My family would spend most of our summers in Annapolis visiting them (and I spent one year of elementary school here). You’re getting a classic Annapolitan tour!
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Annapolis Walking Tour
Get straight to business and start the Annapolis walking tour I’ve given over the years to countless friends and family. Shout out to my grandparents for being the inspiration and the first people to give me the tour over the years. If you want something totally different, check out this ghost tour!
How to get to Annapolis
You’ll want to drive to Annapolis. There are no easy public transit options. If you’re planning a short jaunt around Annapolis, it is best to park right by the City Dock.
Park in the parking lot on Compromise Street. You’ll hit the lot first when you drive into town. If this looks full, you can drive up and park at Dock Street. Dock Street is street parking for around $2/hour.
What to do in Annapolis
Stare at the Boats
Walk along the Annapolis City Dock and stop along to check out the boats. You can take boat rides around the Chesapeake Bay from here.
Spa Creek Drawbridge
Walk up and down the drawbridge to see the yachts. The boats radio the drawbridge master to raise the bridge. My brother and I used to share this task on my grandfather’s sailboat when we would go out fishing! If you’re lucky, you’ll get to watch the bridge go up.
Stop in the Historic Annapolis Museum
This small museum will just take you about 10-20 minutes to walk through and read about the history of the town.
Main Street
Walk up Main Street towards Church Circle.
As you walk up the main street, take a peak onto Francis Street for this view. It’s less crowded!
On Main Street, look out for the best ice cream: Annapolis Ice Cream Company. I loved this as a kid because there are penguins in the window.
Most of the stores over the years have changed. There is a lot of turnover here and several fires over the years have caused damage to the historic buildings. One classic store is Irish Traditions. It’s literally Irish things but it’s fun to walk into. I used to buy all my gifts for my mom and grandma here.
Visit the Maryland State House
Once you get to Church Circle, turn right towards State Circle. This is the Maryland State House. You can walk into the State House and see some of the old rooms and read a bit about George Washington here.
From the State House, you can also see the Government House of Maryland and Lawyers Mall.
There is also a replica of the Liberty Bell.
Walk down Prince George’s Street
Walk to Old Fox Books and Coffeehouse and walk down Price George Street to see some historic houses. William Paca House & Garden is located here and you can tour the estate and garden. Other houses in this area include the Chase-Lloyd House—one of the signers of the Declaration of Independence—and the Hammond-Harwood House. Full disclosure: I’ve never been inside these houses. But they look cool!
Visit the Naval Academy
Some of the most vivid memories I have of a child are waking up to go fishing with my brother and grandfather. We would pass by the Naval Academy in the early mornings and peak at the students up early in the morning for physical training.
You need an ID to enter the premises if you’d like to wander the grounds and if you’re an international visitor, bring your passport as your ID.
Festivals in Annapolis
Annapolis has festivals and activities for the whole family. Plan for crowds and pricey parking to enjoy the festivities.
Independence Day Fireworks
The fireworks at City Dock in the summertime are a perfect way to spend the 4th of July. There is usually a parade and live music throughout the day.
Christmas Lights Boat Parade
The Annapolis Christmas Lights Boat Parade is a fun Annapolis tradition. A boat parade takes place on the second Saturday of every December. Boats are decked in lights and fanciful holiday decorations and parade through Spa Creek and the Severn River.
Where to Eat in Annapolis
There are tons of bars and restaurants around the City Dock on Main Street. My family has a couple of staple spots and we don’t experiment much more. If you find something amazing, please tell me about it for my next visit! For some history and food, check out this foodie tour.
Afternoon Tea at Reynold’s Tavern
Go for a classy tea time at Reynolds Tavern and 1747 Pub. My family had a gals brunch at the Tavern during the summer and it was so lovely. We picked the Afternoon Tea option for around $27 each. The service included a pot of tea each and then scones, finger sandwiches, and pastries to share. Check out the menu here.
Annapolis Classics
Market House looked like it had some good coffee and sandwich options. The Market House has never been able to hold down a tenant for a long time. I was attacked by a seagull right outside the Market House as a kid because it wanted my fry. It got the fry.
AnnAPusser’s Caribbean Grille is a great spot for quality fish and crab cakes. The vibe is a little old-school but it’s a classic! I’ve been countless times with my family over the years for lunch. There are also waterfront tables if you get lucky. If you’re set on going here, you may want to make a reservation.
Buddy’s Crab & Ribs is another Annapolis classic. The crab cakes here are amazing and the food is perfect for take-away so you can sit on the dock and enjoy. Just watch out for greedy seagulls.