Annapolis, Maryland Best Things to Do

A weekend getaway to Annapolis — a small town filled with history, delicious food, and a scenic waterfront — sounds too good to be true. This is not the case. Annapolis is a short drive for us (about 3.5 hours), so we left after work on Friday and returned on Sunday without being exhausted. It’s an easy drive from Washington, DC, and Northern Virginia as well, so if you’re taking a mid-Atlantic trip, it should definitely be on your itinerary. Annapolis has its own charm and personality that is often overshadowed by bigger and busier Baltimore.

On a weekend getaway to Annapolis, I was happy to plan a walking tour of some of the city’s historic sites, with a focus on food and time to explore .

Au Sommaire

Morning in Annapolis

A weekend isn’t enough to explore ANY city, so we had to make a condensed version and cut out some things. Depending on your interests, you can add or subtract things as you see fit (one of the benefits of google maps!).

Breakfast is the most important meal of the day, so start the day off right and head to Sofi’s creperie. With a few locations in Maryland, the one in Annapolis is right by the waterfront. With an extensive menu of sweet and savory (and even gluten-free) pancakes, you’re sure to find something you like. There is a small seating area outside the creperie, or you can take the crepe to the water’s edge. My favorite thing about Sofi’s is their commitment to reducing their carbon footprint. They fold the crepe and wrap it in aluminum foil – so no polystyrene plates, plastic forks or knives – just delicious.

If you are a Christmas aficionado like me, before starting your visit, stop by the Christmas corner of Guzzi Gifts! They have lots of ornaments, including unique Maryland ornaments. The decorations of Christmas are one of the things that we collect on our travels. So, at the end of the year, we can enjoy all our trips again! As a bonus, you support a local business!

After breakfast and some Christmas shopping, it’s time to burn some calories with a walking tour of the city. At the end of the street you will see the entrance to the United States Naval Academy. If you like military history and culture, this is a must see place. Unfortunately, we decided to skip it so we could enjoy more of the city and its history. You can easily spend most of a day at the Academy – it’s also a source of pride for the city. Navy pride can be found in most shops and homes in the neighborhood. The entrance near Guzzi Gifts allows you to walk through part of the Academy, bypassing airport-like security.

Annapolis is very walkable and it’s easy to get carried away by the laid back atmosphere. Be careful when walking, the sidewalks are not always flat!

historic houses

There are plenty of historic homes to explore during your weekend getaway to Annapolis. On Prince George Street you will find the homes of two famous Marylanders: James Brice and William Paca. James Brice was an American planter, lawyer and politician. In 1792 he was Governor of Maryland and one of the largest landowners on the East Coast. His home is one of the most elegant historic homes in Annapolis.

A short walk from this house is the William Paca House & Garden. William Paca was one of four signers of the Maryland Declaration of Independence. Visits to the first floor, the whole house and the garden are chargeable (between 5 and 12 dollars depending on the visit). It is a five-part Georgian mansion built in the 1760s. Historic Annapolis and the State of Maryland restored it to its 18th century glory and it is still a National Historic Landmark.

Afternoon in Annapolis

Continue on Prince George Street, then turn right on Maryland Ave. Remember how I told you to keep your eyes peeled for cool shops? This street is home to one of the most beautiful bookstores! The Old Fox bookstore looks like a small shop, but as you walk in you’ll see it has a big personality. It smells of books and the atmosphere is such that you can snuggle up with a blanket and stay there all day. For lovers of deep L, there’s a cafe in the back that offers unique blends. Downstairs you’ll pass through Harry’s bedroom, where you’ll find more books and a few chess sets to play.

The little details are one of my favorite parts of the store: a picture of Gilderoy Lockhart in the bathroom (Harry Potter fans will understand) and a “blind date” book basket, where the books are packaged in such a way that you cannot judge them based on the cover but rather on a short description. But the best part is the back garden. A knight greets you before descending into the seating area which has a chandelier and a small pavilion for children.

The little details were one of my favorite parts of the store – a picture of Gilderoy Lockhart in the bathroom (Harry Potter nerds will understand) and a basket of blind date books – where the Books are packaged in such a way that you cannot judge them on the cover but rather on a short description. But the best part is the back garden. A knight greets you before descending into the seating area which has a chandelier as well as a small pavilion for children.

It took a lot of strength to leave this bookstore – but we did our shopping and continued on our way. The next stop was the Hammond-Harwood house which was built in 1774 as a five-part brick house. The main parts of the house are linked together by small tunnels or “hyphens” – a design characteristic of a 1570 architecture book and the only extant work of colonial academic architecture. House tours are typically offered daily for $10 (adults), $8 (seniors and students), and $5 (children).

Return to the Old Fox Bookstore and continue on Maryland Ave towards the State House of Maryland. The State House has an impressive history: it is the oldest US state capitol in continuous legislative use, dating from 1772. Tours are held daily. You can also see a statue of George Washington in the State House.

Continue around the State House toward Annapolis Circle, also known as St. Anne’s Circle because of the Episcopal Church located there. The circle connects most of the city and is surrounded by shops and restaurants. Rams Head Tavern and Reynolds Tavern & 1747 Pub are right next to the circle. Please note that the Reynolds Tavern sometimes offers afternoon tea – so you might find a group of very fashionable women drinking tea and eating small sandwiches (yes – it was a What a surprise to go there for a beer!) It’s up to you where you want to eat but there are plenty of places to satisfy the palette on Main Street. There is also a lot of shopping!

Every time I’m in a coastal town I have to go for fresh seafood and we absolutely LOVED Mason’s famous lobster rolls. It’s not for nothing that they are famous! Spencer had a lobster roll and I had lobster macaroni and cheese because…. Macaroni and cheese. I think what we really liked about Mason’s was its simplicity – no gimmicks, no fancy toppings, just lobster – oh, and butter.

For an afternoon break and a drink, stop by Red Red Wine Bar (which serves more than just wine!). Our server was fantastic – not only was he knowledgeable about wine, but he was also funny and friendly. Once you are ready to keep walking, continue on Main Street. The lobster roll filled me up a bit, but there’s ice cream and Uncle Bob’s Fudge Kitchen for those with a sweet tooth.

There is a small park between Main Street and Market Space where you can listen to live music. The Kunta Kinte Memorial is not far from this park. The original plaque that was placed in the 1980s was quickly removed by the KKK. Annapolis participated in the slave trade. Author Alex Haley was able to trace his roots back to Kunta Kinte’s arrival at the Port of Annapolis. His family’s story is told in his book and in the movie Roots. There is now a basis for teaching heritage and accepting differences.

We paused to freshen up at the Air BnB before going to dinner at the Federal House in downtown Annapolis. I couldn’t deprive myself of a crab appetizer, but there are plenty of delicious dishes, including vegetarian, vegan and gluten-free! The restaurant is also dog-friendly, with outdoor seating and a dog-friendly menu! Founded in 1830, the Federal House is also a place of history!

We ended our evening at the Harvest Bar across the street for a Saturday night karaoke!