Weekend Getaway to Annapolis, Maryland

Annapolis, Maryland is a quaint city with lots of personality! This city should not be missed even for a short weekend away.

A weekend getaway in Annapolis – a small city filled with history, delectable food, and a quaint waterfront sounds too good to be true. It’s not. Annapolis is a short drive for us (about 3.5 hours) so we left after work on Friday and came home Sunday without being exhausted. It is an easy drive from Washington, DC, and Northern Virginia as well, so if you’re doing 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.

With a weekend getaway to Annapolis, I was happy to plan a walking tour of some of the historical spots of the city, with an emphasis on food, and time to just explore.

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Morning in Annapolis

One weekend is not enough time to explore ANY city, so we had to do a condensed version and cut some things out. Depending on your interest, you may want to add or subtract things as you see fit (one of the benefits of google maps!).

My delicious crepe!

Breakfast is the most important meal of the day, so start the day on the right foot and head to Sofi’s Creperie. With a few locations throughout Maryland, the Annapolis location is right near the waterfront. With a full menu of sweet and savory (and even gluten-free) crepes – you’re guaranteed to find something you’ll enjoy. There is a small seating area outside the creperie, or you can take the crepe down to the waterfront. My favorite part about Sofi’s – their commitment to lessening their carbon footprint. They fold the crepe and put it in a foil wrap – so no styrofoam plates, plastic forks, or knives – just deliciousness.

If you’re a Christmas aficionado like me, before starting your tour, stop at Guzzi Gifts’ Christmas Corner! They have a LOT of ornaments, including some unique Maryland ones. One of the things we collect on our travels is Christmas ornaments, so at the end of the year we get to enjoy all of our trips again! Bonus: you’re also supporting a local business!

After breakfast and some Christmas shopping, it’s time to burn some calories with a walking tour of the city. Right down the road, you’ll see an entrance to the United States Naval Academy. If you’re into military history and culture, then this is an absolute MUST-see. Unfortunately, we decided to skip it so that we’d be able to take in more of the city and history. You can easily spend the better part 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 houses in the neighborhood. The entrance near Guzzi Gifts allows you to walk some of the Academy, without going through the airport-like security.

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

The quaint roads are easy to walk along during your weekend getaway to Annapolis.
Quaint roads of Annapolis

Head north to Randall Street and up to Prince George Street. Keep an eye out for some unique local shops – like Resails – which makes products from sails of ships! While they can be pricey, they are very durable and sturdy.

Fun Fact: Annapolis became the first peacetime capital of the United States when the Continental Congress ratified the Treaty of Paris on January 14, 1784. The Treaty established the USA as an independent nation.

Historical Homes

There are plenty of historical homes to explore during your weekend getaway to Annapolis. While on Prince George Street, you’ll find two famous Marylanders’ homes – James Brice and William Paca. James Brice was an American planter, lawyer, and politician. In 1792 he was the Governor of Maryland and one of the largest landowners on the east coast. His house is one of the most elegant of Annapolis’ historic homes.

Historic Maryland Inn
Hammond Harwood House

A short walk from that house is the William Paca House & Garden. William Paca was one of Maryland’s four signers of the Declaration of Independence. A small fee is charged for tours of the first floor, the whole house, and the garden (range in price from $5-12 depending on the tour). It’s a five-part Georgian mansion built in the 1760s. Historic Annapolis & the State of Maryland restored it to 18th-century glory and it is still a National Historic Landmark.

Afternoon in Annapolis

Continue down Prince George Street, then make a right onto Maryland Ave. Remember how I said to keep your eyes open for cool shops? This road has one of the cutest bookshops on it! The Old Fox Bookstore looks like a small shop, but upon entrance, you’ll find it’s got a big personality. It has a smell of books and the atmosphere of cozying up with a blanket and staying there all day. For coffee lovers, there’s a cafe in the back featuring very unique blends. Downstairs you’ll pass Harry’s room to find more books and a few chess sets to play.

The small 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 blind date book basket – where the books are wrapped so you can’t judge them based on the cover but rather a short description. The best part though – the garden in the back. A knight greets you before heading down into the seating area that has a chandelier as well as a small clubhouse for kids.

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

Fun Fact: The house passed through a few families only to find it’s way back to the great-grandson of the original architect, who married the daughter of the owner.

Head back toward the Old Fox Bookstore and continue on Maryland Ave toward the Maryland State House. The State House boasts an impressive history – it’s the oldest U.S. state capitol in continuous legislative use dating back to 1772. Tours are given daily. You can see a statue of George Washington in the State House as well.

Weekend Getaway in Annapolis Stop: Maryland State House
The Maryland State House is a must-see when visiting Annapolis!

Fun fact: George Washington resigned his commission here.

Annapolis Lobster Roll
Lobster Roll – an icon of Annapolis! We recommend Mason’s. Below: Lobster mac & cheese!

Continue around the grounds of the State House toward the Annapolis Circle, also known as St. Anne’s Circle for the Episcopal Church on its grounds. The circle connects most of the city and is surrounded by shops and restaurants. Rams Head Tavern and the Reynolds Tavern & 1747 Pub are just off the circle. Please note that the Reynolds Tavern sometimes has afternoon tea – so you may walk into a group of very fashionable women drinking tea and eating small sandwiches (yes – it was quite a surprise going in for a beer!) It’s up to you where you want to eat but there are plenty of places to please the palette on Main Street. There’s also plenty of shopping!

Whenever I’m in a seaside town, I have to go for fresh seafood and we absolutely LOVED Mason’s Famous Lobster Rolls. They’re famous for a reason! Spencer got a lobster roll and I got lobster mac and cheese because…. Mac and cheese. I think what we both really enjoyed about Mason’s is the simpleness of it – no gimmicks, no fancy garnishes, just lobster – oh, and butter.

The outside of Mason's Famous Lobster Rolls - one of the best places to eat in Annapolis!
Outdoor seating at Mason's Famous Lobster Rolls

If seafood isn’t your thing, there’s the Treaty of Paris restaurant, Joss Cafe & Sushi Bar, Castlebay Irish Pub and a lot more options for you nearby!

For an afternoon break and drink – stop by the Red Red Wine Bar (who serves more than just wine!). Our server was fantastic – not only was he knowledgeable about wine, but he was funny and personable as well. Once you’re ready to keep walking, continue down Main Street. I was a bit full from the lobster roll, but there are ice cream and Uncle Bob’s Fudge Kitchen for those who have a sweet tooth.

Afternoon cocktail break during our weekend getaway to Annapolis
Me and Cass during our afternoon cocktail break during our weekend getaway to Annapolis
Afternoon cocktail break during our weekend getaway to Annapolis

We enjoyed our wine and the boys enjoyed their cocktails – but everyone enjoyed the AC!

There’s a small park between Main Street and Market Space where there is live music to be enjoyed. The Kunta Kinte Memorial is not too far from this park. The original plaque that was placed in the 1980’s was quickly removed by the KKK. Annapolis did participate 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 movie Roots. Now there’s a foundation to teach heritage and embrace differences.

We took a break to freshen up at the Air BnB before heading to dinner at the Federal House in downtown Annapolis. While I couldn’t deny myself a crab dip appetizer, there’s plenty of delicious dishes including vegetarian, vegan and gluten-free! The restaurant is also dog-friendly with outdoor seating and a Doggie Menu! Established in 1830, The Federal House is also a place of history!

We ended our night at Harvest Bar across the street for some fun Saturday night karaoke!

Where to eat & drink in Annapolis

There are many places to eat during a weekend getaway to Annapolis – so here’s my recommendations off of where we were able to eat.

  • Sofi’s Creperie – 1 Craig Street
  • Rams Head Tavern – 33 West Street
  • Reynolds Tavern & 1747 Pub – 7 Church Circle
  • Mason’s Famous Lobster Rolls – 188 Main Street
  • Red Red Wine Bar – 189 B Main Street
  • Uncle Bob’s Fudge Kitchen – 112 Main Street, Suite 1
  • Federal House – 22 Market Space

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Have you done a weekend getaway to Annapolis? Let me know what you love about the city below.

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