weekend in Annapolis Maryland

How to spend the weekend in Annapolis Maryland

We spent the weekend in Annapolis Maryland and was totally surprised at how charming this little town is.  I don’t know why it took us so long to visit l, but I’m sure glad we did. 

Annapolis is one of the oldest cities in the U.S. and served as the nations Capitol before it was moved to Washington DC! It’s such a quaint little town, full of history and a relaxed vibe, with its location by the Chesapeake river. 

 On the blog I highlight some of the top things to do in Annapolis, so you can plan that weekend getaway to Maryland.

weekend in Annapolis Maryland

Top things to do in Annapolis Maryland

Check out the Visitors Center in Annapolis

Your first stop on your weekend in Annapolis Maryland should be the Visitors Center. This is where you can get more info on what to do and see in Annapolis, and where you can sign up for the Annapolis Trolley tour. This one hour tour takes you to all the must sees in the city!

If you are driving in, you can find parking at the Gotts Court Garage located just behind the Visitors center, which is just a short walk away to the historic center. There are also metered parking spaces on Main Street, and a few other parking garages around the city.

weekend in Annapolis Maryland

Recommended Annapolis Tours:

Best time to visit Annapolis

I’m sure Annapolis is beautiful in any season. But springtime is the start of all the city’s great festivals and events. We happened to visit during the annual Sailboat Show and Earth Day & Spring Festivities and it was so much fun.

 The Annapolis Spring Sailboat Show is held each year at the City Dock. You will find sailboats on display in the water and on land. If your in the market for a new boat, you can even purchase one on the spot!

weekend in Annapolis Maryland

The annual Spring and Earth day festival is held on the historic streets on Maryland Ave. This event celebrates earth day, and the spring season with some live music, a farmers market and food, as well as some kid friendly crafts and activities.

weekend in Annapolis Maryland
Spring and Earth Day festival

Go on a cruise on the Chesapeake 

Known as the sailing capital of the U.S., one of the best things to do here is to go on a cruise. 

There are so many cruises to choose from, you can sail the Schooner Woodwind on the Chesapeake, or go sailing on a pirate adventure with the kiddos!

weekend in Annapolis Maryland

Take a stroll through Main Street 

 A stroll through Main Street is definitely one of the highlights of our visit to Annapolis. 

This red brick street is home to some of the best restaurants in the city, and is also a great place for some retail therapy with it’s many local shops and art galleries. 

weekend in Annapolis Maryland
weekend in Annapolis Maryland

Explore the history in Annapolis 

There is so much history to explore on your visit to Annapolis. Its historic district includes 18th-century brick houses and the domed 1700s Maryland State House, where George Washington resigned his post as Commander in Chief of the Continental Army. 

weekend in Annapolis Maryland
Views of the U.S. State House from Main Street

Maryland State House 

Make sure to visit the Maryland State house. It is the oldest U.S. state Capitol in continuous legislative use, dating to 1772, and once served as the capital of the United States of America, before it moved to DC.

The State House is also the place where the Continental Congress met from November 1783 to August 1784, where the Treaty of Paris was ratified, and where George Washington resigned as Chief of Commander of the Continental Army. There is an exhibit that you can visit and is absolutely free to enter. 

weekend in Annapolis Maryland

Tour the US Naval Academy

Annapolis is also home to the United States Naval Academy. You can take a guided tour of the “Yard” as they call it, and explore the grounds and learn more about the U.S. Navy’s history in Annapolis.

weekend in Annapolis Maryland

Stroll through the historic streets of Annapolis

If you’re a history buff, Annapolis should definitely be on your list of places to see. Not only did Annapolis serve as our nation’s first peacetime capital, it was also home to Maryland’s four signers of the Declaration of Independence. 

You can visit their homes, which are just a few minutes walk from each other. One in particular is the William Paca house and gardens. You can go on a guided tour of this 18th century Georgian mansion and experience what life was like back then!

weekend in Annapolis Maryland
William Paca House

At the nearby Pinkney street, you can visit Hogshead house, which is the perfect example of a building type that was common in 18th-century Annapolis. 

Admission is free and you can learn more about how the “everyday people” lived back then, with guides dressed in colonial attire, and the opportunity to see and handle authentic and reproduction artifacts.

weekend in Annapolis Maryland
Beautiful Row Houses on Pinkney Street
weekend in Annapolis Maryland
The Shiplap house is one of the oldest buildings in Annapolis. Built around 1715, the house was used as an inn and Tavern back in the day.

Fun things to do in Annapolis with kids

Painting Pottery at Clay Bakers

Annapolis is fun for the whole family. Located on Main Street is Clay Bakers, take the kiddos here for some pottery painting fun. We had a blast painting tiles, and you can have your masterpieces mailed to you when you are done!

weekend in Annapolis Maryland

Visit the Old Fox Books and Coffeehouse

There is also a cute little bookstore that the kiddos will absolutely love. The Old Fox Books and coffeehouse is the perfect place to hangout. It’s one of the coolest bookstores we’ve come across, and the kids will love the outdoor garden complete with a fairytale cottage!

weekend in Annapolis Maryland
weekend in Annapolis Maryland

Where to eat in Annapolis 

Annapolis has a great food scene, serving some of the most delicious food we’ve tasted! Here are a few of our favorite places to grab a bite!

Iron Rooster– If your a breakfast lover, then head over to the Iron Rooster. They serve some of the most unique and amazing breakfast choices in the area. We especially loved the Crab hash and French toast. For a lighter option, the strawberry avocado toast was to die for!

Make sure to ask for their homemade pop tarts. They aren’t listed on the menu, but taste so amazing and come in a few different flavors.

weekend in Annapolis Maryland
Yummy house made Berry RoosTart at Iron Rooster

The Red Bean-The Red Bean is the best ice cream/coffee shop in the city. You can create your own custom ice cream, with many flavors and toppings to choose from. One of my faves was the affogato, which consisted of vanilla ice cream topped with espresso, so yummy! 

weekend in Annapolis Maryland

Chick and Ruth’s Delly– Chick and Ruth’s Delly serves breakfast all day long as well, but is known for their famous crab cakes. The crab cakes here are some of the most delicious we’ve ever tasted and they’re huge!

weekend in Annapolis Maryland

Annapolis Market Square– This is the best place to eat if your indecisive about what to eat! They have everything here, from the freshest seafood, to burgers, pastas and fresh salads. 

weekend in Annapolis Maryland

Where to stay in Annapolis

There are so many options of places to stay when visiting Annapolis. There are a few hotels in the area, as well as bed and breakfasts and historic inns. Make sure to reserve in advance as they’re usually sold out. 

We love the Graduate Annapolis Hotel. It’s located just a short walk away from the historic center, and it’s such a beautiful hotel. The Hilton Garden Inn Annapolis is also a great option when visiting Annapolis. It’s located further from the historic center, but it’s just a short drive away.

Recommended Annapolis Hotel:

weekend in Annapolis Maryland
The Academy Bed and Breakfast in Annapolis

These were just some of Annapolis main attractions, there’s still so much more to discover on your visit. Just a short drive away is Maryland’s World War II Memorial, and Sandy Point State Park, if you want to spend some time by the water, with views of the Chesapeake Bay bridge.

We spent the weekend in Annapolis, but you can easily most of the main sights on a day trip. Plan that weekend getaway to Maryland and explore this charming little town!

Read more about our visit to some of the most historic places in America here!

weekend in Annapolis Maryland
World War II Memorial
weekend in Annapolis Maryland
Sandy Point State Park


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