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.
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.
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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.
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, plus Annapolis looks so much more beautiful when all the spring flowers are in bloom!
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!
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.
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!
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.
Explore the history in Annapolis
Maryland State House
Make sure to visit the Maryland State house on your visit to Annapolis. There is an exhibit that you can visit and is absolutely free to enter.
The Maryland State House 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.
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.
Stroll through the historic streets of Annapolis
If you’re a history buff, Annapolis should definitely be on your list of places to see.
There is so much history to explore on your visit to Annapolis. Take a stroll and explore the historic district, which includes 18th-century brick houses that looks so charming.
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!
Fun things to do in Annapolis with kids
Visit Hogshead 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.
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!
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 take a sightseeing break.
It’s one of the coolest bookstores we’ve come across, and the kids will love the outdoor garden complete with a fairytale cottage! Grab a cup of coffee and enjoy the the outdoor seating, while the kids enjoy the outdoor play area.
Pirate Adventures on the Chespeake
Set sail with Pirate Adventures on the Chesapeake. This is one of the best family attractions in Annapolis.
Let the kids live out their pirate fantasies as they go on a sailing adventure.
They will love firing water cannons and go in search for sunken treasures. It’s a fun day out for the whole family! Tickets costs $28, $14 for kids 2 and under.
Visit Sandy Point State Park
On your visit to Annapolis, make sure to visit Sandy Point state park for some fun in the sun.
This 786 acre park has a beach with breathtaking scenic water views that overlook the Chesapeake Bay and bridge.
The park also offers accessible food and beverage concession, fishing, picnic areas, shelters, bathhouses and playgrounds. It’s a great place to add to your itinerary when planning a visit to Annapolis.
More ideas in Annapolis for kids:
–Annapolis Maritime Museum-Learn about the Annapolis area’s maritime heritage and the ecology of the Chesapeake Bay through programs, exhibits and community events.
–The Chesapeake Children’s Museum
-Quiet Waters Park
Visit the World War 2 Memorial
Visit the Maryland World War 2 Memorial that honors the brave men and women who gave the ultimate sacrifice for our Nations freedom.
The memorial is located just a short drive from Annapolis, along Route 450 overlooking the Severn River.
The Memorial consists of a rectangular amphitheater surrounded by columns and granite slabs inscribed with the names of 6,454 Marylanders who died in World War II. Stone panels and mosaic circles further depict Maryland’s role in the War.
Christmas in Annapolis
One of the best times to visit Annapolis is during the holidays when the city gets all dressed up with festive holiday lights and decor.
Christmas in Annapolis is just so beautiful and there are so many fun holiday events going on.
One event we look forward to in Annapolis is the Eastport Yacht Club Lights Parade. Watch the boats as they make their way along the Chesapeake all dressed up in holiday decor.
You can also look forward to the Chocolate Binge Festival, as well as the city’s Tree Lighting Festival. Make sure to visit the website for all the fun holiday events in Annapolis.
*Read our blog on some fun Christmas Getaways from Washington DC. I share the best day trip ideas during the holidays.
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.
- 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!
- 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!
- 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.
More Restaurant options
- Galway Bay Irish Restaurant
- Preserve
- Mason’s Famous Lobster Rolls
- Cafe Normandie
- Buddy’s Crab and Ribs
- Vida Taco Bar
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.
- Graduate Annapolis Hotel– This is one of our favorite hotels in Annapolis. It’s located just a short walk away from the historic center, and it’s such a beautiful hotel.
- Hilton Garden Inn Annapolis– Another great hotel option when visiting Annapolis. It’s located further from the historic center, but it’s just a short drive away.
- Annapolis Waterfront Hotel– Stay in this waterfront property, located in the historic district and close to all the main attractions.
Recommended Annapolis Hotel:
Booking.com
These were just some of Annapolis main attractions, there’s still so much more to discover on your visit. 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!
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