19 THINGS TO DO IN ANNAPOLIS, MD YOU CAN’T MISS

Come to one of the oldest towns in America and experience culture, history and a whole lot of crab when you visit Annapolis, Maryland! Once the original capital of America, this town’s significance dates back to 1649, and it’s located less than an hour from Washington DC. With plenty of stories and activities for all, Annapolis is the place to be and see. 

Wander through the old cobblestone streets, admire the colorful row houses, and walk the grounds of the Naval Academy. Whether you’re eating ice cream by the water or going for a delicious seafood meal, look out for sailboats on the horizon and lively locals all around you.

Fall in love with this historic town, enjoy its riveting history, and get ready to eat Old Bay seasoning with every meal! Here are 19 things to do in Annapolis that you’re not going to want to miss. 

19 THINGS TO DO IN ANNAPOLIS, MD YOU CAN'T MISS

WILLIAM PACA HOUSE & GARDEN

The William Paca House & Garden allows you to visit the home of patriot leader, William Paca, who signed the Declaration of Independence in 1776. Paca was the 3rd governor of the state of Maryland and lived in this home with his wife and children. 

With guided tours available, learn a piece of American history and see pieces of Paca’s life. In the small and charming town of Annapolis, the Paca house has quite a nice size garden with well-groomed paths and lush grass. Look into the small pond for lilies and frogs, while admiring this historic landmark.

ANNAPOLIS MARITIME MUSEUM & PARK

Head over the bridge into the gorgeous neighborhood of Eastport and learn about Annapolis’s maritime past on the Chesapeake Bay with a visit to the Annapolis Maritime Museum & Park. Discover the importance of oysters in the Bay and how they are cleaning the water system. 

This small museum gives you great insight on the Chesapeake, which is a huge part of Annapolis living. If you have the chance to hop on an informational sailing voyage, I highly suggest the Skipjack. The museum and captains are very knowledgeable, and this experience allows you to see the museum from the water. 

BANNEKER-DOUGLASS MUSEUM

Learn about the life of Frederick Douglass, a born slave in Maryland, and Benjamin Banneker, born free in Maryland, and discover their contribution to African American History during your visit to the Banneker-Douglass Museum. This small museum shows how Banneker, Douglas and many others fought for equality throughout their life. 

This museum honors the legacy of important African Americans activists, and is here to promote their culture and history. Easily spend a few hours wandering the informational exhibits while touring Annapolis, MD. I also highly recommend watching the short videos, as they provide a deeper understanding of African American history. 

US NAVAL ACADEMY MUSEUM

GO NAVY! Walk the historical grounds of the US Naval Academy and come across this engaging museum focusing on the sea and progression of the Navy. Discover two floors of enriching facts and stories, through people and artifacts that highlight the importance of the Naval Academy and Navy!

From the Revolutionary War to the modern-day fleet, understand how the Navy works and how the graduates have led their fleets around the world. From modern collections and smaller replicas to intricate illustrations on display throughout the museum, learn about the great Navy and its historical significance. 

PIRATE ADVENTURES ON THE CHESAPEAKE

All Hand Hoy! Come aboard a pirate ship and sail in Annapolis where children will search for adventure and discover the ways of pirate life. Search for treasure, fire water cannons and get ready to Aaaarrrrgggghhhh your way through the Chesapeake on a trip with Pirate Adventures on the Chesapeake.

This memory will be remembered for a lifetime! From face makeup, bandanas, eye patches and lots of props, children will feel like pirates of the sea and have the best time ever! Children will be dressed to pirate success, and this is an exciting way to interact with others and be out on the water. I highly suggest eating after at one of the fabulous restaurants in Annapolis. 

CHICK & RUTH’S DELLY

Chick and Ruth’s is an iconic Annapolis institution that has to be eaten at and experienced in all its glory. Be prepared to wait, as this is one of the most popular places in town for locals and tourists alike. While you wait, wander Main Street and get ready to dig into an unbelievable menu, with options for all and flavors that are drool worthy.

From its jumbo lump crab cakes to its creamy chipped beef, enjoy a spectacular meal at this beloved restaurant. Visit in the morning at 8:30 on the weekdays and 9:30 on weekends for the Pledge of Allegiance, then sit down with a diverse group of people ready to enjoy fresh, delicious, and homemade food! 

A meal here is one of the best things to do in Annapolis!

THOMAS POINT SHOAL LIGHTHOUSE

Visit one of the coolest lighthouses in Maryland and see for yourself why this secluded light brings so much wonder. Set in the Chesapeake Bay at the mouth of the South River sits the last screw-pile lighthouse in the Bay — Thomas Point Shoal Lighthouse. Reached by boat only, this adventure is waiting for you!

With guided tours available on select dates in the summer, cruise the bay and stop off at the lighthouse for a tour. Walk inside the screw-pile lighthouse and see old fixtures, the light and its amazing architecture up close, then enjoy a leisurely boat ride back to Annapolis. 

Tip: Please book ahead of time and wear closed-toe shoes! 

QUIET WATERS PARK

With beautiful trails, parks, and lush green space, Quiet Waters Park is the perfect place to relax and go for a calm and peaceful afternoon. Bring your bikes and lunches and enjoy 340 acres of beautiful park land, with both forests and water. Whether you take a stroll along the water’s edge or admire the large water feature in the park, this is a great place to spend time with family and friends. 

Here you’ll find boat rentals — you can rent kayaks, canoes, and paddle boards and roam the quiet waters of the South River for an unforgettable and tranquil experience. See the park from the water and find small water ways, searching for fish and crabs! 

FORT MEADE NSA CRYPTOLOGIC MUSEUM

Test your cryptology levels and see how important this museum is to the nation’s history. Learn about coding, the different techniques and important coding machines throughout time. From the enigma machine during World War II to present day, see it all at the NSA Museum! 

Coding has been used to decipher messages, secure communication, and protect against attacks. Its uses vary, but the results can save lives and should be seen today. With artifacts, shared stories and technology throughout, the NSA Museum deciphers the world of codes. 

THURGOOD MARSHALL MEMORIAL

Thurgood Marshall was one of the leaders in the fight for equal Civil Rights, and as a native Marylander, he is cherished by many. As the first African American appointed to the Supreme Court, Marshall has had a huge part in America’s History as well as Maryland’s. 

The Thurgood Marshall Memorial statue is outside the Annapolis State House and honors his great life. Easily view this impressive statue before or after touring the Annapolis State House, or make a special stop just to see it.

EGO ALLEY

Head to the heart of Downtown Annapolis and meander along the edge of Ego Alley. Watch as boats come into the Annapolis Harbor and marvel at the impressive boats lined up against the walls of the alley. Pick up some ice cream and sit along Ego Alley for a moment while enjoying life. 

Take a water taxi or simply people-watch from Pussers Caribbean Grill into the life of the bay through the Alley! From huge yachts to simple little sailboats, be amazed by Annapolis and stop in some shops and restaurants for good food and a good time.

MARYLAND STATE HOUSE

Stroll the cobblestone streets of Annapolis and find the impressive Maryland State House! Many have walked the halls of the state house, including George Washington, who came before Congress to sign the Treaty of Paris, which ended the Revolutionary War and surrendered his authority as commander-in-chief of the Continental Army.

This is the only state house that has served as the nation’s capital and was also the nation’s first Capital. Full of history and significance, this building relishes in America’s thrilling past and gives a nod to the future! 

SCHOONER WINDWARD

Get ready for the races! Throughout the summer, enjoy the Wednesday Night Races, where sailboats take the bay in a thrilling race against all. Watch as boats flock to the scene and spectators look on as to who has sailing bragging rights for the week! 

As the sun sets and the weather becomes cooler, look on and cheer for boats or book a cruise for yourself on the windward and get out onto the bay. It’s a thrilling experience and the views are beautiful. 

Tip: I highly suggest going to the Boatyard Bar and Grill in Annapolis after the races for food and drinks.

CRAB & OYSTER TRAIL

Oh Shucks! Get ready for flavors, fun and a whole lot of crabs and oysters on this lively and delicious trail tour! From eating at some of the best seafood restaurants in all of Maryland to experiencing the joy of seafood markets, Annapolis has some of the best around!  Experience the Maryland Crab & Oyster Trail and discover why Annapolis is famous for its crabs and oysters.

For an authentic, delicious and unique meal, head over to Cantler’s Riverside Inn! See the fisherman bringing in crabs and get cracking. Have a bushel on the table and start enjoying some of the best crabs in all of Maryland. From crabs, oysters to ice cold drinks, try seafood the Annapolis way and never go back! 

Remember to always use Old Bay Seasoning. (It’s pretty much required!)

WATERMARK CRUISES

Get the full Annapolis experience on a Watermark Cruise! Hop on at the Annapolis Harbor and get to know the Chesapeake Bay a little better. From short informational cruises to day-long experiences, see the sights and have good old fashioned fun. With plenty of options and excursions to suit your fancy, this is your one stop shop for water and land adventure.

Looking for walking tours too? They have you covered. Get to the roots of Annapolis’s deep and enriching history with a colonial tour of the Maryland State House or the Naval Academy through stories and evidence.

HISTORIC LONDON TOWN AND GARDENS

With 23 acres of parks and gardens to explore, take to London Town to see native plants, wildlife and unbelievable scenery. With history, horticulture, and archeological findings, a quick trip to this landmark will sure be one for the books.

Walk in the William Brown House, built around 1760 and see for yourself this impressive Georgian House. See who lived at the home, worked at it, and how it became an important aspect of London Town and Maryland Life. 

SANDY POINT STATE PARK

Put on your sandals, grab your beach chairs, and pack your coolers for Sandy Point State Park. Swim in the cool water of the cherished Chesapeake Bay and look out on sailboats and fast powerboats under the bay bridge. Fish off the shores, have picnics at the tables, and play games on the soft sand during an exciting beach day!

If you come in the summer, bring lots of water, as Maryland can get quite warm and humid. In the winter, Sandy Point hosts Lights on the Bay, which cannot be missed, and they also have the ever-popular Polar bear Plunge.

THE KUNTA KINTE – ALEX HALEY MEMORIAL

Drive or walk past the Kunta Kinte-Alex Haley Memorial. This charming and unique creation by Alex Haley near City Dock in historic Annapolis, MD is where you can feel inspired and find truth in the meaning of Haley’s art through his vision of racial reconciliation and healing. It is to honor African ancestors, and people around the world who have lost their voice. 

Designed to preserve cultural heritage and society, Haley’s impressive and striking sculptures can be seen by all who visit Annapolis. Easily sit among them, or simply walk by during a tour or by yourself and admire this great part of Annapolis.

THE HAMMOND-HARWOOD HOUSE

Step inside the Hammond-Harwood House and feel like you’re stepping back in time.

Open for tours, the home was built in 1774, and was the final work of acclaimed architect William Buckland. During your tour, you will learn more about the history of the families and the enslaved people who lived in the home. Discover information about the architecture and artwork, as well.

Featuring carved doorways and beautifully-decorated formal rooms, this home is on the National Register of Historic Places. Several different types of tours are offered daily.

MORE INFORMATION FOR YOUR TRIP TO MARYLAND

WHERE TO STAY IN ANNAPOLIS

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