The Ultimate Weekend Guide to Annapolis, Maryland
From the brick-paved streets to the waterfront shopping, Annapolis, Maryland is so charming and full of American history that it should be on your “Must Visit” list if you’re ever on the East Coast. And since Annapolis is less than an hour away from Washington, DC, visiting this waterfront town makes a perfect weekend getaway. We recently visited Annapolis for a quick babymoon before baby #2 comes and had an amazing time in just 2 days! Continue reading to get the ultimate guide on how to fill your weekend with what to do, eat, and stay while you’re in Annapolis, Maryland!
What to Do
Annapolis is such a walkable town that you can park your car once and spend the whole day discovering the charming streets and historical buildings all by foot. Here is a list of things to do in Annapolis, so you can pick and choose what entices you.
Take a Trolley Tour
Taking a Discover Annapolis Trolley Tour is the best way to get to know the town of Annapolis, all within one hour! Then you can finetune the rest of your weekend itinerary depending on what interests you from the tour. In one hour, you’ll learn all about the role Annapolis played in our country’s history while gazing at the most spectacular historic buildings. Did you know that Annapolis is home to the largest concentration of Georgian homes in America? Tickets are available online or on a walk-in basis and trolleys depart daily from April through October from the Visitor’s Center.
Stroll down Main Street
You cannot come to Annapolis and NOT take a stroll down Main Street. From unique boutique shops to delicious restaurants, you can spend hours walking up and down the brick-paved sidewalks. If you’re walking from Church Street, Main Street ends at City Dock, where you have an excellent view of Ego Alley and the parading boats. This is a great place to grab a meal outdoors, sunbathe on one of the benches on the dock, or even take a boat tour!
Cruise the Chesapeake Bay
Speaking of City Dock, this is where you can hop on a boat tour to explore even more of Annapolis’ history from the beautiful Chesapeake Bay! Watermark has the perfect 40-minute narrated cruise that allows you to sit back and relax, enjoying the view and the wind in your hair. Check the website for the schedule, but in the spring and summer, tours depart every hour on the hour.
Naval Academy
As you’re walking through Annapolis, you may see groups of young men and women in uniform. This is because Annapolis is home to the United States Naval Academy (USNA), which was established in 1845! And did you know that the USNA is open to the public? If you’re a history buff, you can easily spend a few hours touring the USNA Museum or taking a guided tour to learn fun and unusual facts about midshipmen. Even better, the USNA is within walking distance to Main Street (less than 0.5 mile!), so it’s easy to visit one of Annapolis’ longest standing institutions.
William Paca House
Another historic landmark that calls Annapolis home is the William Paca house. This Georgian mansion was built by William Paca in the 1760s, who was one of Maryland’s four signers of the Declaration of Independence and the state’s third governor. Step away from the bustling city and retreat to the William Paca house and gardens, which are sprawled over two acres. On a guided hour tour, you’ll get an insider’s look at how the 19th century elite lived, from the plush furnishings to the historic paintings. After the tour, take a stroll in the immaculate gardens, where butterflies flutter from flower to flower and the tall hedges make it hard to believe that you are actually in the middle of Annapolis!
Maryland State House
The Maryland State House is definitely worth a visit while you’re in Annapolis. Just steps from Main Street, the Maryland State House is the oldest state capitol in continuous legislative use in the US and is even the ONLY state house ever to have served as the nation’s capitol! Thus, it was in the Old Senate Chamber that General George Washington came before Congress in December 1783 to resign his commission as commander-in-chief of the Continental Army. Just weeks later, Congress ratified the Treaty of Paris in January 1784, formally ending the Revolutionary War! You can just feel the amount of important American history that took place at the Maryland State House as your steps echo through the marble-filled hallways.
Great Frogs Winery
While the Great Frogs Winery is not quite within walking distance of downtown Annapolis, it is still a short drive away and a great escape for a few hours. Great Frogs Winery focuses on small-batch production of their artisan-crafted wines. All tasting experiences are by reservation only, so be sure to check the website to book. Reservations allow for a seated tasting experience in a small and intimate setting. Spending a few hours at Great Frogs Winery is a wonderful way to add a slower-paced activity to an otherwise fun-filled itinerary!
Where to Eat
While there are tons of unique options for places to eat in Annapolis, here are some MUST VISIT places that are iconic to the charming city.
Miss Shirley’s
One of your weekend days must absolutely start with a breakfast or brunch date at Miss Shirley’s. Be forewarned – there will be a line as they don’t take reservations. But trust me, that line is worth it. Less than a mile’s walk from Main Street, Miss Shirley’s serves traditional southern flare for breakfast, brunch, and lunch while also using local ingredients from the Chesapeake Bay region of Maryland. They were even featured on Food Network’s Diners, Drive-Ins, and Dives! We had one of their specials of the day – a stack of pancakes stuffed with pulled pork and cheese ????. We also shared Shirley’s Affair with Oscar, which is a 5 oz. Black Angus Filet topped with jumbo lump crab meat and hollandaise and voted Best Breakfast Dish in Maryland by Food