Why Spending a Day in Annapolis, Maryland Should Be on Your Next To Do List

Kids like water. Fact. Even if they don’t like being in it, they like looking at it. And when looking at it also includes looking at sailboats and pirate-esque ships, they like looking at it even more (unless they are scared of pirates, which is a completely valid fear). What I’m getting at is that Annapolis, Maryland, perched on the Chesapeake Bay at the mouth of the Severn River is bound to be an amazing experience for little people based solely upon location (but believe me, that is far from all this quaint little city has to offer…there’s ice cream…oh is there ice cream (stares dreamily out into distance)).

Beyond just ice cream and water though, this city has oodles to offer a family. And with a rich history, it has had years to perfect its hospitality and tourism related industries. Whether you come prepared with an itinerary or just decide to swing by at the last minute, it won’t be hard to figure the city out and maximize your time there. They make it easy. And every family needs a day that’s easy now and then. So what makes this city, home to approximately 38,500 people, standout (other than the fact that it’s where I got married…and the ice cream)?

The Layout

If given the choice between driving from place to place and digging my little people out at every stop and then strapping them back in to get to the next or just getting them out once, grabbing a stroller, and heading out for the day, I would much prefer option B (three carseats across a back row makes for less than stellar moments buckling littles in…in fact, it may actually be the source of a number of parent arguments, sweaty brows, pinched fingers, and angry groans…). Anyway, what makes Annapolis a fantastic place to be is that the entire city can be covered by foot after parking just one place. With street parking, metered parking, and 16 parking garages located throughout the city, it can be fairly easy to find somewhere to park. Even with those spaces available, it’s important to know if there are any events happening in the city itself or at the Annapolis Navel Academy because that can drastically alter the parking situation. (A guide to city wide special events can be found here and a guide to special events at the Naval Academy can be found here.)

As the literal first beautiful day of Spring in the region, we happened into Annapolis in the early afternoon on what was a crowded day. Oh yeah, it was Easter too, so the Naval Academy was having their Easter Brunch, which was taking place just as we got to town (admittedly not well planned on our part as we had meant to get there earlier in the day but…well…kids). Needless to say we had to drive around for about 10 minutes through traffic before we found a parking spot along a side street right off the main road. It was easy peasy. And the town is so navigable by car, that it wasn’t stressful to move through the crowded streets.

Once we got out of the car, the movement of people and the pull of the water made it easy to find the main street. Beyond just those markers though, the city itself is laid out in a way that anyone can handle. In the late 1600s, it was designed by Sir Francis Nicholson to emulate the capitals of Europe, so the streets radiate out from two main circles, both of which highlight important structures: the once spiritual center of the city, St. Anne’s Episcopal Church (The Church of England) and the State House or the seat of government, the political center of the city. This use of two circles with streets then connecting to the water makes Annapolis a walkable city, perfect for tiring out a gaggle of little people.

The History

Annapolis has always been a cultural hub from the moment Royal Governor Sir Francis Nicholson first chose the location as the provincial capital of the Maryland royal colony in 1694. At that time, it was known as Anne Arundel’s Towne, but he renamed it Annapolis, in honor of Princess Anne of Denmark and Norway, the eventual Queen of Great Britain. While initially little more than a village, the location of Annapolis marked it for greatness as it grew into a political and cultural center, an important port of entry, and an important commercial port as well as a leader in water-related industries such as oyster-packing, ship building, and sail-making. Sure, all of this historical info is great, but why do I bring it up? Because Annapolis is a city that has not lost that deep connection to its past.

This little city is a city that ranks top in a number of significant ways. These walkable streets currently are home to more original 18th century structures than any other city in the United States. Some of these homes were those of prospering merchants who wanted to emulate their homelands in the colonies, so they built lavish mansions where they hosted important social functions (many of which were attended by the Founding Fathers of United States). Fortunately, walking tours through the city are bountiful and some of these homes are open to the public to tour (check ahead for closings or events), including the Paca House and Garden, an 18th century mansion constructed by William Paca, one of the signers of the United State’s Declaration of Independence. Annapolis is also the location of the first theater in the new world and the third oldest college: St. John’s College, founded as King William’s School in 1696.

Beyond the homes, is the State House, which was the first and only State House to serve as the nation’s capital, from November 1783 through August 1784. During this time, General George Washington resigned from the Continental Army in this building in 1783. It is also where, on January 14, 1784, Congress ratified the Treaty of Paris, ending the American Revolution. And now, it is the oldest state house in continuous legislative use (and one that can be toured!).

Finally, the Naval Academy, founded in 1845, is of significant historical relevance (not to mention it has a great location in the historic waterfront downtown area). Not only is the campus, or Yard, open to the public, it also offers in-depth guided tours to the public. Beyond tours though, the on-site U.S. Naval Academy Museum chronicles the historic landmark as well as the Navy itself. It holds salvaged artifacts and tells stories of battles and events that took place throughout the Navy’s history. Perhaps the most intriguing part of the visit to the Naval Academy is seeing the remains of Commodore John Paul Jones, the navel leader of the American Revolution. His body, discovered in 1905 in France, finally made its way to its final resting spot at the Naval Academy in 1913. Now they remain in the crypt under the Naval Academy’s Chapel. (Intriguing, right?)

The Art

It should come as no surprise that a colonial town that was home to the first theater in the new world continued to embrace the art scene in the new world. Because of the desire to emulate their old country, not only did the colonialists build their exquisite homes with a nod to their old countries, they also wanted to decorate them this way as well. This means that renowned portraitists, including Charles Wilson Peale, were employed in the town, capturing the likenesses of its inhabitants.

Today though, the city is much more than a theater and portraitists. While the city is currently home to a number of theaters, the downtown streets are also littered with galleries; in fact, the greater Annapolis area is home to more than 23 galleries, not to mention the exhibits hanging around town in restaurants, stores, and any other available space. Given its location, it wouldn’t be difficult to assume that Annapolis’ art is predominately marine art, but a quick walk through town will prove otherwise. Art here isn’t confined to one medium, one subject, one style, or one price. If this seems disappointing, don’t fret, high quality marine art can still be found at the Annapolis Marine Art Gallery.

Art in Annapolis isn’t just found in galleries and exhibits. The city hosts a number of festivals throughout the year as well designed to highlight this aspect of the city’s identity. For example, the city has The Annapolis Film Festival, First Sunday Arts Festival, Paint Annapolis, and the Annapolis Arts & Wine Festival, among other events occurring throughout the year. This is, again, why it’s important to check with the city’s list of events to time a trip correctly.

The Water

If it’s water you want, head to City Dock. We found it relaxing to just grab a seat (with ice cream in hand) and watch all the ships and people move on by us. The water is the hub of the city, and it’s clear why. There is so much activity going on surrounding it, and even without owning a boat, it’s quite simple to take advantage of the location. Stop by the Kunta Kinte-Alex Haley memorial that commemorates the 1767 arrival of Kinte, a slave that became the subject of Haley’s book Roots. This sculpture of Haley reading from his book to a group of children is located at the head of City Dock, surrounded by Annapolis’ downtown.

Beyond just strolling along the water and the stores that line it, there are a number of historic boat tours that depart from city dock and other close by locations. There are regular cruises on the Chesapeake Bay as well as cruises aboard schooners. And, for the exceptionally brave, there are also pirate adventures to be had. That’s right. I said pirates. If being a passenger in someone else’s boat isn’t that appealing, it’s also possible to rent canoes and kayaks in the area to get out and explore the Chesapeake. Annapolis also has plenty of opportunities to get out on the water and learn how to sail or go fishing (though the commitment for either of these may be a bit more than I could ever make with my three little people bounding about).

Annapolis isn’t just about getting on the water, it’s also about admiring those vessels that make their home there. With a rich history in sailmaking and boat-building, Annapolis has always been a place to watch ships. This is even more so the case during Annapolis’ Annual Boat Shows, which usually take place in the Spring and Fall. There are both powerboat shows and sailboat shows, so it’s important to check ahead for dates, as the city will be both crowded and filled with energy.

The Food

As a city with something called a “Chocolate Binge Festival” I tend to believe that it is nearly impossible then to come up empty handed when looking for a good restaurant. Clearly the value of chocolate is something this city understands, which tells me that they also truly understand the plight of mothers and little people, both of which consider chocolate to be an important food group and a source of all that is good (but of course not at my house, we’re all totally organic and whole foods all the time. Every. Single. Second.). It doesn’t end here though, there is a Strawberry Festival, a barBAYq (who doesn’t love a good pun), a Restaurant Week, an Oyster Roast, Kegs and Corks, and an Oyster Festival, to name just a few of the food-related events happening in the city. Oh, and there’s the Maryland Seafood Festival. (What would a city on the bay be without a celebration of the food in the waters surrounding it?)

In a city that celebrates food, it’s pretty safe to say that the restaurants are plenty. And that they present a variety in terms of ambiance and offerings, which every parent of a little knows is extremely important as little people tend to deeply love one food for approximately one day once a month, and if that food can’t be found, well…let’s just not imagine it. Why bring ourselves down? The point is, with over thirty restaurants in the immediate area, everyone can be accommodated here (and it’s not just seafood, although the seafood is fresh and fine).

And that brings me to my final point. Ice cream. There is something alluring about an ice cream shop that has managed to delight a city of locals and tourists for over four decades. That ice cream shop is Storm Bros. Ice Cream Factory (though it’s really hard to go wrong with choosing an ice cream shop in this city). The shop opened 39 years ago, when, in 1976 two young brothers, ages 19 and 20, rented a storefront at 130 Dock Street and created the Storm Bros. Ice Cream Factory. The shop serves over 40 flavors, including sugar free and sorbet, so no matter the case, there will be something delicious for everyone (even the most particular type of little person). With these kind of credentials though, and with this kind of creamy goodness, don’t be surprised to find a bit of a line, maybe even one that extends out the door and down the street. The good part is they move fast, so that ice cream will be in your hands before you even know it. And it’s worth it. Quite worth it. (It’s like “it’s so good that getting ice cream is both the first and last thing I will do during each of my days in Annapolis.”)

Annapolis is the kind of city every traveling family needs to take a break at, whether for a day or for a few, it has a slow pace that just seems to reorient a weary traveler. It’s water. It’s food. It’s history. It’s wandering. It is everything an easy, exciting day is made of.