Maryland/Virginia 2023

Annapolis, US Naval Academy

Day 4

Last night, we were in a bit of a frenzy figuring out a destination for today. Our top candidates were originally Harper’s Ferry + Antietam, or DC. Unfortunately, there was road construction causing significant detours and delays near Harper’s Ferry. We also learned there was a huge rally scheduled on the National Mall in Washington, with potentially 60,000 people expected, plus some accompanying security concerns. So, after breakfast, we decided to head southeast instead, and drove to Maryland’s state capital, Annapolis.

United States Naval Academy

After a pleasant hour and a half drive, we arrived in Annapolis, and secured street parking near King George St. with surprising ease. Faith and I walked over to the entrance of the US Naval Academy, and rendezvoused with the Pinkertons. William, a West Point graduate, made sure all the kids had “Go Army // Beat Navy” pins to wear for the duration of our visit…plus some sported Union infantry hats from our visit to Gettysburg. For good measure, I think one was even sporting a “Go Army // Beat Air Force” pin. We made a quick stop into the Armel-Leftwich Visitor Center to register and receive visitor passes, and then began our self-guided walking tour of campus.

I should note that our “self-guided” tour was mostly led by William, who couldn’t resist making a few jabs about the superiority of his alma mater and preferred service branch. Nonetheless, he offered some excellent insight into the campus. We walked the grounds for a while, taking in the sights on the historic campus. We’d hoped to visit the museum on campus, but it was unfortunately closed for renovations.

The Naval Academy Chapel

Since the museum was closed, we headed across the terrace to the Naval Academy Chapel, a beautiful building that opened in 1908, with a 193′ tall dome. The inside is spectacular – not overly ornate, but very beautifully designed and built.

To end our tour of the chapel, we headed to the lower level to view crypt and sarcophagus of John Paul Jones, a hero of the American Revolution who is known as the “Father of the American Navy”.

After exiting the chapel, we decided it was time to find some lunch. We walked back across campus, exited through the gate, and began walking towards downtown.

Chick & Ruth's Delly

We settled on eating at Chick & Ruth’s Delly, a local diner (open since 1965) that’s famous for their colossal crab cakes and equally hefty milkshakes – ranging from 20oz up to 6lb! Before we could order, I realized that even though you could “renew” your parking in the ParkMobile app, you had to move your car to a different zone. So, I had to walk all the way back to the other side of the Naval Academy, get in the car, and find another parking spot (which was thankfully close to the restaurant).

Finally back at the restaurant, I was now extraordinarily hungry from the long walk, as was everyone else from the extended wait. The “delly” was very accommodating though, and even allowed us to take our strollers in the back entrance so we could spread out at a larger table. Faith and I split two dishes, their signature half-pound crab cake sandwich, and a seafood club on rye, which had a crab cake and shrimp salad on a triple-decker sandwich. We also ordered a side of onion rings for all of us to split.

I can say without a doubt that this was the best crab cake I’ve ever had. There was very little filler; just enough to hold together the giant lumps of sweet crab meat. Even though it was a ton of food, we ate nearly every bite, although we had to forego the bread towards the end of the club sandwich to make sure we didn’t waste any of the seafood.

Chick & Ruth's Delly
Annapolis, MD

Oversized everything, but you’ll be grateful for the excessive amount of meat in the crab cakes.

* – Would definitely visit again

** – Exceptional, must visit if you’re in the area

*** – Worth making a special trip to eat there

For more info on food ratings, click here.

Maryland State House

We cleaned up from lunch (which is quite the process with a handful of kids), and headed back out to explore a bit more of Annapolis. Walking from the restaurant up to the top of the hill, we arrived at the Maryland State House, passing many historic buildings, beautiful flower beds, and colorful trees along the way. We attempted to visit St. Anne’s Parish, a historic church dating back to 1692, but it was closed at the time.

Ice Cream // Waterfront

After walking about a mile more through the historic buildings, we decided to backtrack to the Annapolis Ice Cream Company, a spot we’d seen earlier that of course intrigued all the kids (and adults). I got oatmeal cream pie and lemon chocolate chip; Faith got oatmeal cream pie and pumpkin chocolate chip. All the flavors were excellent, especially the pumpkin chocolate chip, which Faith could not stop talking about the remainder of the trip.

Annapolis Ice Cream Company
Annapolis, MD

Excellent selection of homemade ice creams and sweet treats with some creative flavors.

* – Would definitely visit again

** – Exceptional, must visit if you’re in the area

*** – Worth making a special trip to eat there

For more info on food ratings, click here.

We took our ice cream down to the waterfront, and sat and watched the ducks and people jaunt around a section of the Annapolis Harbor known as Spa Creek or Ego Alley.

Ducks, Books, and Coffee

Once we finally tired of duck- and people-watching, we walked to Old Fox Books & Coffeehouse near St. John’s College, which was about a half-mile away. The weather was pleasant, but chilly and breezy, so it felt good to get moving again. The coffee shop/bookstore combo was an interesting place to browse, and had an excellent selection of children’s books. Faith and I split an Americano (since their drip coffee was shut down for the day) to give us a caffeine boost to stay awake for the drive home.

Maryland WWII Memorial // Bridges

We headed our separate ways back to our vehicles, and began the drive back to Havre de Grace at sunset. Faith and I saw a nice sunset over the Naval Academy Bridge, and made a quick stop at the Maryland WWII Memorial to take a picture of the colors over the water. Driving back north, we actually crossed the 1.6mi Francis Scott Key Bridge, which has since collapsed after a container ship collided with it in March 2024.


Back at the Pinkertons’ house, Anna pulled together a light charcuterie selection for dinner. We made more affogatos with the ice cream I’d bought, and watched more of Gettysburg, but didn’t make it very long because we were so worn out from the day. Our feet were sore from walking on all the cobblestone road and sidewalks, but it was a fun and memorable day. Annapolis is one of our favorite cities we’ve visited, and far exceeded our expectations.

The Best Things we Saw Today


The best thing I saw today was… “the Naval Academy, particularly the Chapel”.

The best thing I ate today was… “the crab cake at the delly”.


The best thing I saw today was… “the old buildings in Annapolis”.

The best thing I ate today was… “pumpkin chocolate chip ice cream”.


Tomorrow, we’ll explore more of the Havre de Grace area.

– Isaac and Faith

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