#Gates50States

Spring Break 2025 and we wanted to make it a drivable destination. Our original plan was to visit Virginia, Maryland, and Delaware, but the more we looked into Delaware, the more we found our interests lied in the north of the state, adding a lot more driving to an already full week. We decided to push off Delaware and combine it with New Jersey, and take more time, or at least less rushed time in Virginia and Maryland.

Our first glimpse of Maryland was driving through a brief portion of the western part of the state, Cumberland, on our way to Virginia in the dark of night, so we couldn’t appreciate much. It looked very pleasant, and like a place Jenn and I could spend a nice weekend for a short distance get-away. We were on a mission that night, however, so we pressed on.

For reasons we discussed on our Delaware post, we chose to add Delaware to this trip, and that led us through our second exposure in Maryland, Ocean City. I’m not sure there is a more quintessential beach town tourist trap. Henry enjoyed counting the various put-put locations with their massive dinosaur, mountain, and/or airplane statues. The volume of candy stores was quite the sight to behold, as well. Our drive was nearly unobstructed through town given we arrived in the morning, and before its boom season. No complaints from us. We’ll not be back.

Our visit to Maryland really began on our way from Delaware heading west on US-50 and crossing the bridges from the Delmarva Peninsula to Kent Island, then across the Chesapeake Bay to Annapolis.

Jenn found us a VRBO on Oyster Creak adjacent to the Chesapeake Bay, with a backyard facing the water. Springtime in Maryland makes for some chilly nights. It was perfect for a fire to roast hot dogs and marshmallows for dinner upon our arrival.

Nearly twenty years ago, in August of 2005,, Jenn and I visited this area for a long weekend. We stayed on Tilghman Island, rode our bikes to St. Michaels for an evening of big band music and crab dinner, toured the US Naval Academy, fished the bay, and first gained our appreciation for this area.

In many ways, not much has changed, and we liked it that way.

When we game planned for this visit with the kids, we knew we wanted to take in the Naval Academy, but also show them some history of the area, which led us to the Chesapeake Bay Maritime Museum in St. Michaels, learning about how oystering and other forms of boating on the Bay are endemic to life around here.

St. Michaels is such a cool and cute waterside town. They keep their shops and streets pristine, and the people are so friendly. Following the recommendation of our guides, we went to Limoncello for dinner and enjoyed pizza, pasta, fish, limoncello tiramisu, and chocolate mousse. Highly recommend!

Downtown Annapolis, though somewhat of a traffic nightmare, is quite walkable and very pleasant. For the first time, all three of the kids walked around with their own cameras. Henry took this of the capitol building.

Jenn and I were not an ounce less impressed with our stop at the US Naval Academy this time around. The Yard is beautiful, the very cool history is on full display, and our nation is in good hands with the leaders churned out at our military academies if what we saw here is a good representation. I was really hoping our tour guide would hold the kids’ attention and highlight for them things they could really hold onto. Mission accomplished.

We even got to speak with Superintendent Vice Adm. Yvette M. Davids toward the end of our tour. (The Navy’s calls the individual fulfilling the role of college president their Superintendent.) Right place at the right time!

On the recommendation of a client, and only a short walk from The Yard, we lunched at Chick and Ruth’s. They were jam packed when we arrived, but a table for five was just becoming available… we jumped on it. Photos of famous people and local politicians who’ve dined here line the walls, along with news stories relevant to the restaurant, and I’m quite certain they couldn’t fit another table into the place.

I figured, “When in Rome…” so I ordered the Jumbo Lump Crab Cake Wrap. Worth the price of admission. Jenn got the Crab Omelette, and she enjoyed that, too.