Annapolis & Dover

Driving from Annapolis, MD to New Castle, DE | Maryland and Delaware State Capitols | First State Historic Park, DE | September 2025

We rose early after our night of stealth camping in Annapolis, and drove right downtown to get started on our day. We began our morning walk by parking near the capitol building and walking around, checking out the different monuments and plaques in the area. Being Labor Day morning, it was pretty quiet, so we continued our walk to go see what we could of the Naval Academy, then grabbed some breakfast before getting back on the road.

Today was the last day of our drive to Wilmington, DE, and we only had an hour and a half of driving to make it to our hotel. So naturally, we turned that into a 4 hour drive by making a big loop around the Maryland counties on the East shore of the Chesapeake Bay. Unfortunately the national historic site along the way was closed for today, so we ended up just driving until we made it to Delaware. This drive would set us up for an easy finish of Maryland’s counties later on.

But first, we would be finishing Delaware by entering our third and final county in the state! With only 3 counties, it’s the easiest state to finish, as long as you have a reason to visit — which is why it took us this long, we just didn’t have a reason to come to this corner of the country. Our first visit was in April of 2023, when we were staying in King of Prussia and went on a little day trip to enter the state, making it our 50th state visited together, and Curtis’ 50th (I had visited as a kid — on 9/11 as a matter of fact — but that’s a story for another day). We entered New Castle county that day, “summited” the highest point, and went on a hiking and kayaking adventure in Brandywine Creek State Park. This spring was our second visit, where we entered Sussex county via ferry from New Jersey, and visited Bethany Beach in order to see the Whispering Giant statue. And now finally today, we entered into Kent county, thus completing our goal. And now thanks to Curtis’ fall assignment, we would be spending a lot more time in Wilmington and getting to know the state a lot better!

Since we still had plenty of time left, we drove to Dover and stopped to see the state capitol building. After walking around the building, I recalled that there was a historic site nearby (I’ve had it starred on my map for years at this point and I don’t remember why). We saw that it contained the old state house, so we wandered over to see what we could. Being a holiday, we weren’t sure if there was anything we could do, but the state house appeared to be open so we peeked inside. We found a docent there that was more than happy to tell us about this place, and so we spent the next hour learning about Delaware’s history and checking out the building.

Delaware may be small, but they are excited about their history! It’s always enjoyable to meet rangers and historians and the like who are passionate and knowledgeable about their area of study. We learned about the old state house and the early state history from the Revolutionary War through the ratification of the Constitution (Delaware is the first state after all). I think the biggest thing we learned was that when Delaware declared independent from Great Britain, they also declared independence from Pennsylvania (though they had been semi-autonomous for a period).

Once we were finished here, we finished up our drive to Wilmington, where we picked up a rental car and checked in to our hotel. Thankfully Curtis’ hours would be pretty light this week so we could spend some time enjoying the area!

Delaware with Charlotte, April of 2023