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Visiting Annapolis, Maryland


Annapolis, Maryland

This weekend, Connor and I were in dire need of a little getaway! Connor has been hard at work in med school (and I am so so proud of how well he is doing, by the way!) and I’m constantly thinking about the upcoming move. It was definitely time for a date day!

We’ve done the downtown DC thing way too many times to count, and weren’t really feeling like heading that direction with all the political unrest going on right now. So, we headed the other direction, towards the coast, to Annapolis, MD (which, as many tend to forget, is the capital of Maryland). Annapolis is gorgeous! It is so cute and quaint and I adore the fact that it’s near the water.

I’ll forgive it for being the home of the United States Naval Academy 😉 (Go Army!). After all, my husband did go to West Point, so we have a long-standing, friendly rivalry with the Naval Academy, and it can be weird walking around with Midshipmen all over the place. But we try not to show our true colors, and everyone is very friendly in the end!

Even though downtown Annapolis is relatively small, there is so much to do there in just one day. We’ve been there a few times before, and there are some places we keep going back to. Here’s a look at some of our favorite places to visit when spending a day in Maryland’s capital!




Quiet Waters Park

About 15 minutes from downtown Annapolis, Quiet Waters park is perfect for running, biking, taking your puppy for a walk, and just sitting and gazing and the Chesapeake. The park itself is actually quite large, and is a perfect getaway whilst being near a city. Oh, and it was also a perfect opportunity for me to test out my new camera!

My handsome husband acted as my model as I played with my camera. Fortunately, we mostly had the entire beach to ourselves due to the chilly weather. But I can only imagine how many runners, bikers, and puppies fill the park when the weather is nice! Also as a quick disclaimer, you do have to pay to enter the park. The daily entrance fee is $6.00. But, if you are a member of the military (like we are) you can enter for free!



Downtown Annapolis

Every time we head to Annapolis, we end up spending most of our day walking around downtown. I mean, how can you not?? It’s so cute and I honestly feel like I’ve gone back in time to a simpler era.


Annapolis is full of a history, which makes wandering the streets so much fun. The most obvious landmark in the town is the Maryland State House. It’s the white and grey steeple that you can see in a few of the pictures above. The state house served as the location of the United States Capitol from 1783 – 1784. This is also the location where the Treaty of Paris was signed, ending the Revolutionary War. I love how much history there is on the east coast! Of course, everyone knows about the history in Washington DC, which is only about an hour south of Annapolis. But, I’m afraid Maryland’s state capital is often overshadowed.

It’s also fun to walk by the Governor’s house, located right behind the State House. It’s a beautiful property!

Finally, another obvious landmark located near the State House is St. Anne’s Parish. The Episcopal church was founded in 1692. It’s definitely worth stopping by to gaze and the steeple up-close, or even take a peek inside at the beautiful stained glass.


We always stop in at our favorite wine shop, Mills Fine Wine and Spirits, to pick out a bottle or two of special wine. Connor caries the bottle of wine around with us – while simultaneously dragging me away from every clothing store we pass. It’s always fun to window shop, but there is always something, somewhere that calls my name. It’s usually a sundress 😉


Oh, and we must always stop for food! Now, Annapolis is home to a pretty well-known restaurant called Chick & Ruth’s Delly. Y’all, there is a reason this place is so popular! It is sooo goood!! You’re definitely missing out if you don’t get the crab cake and/or the chicken and waffles. And definitely splurge on a milkshake! You might want to make a reservation though, because Chick & Ruth’s is almost also packed, especially on the weekends.

If you head down to Annapolis anytime soon, please let me know! I’d love to hear about your trip! 


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  • Coryn
    February 8, 2017

    Next time you’re up there you’ll have to check out The Iron Rooster. That is my FAV restaurant up there. The food is super delicious! Also, the free Banneker-Douglass Museum is a perfect stop if you have 45 minutes or so to spare.

    • Jennifer Leigh
      February 17, 2017

      Thanks for the recommendation, Coryn! I looked up the Iron Rooster online and it looks delicious!

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