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Pursuit of it All

Weekend Adventure in Annapolis, Maryland

2020 has been a year of incredible ups and downs. It’s a year where time has felt weirdly suspended. The days and weeks have melded together and concern for safety and restrictions have made it nearly impossible to unwind and relax.

I don’t know about you, but I’ve always been a bit of a workaholic. I really live for my time off. The pandemic, combined with my kid’s college schedules, made a big family vacation impossible this year.

So my husband and I decided to plan a local weekend getaway to at least celebrate our wedding anniversary. Annapolis is roughly one hour drive from my home in Frederick, Maryland and has been on our list of places to explore for some time now. What better excuse to get away from it all?

Where We Stayed

We really wanted to soak up the historical vibe so my husband and I chose to stay for a few days in an inn as opposed to one of the more mainstream properties. So we booked our stay at the Governor Calvert House, one of the Historic Inns of Annapolis.


The Governor Calvert House is located right on State Circle and dates back to 1695. Once owned by a prominent local family, Governor Benedict Leonard Calvert occupied the home while holding office. The property has been expanded four times during its transition from a private residence to apartments and finally, a hotel.

We chose to book a room with a balcony overlooking the State House and while we most certainly researched online before booking our stay, we were blown away by how charming and comfortable it turned out to be. It was a great blend of modern-day amenities and historical charm complete with a hypocaust room and resident ghost.

It was absolutely perfect.

Our balcony view was worth every penny.

Fun Fact: Apparently, many of Maryland’s state legislators stay at the Governor Calvert House each year when they convene at the Maryland State House. Can you even blame them?

What We Did

My husband and I are the perfect travel partners. Our time clocks are completely in-sync and we both adore actively exploring. There’s something about investigating on foot that gives you an insight into the city’s vibe, that magical combination of sights, sounds and smells that makes each area unique. For us it is the best way to immerse ourselves in the atmosphere and connect with an area’s history and culture.

Annapolis is incredibly walkable and hospitable. We wandered for hours with no agenda and always managed to end up somewhere charming. 

Fun Fact: Annapolis is consistently ranked as one of America’s most walkable towns. The waterfront town consists of 300-year-old buildings that house restaurants, pubs, art galleries and boutiques. Sightseeing for days!


Of course, a huge part of any enjoyable trip is food. And my experience in Annapolis did not disappoint. We literally ate our way through town, if I’m being honest.

A few personal recommendations include Chick & Ruth’s Delly for breakfast. Chick & Ruth’s has been an Annapolis institution for over 50 years. It’s quite diner-esque. (I’m pretty sure that’s not even a word but you get my drift.) I recommend the breakfast wraps. You’ll stay full for hours.

Honestly, we had a great experience at every establishment we visited. The Tecumseh Pizza at Harry Browne’s Restaurant (Mushrooms, truffles, fontina cheese, and fresh mozzarella) was INCREDIBLE. I regret not taking one home with me. I also highly recommend the coconut mule (trust me on this one) and French onion soup at Federal House Bar & Grill. And don’t you dare leave town without visiting Storm Bros. Ice Cream Factory. There are 40 flavors to choose from and every single one I sampled seemed to be as good as the last. Nearly impossible to pick one flavor to walk out with.

When it came time for a celebration dinner, we opted to dine at Carrol’s Creek Cafe which was recommended to us by a local. It turned out to be one of those special meals that was perfect in every way. We sat on the patio and literally watched the sunset and luxury boats float by.

It’s pretty rare that a meal (and service) lives up to the hype but this experience was truly memorable. I can’t recommend it highly enough! For those who might be interested, we ordered the Cream of Crab soup, Herb Encrusted Rockfish Fillet, Pan Seared Scallops and Apple Caramel Tarte. Perfection!

And what visit to Annapolis would be complete without a tour of some sort? There are tons to choose from but we opted for a ghost tour. (Yep, more walking!) It was fascinating to learn about the history of Annapolis with a good measure of spirit lore thrown in. 

During our tour, we visited ghostly haunts like St. Anne’s Church, the Maryland Inn, the Maryland State House and the James Brice House. (And also learned about the ghost supposedly lurking in the Governor Calvert House.)

I enjoyed the tour so much that I ended up buying a Haunted Annapolis book during our stay and talked my husband into visiting some of the other haunted spots on our own later in the weekend. 

Fun Fact: Annapolis was not only home to four of the original signers of the Declaration of Independence it was also a hub for pirates and privateers. In fact, Edward Teach, better known as “Blackbeard” was a frequent visitor to Annapolis. 

What We Discovered

One of the best things about exploring an area on foot is the serendipity of it all. For example, on our first morning in Annapolis, we went looking for a coffee shop. We casually asked someone on the street for the nearest locally-owned coffee shop and were directed to what would become our go-to favorite spot in the city.

Brown Mustache Coffee is located off of Maryland Avenue in the back of Old Fox Books (which was not open at the time we made our first visit because we are super early risers). In order to get to Brown Mustache, we had to walk between two buildings on a very narrow pathway to the back of the building where we found an outdoor patio to order coffee.

I was immediately enchanted.

In the back of this space is a lovely outdoor patio/garden area that is the stuff of dreams. That first morning we sipped coffee in a corner of the courtyard, ate delicious scones made of maple syrup and pecans and admired our surroundings.

Some of the surroundings included:

  • A suit of armor
  • Fairy lights
  • Directional signage leading you to Godrich’s Hollow, Atlantis, Paris and Oz 
  • An outdoor playhouse made of books

I was gloriously in my element and a little speechless. My husband was amused (as you can imagine) but enjoyed it just as much as I did. (We’re totally stealing the directional signage idea for our own backyard.)

Luckily for us we made the discovery of Old Fox Books and Brown Mustache Coffee early on in our trip. We visited a few more times that weekend browsing the store and having early morning conversations with the barista.

If you’re a bibliophile and have a heart for independent booksellers I highly recommend visiting Old Fox. Not only do they have a great selection of new and used books, they also have a delightful way of incorporating humor and pieces of the literary world in their decor. My personal favorites were the Harry Potter room found under the spiral staircase, a Gilderoy Lockhart autographed photo in the bathroom, and a matching quote over the archway from another one of my favorite independent bookstores, Shakespeare and Co (Paris).

Trip Safety

One might think that it would be risky to venture out for a weekend in Annapolis but I highly disagree. The city, and the people found within it, are very safe. I saw no evidence of masks not being used or safety precautions not being taken. In fact, I was quite impressed by the levels of precaution being displayed by local merchants and restaurants. Mechanisms for social distancing, hand sanitizing and mask wearing where fully in place.

My husband and I chose to do most of our exploring in the early morning which allowed us to wander the streets during a time many were still indoors. We also took extra precautions while shopping and eating. I always carry my own hand sanitizer with me, although every place we visited had sanitizer for use.

Honestly, the area really made it easy to feel comfortable. I’m guessing that is partly because the Governor’s house is smack in the middle of the historic area. Nobody messes with Larry these days. 😉

Prior to us leaving for the trip my parents had gifted us with a UVC/LED Handheld Sterilizer Wand. I used that light on every knob, switch or common surface in our room just to be extra cautious. You never know, right?


Our weekend visit to Annapolis, Maryland was a wonderful break from what has been a very challenging year. It gave us the opportunity to celebrate and take a much needed mental break.

We ended up falling in love with the area and vowing to visit again with friends in the spring!

Blogger. Marketer. Deadline juggler. Flibbertigibbet. A fan of all things glitter and girly, Jen’s passions include gabbing with girlfriends, running marathons, sipping (okay, gulping) cocktails and waxing poetic about the tortured soul of Professor Snape. Rarely found without her nose in a book (or her iPhone), she acknowledges that her level of geekery might not be for everyone. Consider yourself warned. Her ultimate goal in life is to be a professional wanderer of the internet or Amy Poehler’s BFF. (Both totally accomplishable, of course.)

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