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Historic Annapolis, Maryland



“A small drinking town with a sailing problem.”

That’s the perfect phrase used to describe the quaint yet bustling town of Annapolis, the State capital of Maryland. Annapolis, which is located midway up the Chesapeake Bay on the Severn River, is also home to the United States Naval Academy and hosts Annapolis Boat Shows – a premier event management company that produces the world’s largest in-water boat shows.



This weekend, we took a trip down to this historic gem to check out the vessels, the eats, (and the Navy Officers, let’s be honest.)

Because we unknowingly decided to visit this magical town during one of the busiest weekends of the year, it was, at first, difficult to find parking. Luckily, we found some very affordable parking at the Annapolis Visitors Center right across the Severn River Bridge (we paid 5 dollars for 4 hours to park in the garage. SO much cheaper than what you find in the city!) Just a word of advice for those considering an Annapolis trip – the earlier the better! Not only will more parking spots be available, you will also have more time to experience all the wonderful shops and sights!

After parking, we took a very brief, 2 block walk to the Maryland State House Building. The symbolic building is the oldest state capitol still in continuous legislative use, and is the only state house ever to serve as the nation’s capitol.


Another cool rid-bit of info to know before your trip: During November 1783 to August 1784, The Continental Congress met in the Old Senate Chamber of this building. During this time period, George Washington came to Annapolis to resign as commander-in-chief of the Continental Army, where the Treaty of Paris was ratified, officially ending the Revolutionary War. How cool is that? (We are history nerds, sorry.)


After getting our history fix, we started our journey down Main Street, which is adorned with the same old brick sidewalks traveled by George Washington and Thomas Jefferson (we hope you know who these guys are.) An array of shops and taverns line the street that offer items such as jewelry, fine wine and spirits, seafood, boutique-style clothing, and handmade ice cream (which we will get to shortly!)


We passed shops such as Brown Eyed Girl (the cutest women’s clothing store), La Belle Cezanne (a diamond jeweler in which we only window shopped, sadly), the Annapolis Shirt Company (where we did indeed purchase the most adorable nautical tees!), and the Annapolis Black Dog General Store.


While all of these shops were enjoyable and unique in their own way, the way to our hearts is most definitely food! That being said, we stumbled upon the Annapolis Ice Cream Shop, a local creamery with shakes, sundaes, and housemade flavors with pies and cobblers mixed in (yes, you read us right: PIES mixed INTO the ice-cream).


Annapolis ice cream offers seasonal flavors such as pumpkin pie, cherry pie, pecan pie, gingerbread cookie, candy cane, and cinnamon. We went with a giant scoop of apple pie (which has an entire slice of pie in each giant scoop!) Chunks of crusty, sugary pie dough and soft, cinnamon encrusted apples were in every bite of vanilla bean ice cream. The friendly staff recommended we top it with creamy caramel (genious!) but we opted for the plain ice-cream so we could truly enjoy the uniqueness. Don’t worry, if traditional ice cream flavors are more your thing, they have plenty of those, too!


As we continued down Main Street (about .7 of a mile), we walked past the Annapolis Yacht Club that sits right before the Severn River draw bridge. We approached the bridge and were greeted with 360 degrees of breathtaking views! Hundreds of sailboats and yachts filled the harbor as the sun peaked out through the clouds. (In case you are wondering, the United States Power Boat Show runs October 15-18, but Annapolis Boat Shows also hosts a Spring Sailboat Show and a United States Sailboat Show.)


There was so much beauty in every frame, that we couldn’t pick just one photo to share with you (FYI – the picture below is of the Annapolis Public Water Taxi that transports you to numerous destinations around the harbor, and ranges from $3-$8 depending on length of travel)!



As the sun started to set, the wind began to blow in cold, gusty bursts (which was too cold for these born-and-raised southern girls)!

We started back up Main Street and stopped in Starbucks for a coffee to warm up before heading to the Annapolis Visitors Center. Another reason why we recommend using the visitor’s parking at the top of Main Street, is so you can enjoy the views both on the way down the street into the harbor, and on the way back up – both views are very different!


While summer is probably the best time to explore Annapolis and all it has to offer, taking a trip in early-mid fall is also encouraged, as the foliage change serves as a perfect backdrop to the deep red hues of brick and colorfully painted town homes that line the quiet streets.


Filled with history, fine cuisine, and fun, Annapolis offers activities and enough exploring for people at any age. What are you waiting for?

  1. Liz @ I Heart Vegetables says

    I’ve never been to Annapolis but my husband have a goal of seeing all the US Capitals so that’s on our list! It looks like a cute spot!

    1. Karen Hopkins says

      We really enjoyed it. Let us know if you ever make it there! 🙂

  2. Fatima says

    Including it in my travel list. Thanks for providing a lovely virtual tour. Great pictures! 🙂


    1. Karen Hopkins says

      Awww no problem! Thanks for the kind words! Let us know when you go 🙂

  3. Brenda Lee says

    I haven’t been to Annapolis in quite some time so i really appreciate your pictures! Thanks for sharing!

    1. Karen Hopkins says

      You’re welcome! Glad you liked them. Thanks for the support 🙂

  4. Rachel Martin says

    I’ve never been to Annapolis, but you snapped some GORGEOUS pictures! Glad you had so much fun!

    Xo, Rach

    1. Karen Hopkins says

      Thank you Rachel! I’m glad you enjoyed the photos. We hope you can make it there one day soon!

  5. Claire'scomfycorner says

    Looks like a great place to visit, your photos are amazing 🙂

  6. mandipimental says

    Gorgeous photos, and cinnamon encrusted apples sound like they need to go in EVERYTHING.

    1. Karen Hopkins says

      Thank you! We agree- the best apples for fall!

  7. Ursula @blueridgebeautyblogger says

    I feel that I have already visited this place although I have never traveled to Annapolis, MD, in person!! I got to remember that Ice cream shop!


  8. Brooke Fedigan says

    It’s so pretty. We enjoy Newport RI every year and keep saying we need to get down to Annapolis too. My husband has a good friend that lives there and of course they have a beautiful boat.

  9. Sarah says

    Awesome pictures you got there. The marina is so pretty. Would love to visit Annapolis someday. 🙂

    1. Karen Hopkins says

      Thank you!! If you ever get out there let us know how you like it 🙂 It’s gorgeous there! Thanks for the support.

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