A Day in Annapolis, Maryland

View of the Capital Building from some of the quaint stores.

Annapolis, America’s Sailing Capital, is known for its rich Maritime history. Its name is almost synonymous with the famous Naval Academy on site. The Capital of Maryland, is laid between the Chesapeake Bay and Severn River. While the city still remains the State Capital of Maryland, you feel like you are going back to Colonial times especially when compared to hubs such as Baltimore and the District of Columbia, both of which are under an hour drive. The historic district, which includes the State Capital, Naval Academy and St. John’s College is less than a square mile and offers many quaint shops, restaurants and pubs. This makes for an easy day trip or a leisurely weekend destination. A friend and I did a PAWsitive weekend getaway with Buddy in Anna-pup-lis.

When to go: They have boat shows, both power and sail, in the Fall and Spring. Normally the second week in October and the first week in May. Based on your interests, either attend to see the mecca of preppy or avoid this weekend for the crowds. Similar to Washington DC at the end of March the Cherry Blossoms begin to bloom and offer a beautiful backdrop to the city.

Getting there: for those coming from Baltimore, there is a beautiful bike trail, the Baltimore-Annapolis which is part of the larger Greenway Bike path. From Washington DC you can take the metro and switch at New Carrollton Metro station.

Buddy, wearing his preppiest attire for Sailing season in Annapolis!

Style: While you are welcome to wear anything in any location. If anywhere was a place to bust out your favorite nantucket reds, seafoam blues, and Lily Pulitzer pinks. Please check out my friend’s pup, Buddy, all ready for his weekend away!

Buddy even had his own bed!

Accommodation: We stayed at The Graduate (126 West St), a hotel chain in most college towns. They have a charming nautical themed decor, and are even dog friendly!

Start your morning off with a coffee from Bitty and Beau’s coffee (124 Dock St, Annapolis, MD 21401), a delightful coffee shop run by employees with intellectual and developmental disabilities.

For those who are driving in the Pennsylvania Dutch Farmers Market (2472 Solomons Island Rd, Annapolis, MD 21401) is an Amish market with grreat fresh baked goods. 

Spend a few hours walking around the shops in Downtown Annapolis. Those interested should try to get a look at the State Capital. It is the oldest state capitol in continuous legislative use, and where the continental congress met from November 1783 to August 1784, during which George Washington resigned as commander-in-chief of the continental army.  If interested, take a tour of the U.S. Naval Academy. 

Outdoor seating and love music in the Market Space!

Due to COVID, tons of space downtown has been converted into pedestrian only walkways with lots of tents for outdoor seating (which means all the more places you can bring a dog!) There is live music playing all afternoon in the Market Space and many sailors in their bright whites to remind you that you are at home to the Naval Academy.

For those who enjoy some beach time, either head out to Sandy Point State Park or rent a kayak to enjoy the Chesapeake Bay. For those with a dog, Quiet Waters Park (600 Quiet Waters Park Rd), has a fenced dog park. It’s $5 to park but worth it to let your pup run free for a bit!

Great Frogs Winery (3218 Harness Creek Rd) which does first friday date night they have pizza, wine and music! They allow dogs but just ask that you call ahead so they can get to you appropriate seating.

Cheers to a leisurely, dog friendly weekend in Annapolis!

Published by Caroline

I am a full time school counselor in Brooklyn, NY and love to travel in the summer. My love of travelling started when I studied abroad in Barcelona in 2009, and then got my first job as an auxiliares de conversacion in Malaga, Spain for the 2011-2012 school year. Both povided me a homebase while travelling around Europe with friends. Now living in NYC, I take any opportunity to get out of town and see some place new. I want to inspire you to travel on any budget.

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