Curator’s statement
A weekend getaway in Annapolis, Maryland offers a delightful blend of quaint beauty, lively local culture and waterfront views. Nestled on the Chesapeake Bay, this charming town is perfect for a relaxing yet engaging escape.
Start your visit by exploring the cobblestone streets of the historic district, where colonial buildings (*1) and unique shops give you a glimpse into the past. You can stroll along the waterfront, where the scenic views of the harbor are breathtaking (I personally love the view during sunset) or take a leisurely boat tour to see Annapolis from the water.
History enthusiasts will appreciate a visit to the Maryland State House, one of the oldest state capitol buildings in continuous legislative use. The United States Naval Academy, where I had the pleasure of working in the past, is another must-see with its magnificent architecture and beautiful campus (also known as “the Yard”) overlooking the water.
For those who enjoy great food, Annapolis is a promising foodie haven. You can dine by the water at one of the many seafood restaurants, savoring local delicacies like crab cakes (or crab dips!) or oysters.
Outdoor enthusiasts can enjoy a variety of activities, such as biking along the water, kayaking and sailing. The city also offers beautiful parks like Quiet Waters Park, where you can enjoy art exhibitions and nature walks.
Overall, a weekend in Annapolis feels like stepping into a peaceful retreat with the perfect mix of history, modern charm, and nature. Whether you are there for relaxation or adventure, the city’s welcoming atmosphere will make it an unforgettable experience.
*1. Notable colonial buildings include:
1. Brice House
2. Maryland State House
3. St. Anne’s Church
4. The Hammond-Harwood House
5. William Paca House and Garden
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Things to do in Annapolis, MD
1. The U.S. Naval Academy (USNA)
Explore the iconic institution, where you can take guided tours of the campus (aka “the Yard”), visit the beautiful Chapel, where noticeable amount of midshipmen get married on their graduation day (Commissioning Day) every year and see the U.S. Naval Academy Museum, which showcases the history of the Navy and the Academy.
Be sure to check USNA website for USNA visitor requirements.
2. Maryland State House
As the oldest state capitol still in continuous legislative use, the Maryland State House offers fascinating insights into American history. Take a free tour to learn about its role in the nation’s early years.
3. Downtown Annapolis
Stroll down the cobblestone streets, where you will find art galleries, boutique shops, charming cafes and historic landmarks. It’s a perfect area for leisurely shopping and exploring the city’s past. You might just find your favorite gem. ;)
4. City Dock and the Waterfront
Annapolis City Dock is the heart of Annapolis’ harbor, lined with restaurants, shops and outdoor seating where you can enjoy views of boats sailing in and out of the harbor. It’s a great spot for people-watching and taking in the maritime atmosphere – which I used to do while waiting for my partner after work on some Friday evenings for date nights.
5. Boat tour or cruise
Discover Annapolis from the water by taking a boat tour or cruise around the Chesapeake Bay. You can enjoy scenic views of the city, its landmarks and the abundant wildlife in the bay.
6. Quiet Waters Park
This 340-acre park offers peaceful nature walks, art galleries and scenic views. It’s a perfect spot for bird watching, hiking or simply enjoying some quiet time away from the city bustle.
7. Hammond-Harwood House
An elegant historic home, the Hammond-Harwood House is a great place to learn about Annapolis’ colonial history. The house features beautiful architecture and art from the 18th century.
8. Fresh seafood
Annapolis is known for its seafood, especially its blue crabs. Visit one of the many waterfront restaurants to savor fresh crab cakes, oysters or other Chesapeake Bay delicacies. Popular spot include O’Brien’s Oyster Bar and Cantler’s Riverside Inn.
Places to eat & drink in Annapolis, MD
1. Bakers & Co.
Bakers & Co is cozy café and bakery known for its freshly made pastries, artisanal bread and delicious breakfast and lunch options. With a warm, inviting atmosphere, it’s a popular spot for enjoying coffee, sandwiches and homemade treats. The café offers a relaxed, friendly environment, making it a great place to grab a bite or catch up with friends. I’m usually not a fan of scones but I absolutely LOVED their scones – especially, their Apple and Ginger Scone was my favorite. My partner’s go-to was the Rhubarb and Strawberry Scone, he’s also very picky.
2. Naval Academy 1845 Coffee Gatehouse
Naval Academy 1845 Coffee Gatehouse is one of the three 1845 coffee shops they have at the U.S. Naval Academy (USNA), and this location was my favorite while I was employed there. It is a cozy coffee shop offering a variety of freshly brewed coffee, espresso drinks and pastries. It has a unique military-inspired theme, reflecting the spirit of the academy. The café provides a warm, inviting atmosphere perfect for grabbing a quick cup of coffee or relaxing with friends, family or even by yourself, while also offering merchandise and specialty blends to take home.
3. Pennsylvania Dutch Farmer’s Market
The Pennsylvania Dutch Farmer’s Market, locally known as the “Amish Market,” is a vibrant market offering a wide range of fresh produce, homemade baked goods, meats, cheeses and local specialties. With its welcoming atmosphere and friendly vendors, the market provides a taste of traditional Amish and Pennsylvania Dutch foods. It’s a great spot to shop for quality ingredients, unique treats and artisanal products in a cozy, down-to-earth setting. Their Breakfast Rolls and Pretzel Rolls were perfect for a quick bite, and my partner absolutely loved their pickles ("Miyagi" was his favorite after tasting almost 30 different flavors) – so many flavors to choose from!
4. Always Ice Cream
Always Ice Cream is a charming shop known for its delicious homemade ice cream and unique flavors. It’s a popular spot for both locals and visitors to enjoy a sweet treat. The shop offers a variety of creamy, hand-crafted ice creams, along with toppings and cones, making it a perfect place for dessert lovers to indulge in a fun, casual setting. My favorite flavors were Blue Angels (combination of blueberries and marshmallows) and Lemon Poppy Seed. :)
5. Federal House
Federal House is a lively restaurant and bar offering a mix of classic American dishes and seafood favorites. With its casual yet historic setting, the restaurant is a popular spot for both locals and visitors to enjoy a meal or drinks. Known for its friendly atmosphere, great service and waterfront views, Federal House serves up delicious meals like seafood platters, burgers and hearty entrees, making it a great place for a laid-back dining experience. Their Crab Dip, Cream of Crab Soup and Crab Cakes are my top picks.
6. Café Normandie
Café Normandie is a cozy French bistro offering classic French dishes like escargot (*1), coq au vin (*2), and duck confit (*3). With its charming atmosphere, warm décor and friendly service, it provides a relaxed yet elegant dining experience. The café is known for its delicious food, great wine selection and a welcoming vibe, making it a popular spot for both casual meals and special occasions. Request for a second floor table for those who’d like to enjoy the downtown Annapolis view.
*1. Escargot is a French dish made of cooked edible land snails, typically served in garlic butter with herbs.
*2. Coq au vin is a classic French dish made of chicken braised in red wine, typically with mushrooms, onions and bacon.
*3. Duck confit is a French dish where duck legs are slowly cooked in their own fat until tender and crispy on the outside.
7. Harold Black (Speakeasy)
Harold Black is a stylish and upscale cocktail bar known for its craft drinks and elegant atmosphere. A good way to get away from the hustle and bustle of modern night life and turn back time to slow down. With a focus on unique, expertly made cocktails and a sophisticated setting, it’s a popular spot for those looking to enjoy a refined night out. The bar offers a menu of creative drinks, along with a cozy, intimate vibe that makes it perfect for sipping cocktails with friends or enjoying a quiet evening in downtown Annapolis.
Need to know
While Annapolis is a lovely historic city, there are a few potential drawbacks:
1. Traffic and parking – During peak tourist seasons or events, traffic congestion can be an issue, and finding parking in downtown Annapolis can be challenging and expensive.
2. Limited public transportation – The public transportation options are limited, so owning or renting a vehicle is often necessary to get around, which can be a downside for those who prefer not to drive.
3. Tourist crowds – Annapolis is a popular tourist destination, which means it can get crowded, especially around historic sites, festivals and the U.S. Naval Academy, which may detract from the experience for those seeking a quieter environment.
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Nicole Todd
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