Exploring the Colonial Charms of Annapolis, Maryland

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Annapolis, sea-side capital of the state of Maryland, is a colonial American jewel box. Cobblestone streets lead from the Maryland State House, whose white dome peeks over centuries-old brownstones, down to the sailboat-filled harbor. The main thoroughfare is lined with quaint shops and restaurants; a few chains, yes, but mostly unique local establishments. Despite the mid-autumn chill in the air and precipitation that ranged from fine mist to light drizzle, it was still pleasant to walk around.

When Annapolis was founded in the mid-17th century, it was a royal colony of Great Britain. (Fun fact: Annapolis was named after Princess Anne, the first queen of the Kingdom of Great Britain. England and Scotland became unified during her rule.) Many of the well-preserved buildings bear plaques attesting to their age and in some respects it seems like not much has changed over the years. Take away the cars and you can almost hear the clop-clop of horses pulling carriages down the road.








Once a port-of-call in the slave trade, the quiet beauty of Annapolis Harbor belies its dark past. Today Annapolis is known as “America’s Sailing Capital” and is popular for its sailboat races. Even on non-race days, you’re almost guaranteed to see boats gliding along the horizon.




Annapolis is also home to the U.S. Naval Academy, an American institution that has been educating new classes of military officers since 1845. Visit during the fall, and you’ll find flags supporting the Navy football team flying all over town. If you like a man in uniform, this is the place for you!



During our visit, one street was bedecked with colorful chicken statues, part of an installation called “Hatching the Arts,” aimed at revitalizing the Annapolis arts district. I particularly enjoyed the little backpacker whose plaque read, “The world is my classroom.”



Dining options abound, especially on busy Main Street. The Red Red Wine Bar, as its name suggests, is an excellent place for a glass of vino. Interestingly, the bar keeps the wine on tap to simulate the experience of enjoying it straight from the barrel. The interior is warm and bright with funky decor and cozy plush seating from which you can enjoy a wine tasting and dishes made with Maryland crab. Actor Kevin Spacey has even visited this trendy spot!



Across the street, Piccola Roma serves up hearty Italian fare in a more intimate setting. We started with caprese salad with giant slices of fresh buffalo mozzarella and succulent bacon wrapped dates stuffed with goat cheese and drizzled with aged balsamic. Our entrees were even better: a creamy and tender seafood risotto and a crab ravioli in a delectable vodka sauce.


To fully appreciate the old world charm of Annapolis, I recommend having afternoon tea at Reynold’s Tavern. Built in 1737, it’s one of the oldest pubs in America and certain to transport you to another era. The dark wood floors and heavy furnishings exude 18th-century rusticity while white walls and gold-framed paintings keep the space from feeling drab. Tea was served on delicate and brightly painted china, with the snacks presented on a three-tier tray. Warm pies were a welcome addition to the traditional savory sandwiches and the hummingbird cake was a true sweet treat. But what really made this afternoon special was the selection of Jane Austen-inspired teas, in honor of the 200th anniversary of Pride & Prejudice. I chose the Mr. Darcy blend, which, like the character himself, took some getting used to but ultimately satisfied.







Red Red Wine Bar
Address: 189 Main St, Annapolis, Maryland
Pricing: Appetizers US$6-13; Wine flights average US$9-12
Piccola Roma
Address: 200 Main St, Annapolis, Maryland
Pricing: Dishes between US$7-23
Reynold's Tavern
Address: 7 Church Circle, Annapolis, Maryland
Pricing: Afternoon tea is US$18

What colonial-era American towns would you recommend visiting?

Heather Hall

Heather Hall

Passionate about travel, food, history and animals, Heather brings a curiosity and fun-loving attitude to most any experience that comes along. The Virginia native has lived abroad since 2011, and has visited more than 40 countries. Follow along as she explores the cultures and cuisines of the world on her blog, Ferreting Out the Fun!

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29 thoughts on “Exploring the Colonial Charms of Annapolis, Maryland

    • Thanks, Rosemarie! That street is right next to the state capitol building, so I’m guessing they are mostly businesses. But the side streets are all lined with private homes and guesthouses. It’s hard to believe that this quaint little place is just an hour from downtown DC!

  1. I love colonial architecture a lot. I remember enjoying finding some colonial houses in George Town in Malaysia, I loved how they contrasted with the local architecture. Another gorgeous example was Melaka always in Malaysia, have you been?

    • I haven’t been to Malaysia yet, but really want to go! I’ve seen photos of both of those towns and they look so charming. When we eventually make it back to Asia, that will be one of our first stops!

    • Thanks, James! It’s kind of hard to believe that someplace this quaint can exist so close to DC and the industrial wasteland of northern Virginia. I’ve been a few times and am always delighted. Looking forward to your post on Dalat!

  2. Thanks for all the great pictures. I love old towns. It’s been years since I
    visited Annapolis, Kay & Del used to live there. Glad you got to go visit.

  3. This is a really cool post and what an amazing tour you have taken us on of Annapolis. We almost went to Baltimore earlier this year with the plan of exploring Annapolis but we cancelled because of inclement weather. Hopefully we will get back there later this year and can see all this for ourselves.
    Chris Boothman recently posted…Dream Destinations – EgyptMy Profile

    • Thanks, Chris! That’s too bad you guys had to cancel your visit, but it probably wouldn’t have been fun exploring through all the snow we had. Try to visit in the fall if you can, it’s beautiful!

  4. I have to admit, I was definitely not expecting Annapolis to be so charming! Something about the name seems so dreary and drab to me (sorry, Princess Anne!)… Maybe I’ve just been watching too many episodes of The Wire so Maryland has taken on thuggish proportions in my mind. This looks like a wonderful place to enjoy a long weekend. Plus, crab + vodka sauce? That’s a recipe for success if ever there was one!
    Steph (@ 20 Years Hence) recently posted…Where & What to Eat in SavannakhetMy Profile

    • Haha, I never really thought about the name. Growing up in Virginia, I always knew that Annapolis was a little jewel box of a town. The rest of Maryland, not so much. Virginia has some exceptionally pretty colonial towns, like Fredricksburg and Williamsburg. If we were moving back to this area permanently and buying a car, I’d try to visit them all!

  5. Great shots! Cause of this post I really see the beauty of “Colonial Charms” ๐Ÿ™‚

    • Thanks Lauren! Annapolis is such a beautiful little place, and it’s less than an hour from DC, but if you’re not from around here it’s probably not on your radar. I just wish it were possible to get there without a car!

  6. Heather, it’s a very nice place. It seems like a peaceful and charming travel destination. I can just imagine how beautiful the streets look like in summer. Are you planning to get back there in the near future? By the way, the cakes look delicious!
    Agness recently posted…The Maldives In PhotosMy Profile

    • Agness, you’re right, it’s beautiful in the summer! I was there a few years ago for a friend’s wedding and it was perfection! Unfortunately I probably won’t get to go back to Annapolis for a while since we’ll be moving in a few months. But I’m sure I’ll have no trouble finding plenty of charming little towns in Europe! ๐Ÿ˜‰

    • That sounds like me when I visit my parents in Myrtle Beach. I end up spending half my time there with my mom at the outlet mall!

  7. I love the 6th picture where the tower or capitol is at the background hovering above all.. be the way are those residential homes on the left and commercial buildings on the right? i also noticed that most buildings are made of dark brown bricks .. and the street is also made up of brikcs or pavement, sorry what is that called? its not concrete nor asphalt road.. i love the entire color combination, the tree leaf tells its autumn?

    • Thanks to shows like the Wire, Maryland doesn’t have the best reputation. But Annapolis is definitely worth seeking out! Plus there are really cute historic inns and B&Bs which is think you guys would love ๐Ÿ™‚

    • Aren’t they great? I didn’t learn the story about them until I came home and did some research. Now I wish I’d located all of them!

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