Literary City Guide | ANNAPOLIS, MD

It’s what you do that makes your soul.
— Barbara Kingsolver, born in Annapolis, Maryland

Tour Guide: KARA FLYNN

Kara Flynn

A lifelong resident of the Annapolis area, Kara works as a communications director for a non-profit, freelances occasionally for magazines and newspapers, and enjoys cooking a wide variety of meals from around the globe for her two sons Ryan and Luke, and husband, John. (Photos by Kara Flynn.)



Relationship to Annapolis: Despite a few years here and there living in Europe, I have spent my entire life in the Annapolis area. No matter where I go, I always want to be back in this beautiful place. I married an Irishman from New York who I met working in Annapolis. I was very happy he wanted to settle down in the area where I grew up!

Writer you'd like to invite to dinner: Jane Austen. Perhaps she would share who the inspiration was for Mr. Darcy – that would be very interesting! 

Chef you'd like to prepare the meal: Yotam Ottolenghi, writer of my favorite cookbooks, featuring a wide array of vegetables and global ingredients.

Writing soundtrack: Kids arguing in the background and the constant sighs of a preening gray cat.

Pen or Pencil: Pen, although I am constantly losing them and stealing my kids writing instruments, or so they say!

Coffee or Tea: Both. In the mornings, I have a skim latte and in the evenings before bed, Earl Grey Tea.

Paperback or Hardback: Hardback. I’m old school. Even though I have books on my iPad, I still like to read a real book. 


Good Reads


Back Creek Books. A great little bookshop on Main Street. They have a nice selection of books that is easy to browse and not overwhelming in number.

The Annapolis Bookstore. With a charming location on Maryland Avenue, this bookstore has a homey feel. It actually feels like you are entering someone's personal home library. They have new, rare and used books and there is also a café which is perfect for lazy Saturday afternoons. 

Hard Bean Coffee and Booksellers. Coffee shop offering a nice atmosphere with free internet and a quaint bookstore located right next to the historic market house near Ego Alley.


The Sylvia Gaither Garrison Library. This library is located within the Banneker-Douglass Museum (BDM) on Franklin Street and supports the overall mission of the BDM by collecting and making available for use resources that document Maryland's African American Heritage.

The Nimitz Library. This U.S. Naval Academy (USNA) library is available to be used by USNA military and civilian staff and their family members, to personnel attached to the other activities of the Annapolis Area Naval Complex, and to local retired faculty members and retired military personnel. It is named in honor of Fleet Admiral Chester W. Nimitz, USN, who served as Commander-in-Chief, Pacific, during World War II.  

Annapolis Public Library. The main branch of our city’s library is located on West Street away from the center of town close to Homewood, a neighborhood with historic homes. There are a number of fun events for kids throughout the year and the library is a busy place for meetings and book sales. 


Annapolis Book Festival. A fabulous free community event held each spring at the Key School that features numerous prominent authors, a family-friendly comic-con for children and teens, and children’s activities.

St. John’s College Formal Lecture Series. Stop by one of the oldest colleges in the U.S. for poetry readings and discussions on literature each week during the school year.

Vice Adm. Ralph L. and Frances Shifley Lecture Series. Created to provide a platform for authors of military based non-fiction, this group hosts events five times each academic semester of the U.S. Naval Academy. 


Kunta Kinte Annual Arrival Ceremony. Every September 29th, a commemorative celebration is held at the Annapolis City Dock with the family members of Alex Haley, the author of Roots. This celebration acknowledges the arrival of Kunta Kinte to these shores as the beginning of his experiences in America.

Annapolis Tours by Watermark offers a War of 1812 Tour of Annapolis that will take you on many notable stops including where Francis Scott Key, the amateur poet and author of “The Star Spangled Banner” attended college at St. John’s.   

Middleton Tavern. For a taste of colonial Maryland’s history, head over to the Middleton Tavern, which was established in 1750. George Washington, Benjamin Franklin, and Thomas Jefferson are just a few of the notable patrons who passed through its doors. 

Schooner Woodwind. Annapolis is known as America’s sailing capital, and it’s lovely to take a sailing cruise during a summer evening and have a glass of wine while exploring the Chesapeake Bay. The Woodwind was the boat featured in the movie, “The Wedding Crashers,” which was captained in the film by Christopher Walken. 

Galway Bay. With 25% of Annapolis’ population rumored to be of Irish heritage (including my dear Irish passport holding husband), Galway Bay is a perfect replica to please the masses of a pub located on the West Coast of Ireland. It’s perfectly cozy on a cold and dreary day with authentic Irish dishes and lots of Guinness.  

Good Eats


City Dock Coffee. Excellent coffee with a variety of roasts to choose from in a lovely location on Maryland Avenue.

Ceremony Coffee Roasters. Locally roasted coffee with a hipster vibe in an out- of-the-way location, but worth the effort to find.  

Caffe Pronto. Delicious coffee and tea, super friendly staff and welcoming environment for getting some work done or catching up with a friend.

Bean Rush Café. This café is a perfect blend of local neighborhood coffee shop in a European style setting in West Annapolis.


Vin 909. The most delicious thin crust pizzas, especially the Spotted Pig, made with soprosetta and the maize, with speck and fresh silver queen corn can be found here. Wild boar meatballs and nicely priced glasses of wine. Do not skip the butterscotch pudding! 

Joss Sushi. Excellent fresh sushi and Japanese specialties in charming café setting on Main Street with an outdoor patio. 

Level Small Plates Lounge. A farm-to-table concept with drinks and a menu changing seasonally, which keeps things fresh and exciting along with a wonderful assortment of house specialty cocktails. The angels and demons cocktail is fabulously spicy!

Cantler’s Riverside Inn. Best place in Annapolis to indulge in Maryland’s famous crabs with a beautiful view of Mill Creek in an out-of-the-way location that is worth the trip. It’s fun to head down to the dock to take a look at the horseshoe crabs and other sea creatures kept in pools. 

Davis Pub. An awesome pub, popular with locals, with excellent crab cakes, sandwiches, great soups and more. Beer selection is quite good as well. The perfect pub to catch a sporting event and to make friends. 

Old Stein Inn. Anyone longing for a German biergarden needs to travel no further than a few miles away from Annapolis to enjoy Augustiner, Erdinger or Spaten beer with excellent, traditional German food. It’s even more enjoyable in the summer when patrons are encouraged to sing along to traditional German drinking songs.


Annapolis Ice Cream Company. Whimsical ice cream shop with homemade flavors including blue angel blueberry, lemon poppy seed and salted caramel. 

Bakers & Co. Small family owned bakery and café in Eastport with flakey croissants, morning buns and amazing cookies. 

Reynold’s Tavern. Reasonably priced traditional English tea time with delicious scones and clotted cream, miniature sandwiches and Victoria sponge cake held in a historic tea room from the 18th century. 

Literary City Guide | Annapolis

KARA's 5 Favorites

1. Favorite view: The Maryland World War II Memorial’s view over the Severn River, including the expanse of the U.S. Naval Academy and the historic Maryland State House. As a close runner up, the bluffs in a local private community, Bay Ridge, are absolutely stunning with views of the Chesapeake Bay Bridge and Kent Island in the distance. 

2. Favorite place to write: The butcher block table in our kitchen with a view of the pond behind our house and the many birds that love to bathe in the stream that runs into it. There are also occasional sightings of fox, deer and rabbits that are ideal for breaks. 

3. Favorite museum: The U.S. Naval Academy Museum features artifacts and is home to the Gallery of Ships. It is the last resting place of U.S. Naval hero John Paul Jones who uttered “I have not yet begun to fight.”

4. Favorite coffee shop: City Dock Coffee on Maryland Avenue. It’s very cozy and charming, particularly on a winter’s day. They also make a delicious Jamaican iced tea that is spiced to perfection!

5. Favorite thing about your town: Not only is Annapolis one of the most scenic towns in the Mid-Atlantic region, with a wide variety of museums and historic sites, but it also has a real small town flavor and charm that is not readily found anywhere else. I always joke that I can’t go anywhere without bumping into someone I went to elementary school with, but that’s the appeal. No one really wants to leave.