Travel with a Local: Annapolis, Maryland

Why should we visit your town/city?

The colorful town of Annapolis weaves historical significance with the vivacity of the waterfront and the peace of a small town. Though Annapolis now holds the title of capital city of Maryland, the town has also held the honor of United States capital. Annapolis acted as an epicenter for political action during the Revolutionary War and, as such, functioned as a temporary capital from 1783 to 1784, while the country was still forming.

Present-day Annapolis retains many colonial style-buildings along its red brick streets. The town invites its visitors not only to enjoy the historic air of the city but also to step back in time to experience some of the central events of the United States’ formation, including George Washington’s famous resignation of his commission as commander of the Continental Army, which took place in Annapolis’ Maryland State House. Restaurants and inns around the area likewise feature stories of famed guests from America’s beginnings.

From its perch on the Severn River, which feeds into the Chesapeake Bay, Annapolis serves as a hub for boating, sailing, fishing, and swimming, especially in the summer and fall months. But as any visitor to Annapolis soon will realize, the waterside, flower-lined streets create an enjoyable walkway in any weather, and the shops and restaurants that line Annapolis’ streets promise enchanting local goods throughout the year—from bay-inspired jewelry to freshly-caught fish and crabs.

Where should we stay?

Annapolis offers a variety of historic inns and bed and breakfasts. One notable inn is the Laurel Grove Inn: A few minutes’ drive from downtown, the quiet cedar-and-stone house sits on the South River, one of the rivers that connects to the Chesapeake Bay. For a more urban experience, drive downtown to Westgate Circle to find the Westin, a Marriott hotel with city-facing views and a luxurious bar and restaurant.

Where should we eat?

A few steps from the Maryland State House sits Reynolds Tavern, a quaint brick building—home to a restaurant, pub, and inn—that has stood in Annapolis since her colonial days. The restaurant’s classic decor and colonial-inspired afternoon tea service bear witness to its longstanding position in the city. Though the tavern’s lunch and dinner are both excellent—as is the backyard garden where customers may frequent the “1747 Pub”—the afternoon tea service undoubtedly outshines the rest of the tavern’s features, with fresh, buttery scones and a long list of various teas from colonial America and around the world.

Cross one of Annapolis’ many little bridges to the neighborhood of Eastport, and there you will find O’Learys Seafood. This humble-looking turquoise building near the water serves an array of finely-cooked seafood, from swordfish to tuna to classic Chesapeake Bay crab. Its interior displays blue-hued paintings and decor that, like the restaurant’s exterior, accord well with its thorough focus on the sea.

Downtown, any hungry ambler can find a handful of unique Annapolis haunts serving local fare and a local experience for only a few dollars. Neighboring the Naval Academy is Sofi’s Crepes, a fast-food alternative offering savory and sweet crepes wrapped in foil. Pick up a Thanksgiving crepe or Crepe Florentine and walk along the docks. Or take a few minutes’ walk up Main Street to the orange storefront of Chick and Ruth’s, a diner serving traditional diner fare, Southern food, and local classics—along with extra large milkshakes. Try one of their governor-inspired sandwiches, or try to split one of their famed milkshakes.

Which coffeehouses are the best and why (for coffee, for atmosphere, or for both)?

Bean Rush Cafe offers the best of both coffee and atmosphere. Its signature brews and seasonal drinks give a feeling of warmth similar to that of the shop itself. Their brewed coffee, whether light roast or dark roast, is my favorite of the cafe’s offerings, but they also make flavorful fruit smoothies and soothing lavender lattes. The baristas are kind, and many of the cafe’s customers mirror such kindness by starting conversations around the wooden tables.

Ceremony Coffee Roasters, while not as neighborly as Bean Rush, boasts—and roasts—some of the best coffee in the Chesapeake Bay region. Their baristas are especially proficient in pour-overs, French presses, and espresso. Ceremony has several locations, and while none are downtown, a Ceremony pour-over is worth the drive.

The Red Bean sits on Main Street and promises the best of all possible worlds: coffee and dessert. Not only does the Bean offer an array of traditional Italian coffee drinks, they also offer gelato and ice cream with mix-ins in the style of Cold Stone Creamery. Their cozy atmosphere is often filled with families, old couples, and local young people on coffee dates. The Red Bean’s creamy affogato proves their proficiency on both coffee and dessert fronts.

What sites should we see?

The Maryland State House, the oldest capitol in continuous use, features a free museum which allows its visitors to step into life in early America. Most notably, the museum invites its visitors to stand in and survey the room where George Washington resigned his commission at the end of the Revolutionary War. The State House overlooks the town from State Circle. The benches of its front garden, dotted with magnolia trees and filled with black-eyed Susans (our state flower), grant a perfect place to perch and watch the movement of the town.

Another beautiful historic spot to check out is the William Paca House and Garden, a Georgian mansion built in the 1760s by former governor of Maryland and signer of the Declaration of Independence, William Paca. The small admission fee is worthwhile: Stepping into the house is like stepping into the colonial period. The house’s lush gardens likewise invite visitors into the peace of a bygone era.

Downtown Annapolis is also home to the Naval Academy. Whether or not you have any connection to the military, you can walk onto the grounds of the Academy and wander its stone paths and manicured lawns down to the riverfront. The Academy truly is a grand sight to see, and you may catch a group of midshipmen marching and chanting a song.

Annapolis’ historic air and leisurely atmosphere create an oasis from the bustle of East Coast cities like Washington, D.C. and Baltimore. Whatever you decide to do in Annapolis—shop, walk, or sail—the town will delight you with its simple elegance and a refreshing bay breeze. 

Editor’s note: Travel with a Local gives the jet-setting (or road-tripping) woman inspiration for a quick weekend trip, or suggestions for when she’s just passing through a town for work. If you’d like to write about your town, review our Readers Write guidelines here.