Walkers, Ahoy! Ideas for Strolling in Annapolis
/Great eating, sightseeing and a stylish new hotel beckon visitors
The recently re-opened Graduate Hotel on West Street in Annapolis.
By Susan Able | Photography by Jennifer Chase | Sponsored by Visit Annapolis
There may be no better place to soak up the softer sun and breezes of mid-summer than on the Chesapeake Bay, with a walking tour of Annapolis on your list of must-do escapes.
Strolling, Playing and Staying: Let’s Take a Walk
In Annapolis, spending a summer day on a sightseeing walk is enchanting way to feel far away just a short drive from the DC area, and a hop-off well before possible back-ups on the Bay Bridge.
The beautiful Federal houses that line the town’s charming narrow streets reflect its Colonial past, but also fair warning that it means that it gets busy on weekends with regards to parking and navigating around by car. Also, some streets have been closed to provide more outdoor dining space.
So, advice from this local is to stow the car in a parking garage or lot and to put on those comfy sneakers for a good, relaxing walk. The steps will fly by as you enjoy the city’s nooks and architecture, Annapolis is reputed to have more 18th-century brick homes than any other city in the nation.
Consider making your walk a loop, and begin down on the waterfront at what is called Dock Square. The Market House and surrounding eateries have plenty of fuel to start your day. Local favorite Iron Rooster serves up chicken and waffles and City Dock is a coffee roaster and popular hangout.
Bitty and Beau’s on Dock Square.
But consider trying a new coffee shop on the scene this year: Bitty and Beau’s, which recently opened their fourth location on Dock Square. Founded in Wilmington, NC, Bitty and Beau’s is “coffee with a cause,” in the sense that it is run by people with intellectual and developmental disabilities. It’s a stylish, sweet place with lots of good swag for the shopping inclined. So, grab a coffee and head out, and around the corner, perhaps picking up a well-wrapped crepe from Sofi’s Creperie, doing carryout only.
The U.S. Naval Academy is your first ramble. If you’ve never visited, it is a worthwhile and inspiring stop. All you need to gain access is a Real ID (the new driver’s license) or a U.S. passport. The Visitor’s Center is closed right now, but you can still walk the grounds.
Make your way back up to Main Street, perhaps stopping for a carryout sandwiches at Mason’s Famous Lobster Rolls, where Maine lobster is served in all the classic formats. If you really love lobster, try the “Bar Harbor,” a roll that includes the meat from an entire lobster, even the tail. All sorts of interesting shops and eateries line the streets—including ice cream, of course.
The Flag House Inn B&B, Mason’s Famous Lobster Rolls and a sample breakfast item from Miss Shirley’s Café.
Venture forth to Church Circle and take a right to walk by both the Historic Church and the Maryland State House. Make a stop at the Maryland Federation of Art Gallery, which is currently open now. It showcases the work of local artists, almost all of which is for sale. Continue on to Maryland Street, one of our favorite streets in town lined on both sides with locally owned shops. Think antiques, books, gifts, gourmet foods and Galway Bay, an Irish pub that is now open with distanced seating.
There are several historic homes and small museums to visit, but if you are delighted by historic gardens you must make a visit to the William Paca House & Garden. The house tours are currently closed, but the garden is open. Operated by Historic Annapolis, the dreamy Colonial garden covers over two acres that has been painstakingly restored. Information and reservation information for a garden visit can be found here.
Meander back to Church Circle. If you continue north on West Street you’ll pass the Annapolis Visitors Center, which has re-opened from 9am-5pm daily. You’ll find friendly staff who have plenty of tourism info what is updated per Covid and lots of ideas. They can also connect you to great resources for sailing tours, walking tours and even tours by kayak. Luna Blu, another solid lunch option, is right next door. Across the street is Ram’s Head Tavern, with a storied reputation as a small venue for top music acts (which are postponed for now) but the Tavern is still open for dining and carryout, one of the best small venues for music around.
Cocktails? As you walk back down West Street, check out Dry 85, a bar with a terrific selection of their own selected barrel-aged bourbons. For $12, try a flight of three bourbons the owners have chosen directly from Kentucky bourbon country that are unique to Dry 85. The day we visited our flight included an Elijah Craig 8-year, a Maker’s Mark aged with French oak instead of American, and a 15-year-old Knob’s Creek, which showed its lovely age with a savory nuttiness. Want to learn more? The bar team is knowledgeable and happy to give you an introduction to the art of bourbon tasting. If bourbon and cocktails aren’t your thing, but wine is, you are in luck. The owners also own Red, Red Wine, a wine bar meant to be accessible, pretensions about wine be gone.
As you walk back to the starting point, foodies might want to pop into Spice & Tea Exchange to pick up shatteringly fresh spices and excellent spice mixes for all sorts of cooking projects. And Mills Fine Wine & Spirits has a great selection of locally distilled spirits and MD wines.
You’ve walked about two miles—you’ve earned whatever you will find to next to eat!
At the Graduate Hotel, above is a vignette from Camp Severn Shore, the hotel’s restaurant and bar. Below is a guest room.
Weekending
The arrival of The Graduate Hotel is a game-changer for accommodations in Annapolis. The stylish new hotel on West Street opened last fall and recently re-opened after closing due to the pandemic for several months. It is already a favorite will make you want to schedule your “adult runaway weekend”. Even if you aren’t planning on spending the night, you must walk through the hotel which has a nautical theme going in uniquely pleasing overdrive. Make sure to take a peek at the Atrium meeting room where over 500 pieces of nautical artwork line the walls, all collected from antique stores, auctions, and flea markets all over the country. It’s a visual feast of boating. Perhaps grab a cocktail at Camp Severn Shore, their on-site bar and restaurant and relax while enjoying the clever interior design.
To do a true Annapolis brunch, you have to try Miss Shirley’s Café, where they have raised the breakfast food bar high, including a Bloody Mary where the garnish could be considered a mini-meal. To encourage social distancing, use their Text Ahead Guest Waitlist, before arriving to the restaurant for dining to secure a spot. Dogs are welcome to join at the outdoor patio seating.
Feeling like a B&B vibe? Luckily there are plenty in town and one with a great breakfast experience and that “I could be a local” vibe: Check out The Flag House B&B near the Naval Academy which is open with COVID protocols in place, where your room comes with parking (a great plus!) and a to-die-for breakfast made with many locally sourced ingredients. We love wallpapers in The Commodore and The Far East Room.
At the U.S. Naval Academy in their summer whites, midshipmen stroll campus.
Crossing the Bridge: The Maritime Republic of Eastport
A second loop to walk involves crossing the main bridge in town, bookended on both sides by newly expanded Annapolis Yacht Club, to Eastport.
Eastport was once its own town; it was annexed into Annapolis in 1951 and has kept its own salty identity and its own flag. Annapolis’ Restaurant Row runs down Severn Street, and you can find fine dining for seafood at O’Leary’s or big aged steaks at the locally owned Lewnes Steak House, most all restaurants at this writing are offering dine-in following rules for social distancing. For casual food, try the rollicking Boatyard, with lots of Maryland specialties, oysters, crab cakes and daily specials that are all good and now with expanded outdoor dining. Favorites are the soft shell crab salad, the crab cake sandwich, the fried oysters and the huge Maine mussels. A hangout for recreational sailors and boaters, the bar is always humming. There is often a line, but it moves quickly.
Davis’ Pub is a favorite of locals. Dogs welcome at the outside seating, which has recently expanded.
If you want local color, try a place that is dear to the hearts of many: Davis’ Pub. It’s big claim to fame is that its crabby pretzel was featured by “Diners, Drive-Ins and Dives”’ Guy Fieri, but regulars also go for the burgers, gumbo and nightly specials. We love the deep-fried pickle spears, nicely crunchy and the perfect complement to almost any drink, including the local favorite, an Eastporter—vodka with a splash of cranberry. Outdoor dining is dog-friendly and the indoor dining is very people-friendly. Expanded areas are available to sit outside.
Want to stay on this side of the bridge? We recommend the Inn at Horn Point, a 15-minute walk from Dock Square and full of unique treats in a Victorian home. The rooms are all well-appointed and some have fireplaces. Like The Flag House, the Inn at Horn Point is well known for its wonderful breakfast, many ingredients coming from their own organic garden. The rooms are all different, and prices vary depending on the season and local happenings.
@susieqable is a writer. She is also Publisher and Editor in chief of Edible DC. A resident of Annapolis, she loves walking about the city and constantly finding new things to try on her explorations.
