Exploring Annapolis at Sailboat Show Time

In Annapolis, “X” Marks the Spot for Visiting Sailors (and Pirates)

There’s a treasure trove of dining and shopping experiences less than 1000 paces from Annapolis City Dock. You’ve shivered your timbers with a day or two of Annapolis Sailboat Show booty, and now it’s time to walk the plank and search for grog, gold doubloons, and victuals. What? Your feet are too tired. No excuses, matey, because there are a boatload of restaurants, bars, gift and specialty shops, ice cream shops, coffee bars, and even educational opportunities mere paces from City Dock.

alex haley memorial city dock annapolis
Alex Haley Memorial statue at City Dock Annapolis. 

We’ve made it easy for you. Starting at the Alex Haley Memorial across the street from the Annapolis Market House, here’s a treasure map measured out in paces that is sure to satisfy all your cravings as you explore the more than 100 dining and shopping treasures less than 1000 steps from the City Dock.

Just as we were unfolding our map, Annapolis’s two-term mayor Gavin Buckley wandered by and gave us his two cents worth on how great a city Annapolis is. Unabashedly proud, the mayor, an Australian sailor who “washed ashore 30 years ago with $300 in his pocket,” is effusive in his praise of his adopted city.

“I believe this is the closest thing to a European city we have in America,” he says. “It’s an amazing, walkable, beautiful waterfront city with exciting history. I say with pride that we are becoming more of a foodie town, a shopping town, and obviously a great waterfront town. We have one of the most amazing vistas looking down from the top of Main Street; you can’t replicate it. We have the real deal—scale, fabric, 300-year history—I hope you have fun on your treasure hunt. It’s all here for the taking.”

oyster shooter middleton annapolis
Oyster shooters at Middleton Tavern. Pirate mask optional. Photo by Colleen Ligibel

50-250 Paces…

First stop on our quick tour of Annapolis should be the relatively new Museum of Historic Annapolis at the base of Main Street. It is within sight of the dock and costs only $5 for adults and is free for children. Though small, it gives a great overview of Annapolis history from the town’s first settlement until now.

While still in the dock area, it is worthwhile to take in the Alex Haley Memorial sculpture (some of which is enmeshed with the boat show’s fences, so come back at a quieter time when you can explore it without much foot traffic). The sculpture and plaques along the wall are a tribute to Haley’s book “Roots” and his family’s history. It reminds people of Annapolis’s significant connection to the slave trade of the 18th century. If someone wants to learn more about the history of slavery in the area, they can visit the Banneker-Douglass Museum on Franklin Street, a short walk up the hill (free entry). Also, in the general area of the dock (Pinckney Street) sits the old Waterfront Warehouse, which now holds a model of the layout of Annapolis in colonial days. 

Start your gastronomic treasure hunting at the revamped Annapolis Market House just across the street from the Haley monument. Here, you’ll find a great spot for morning coffee plus an eatery with local flair (raw bar, cocktails) to get your nautical taste buds blooming.

Turn right out of the Market House to explore the shops and dining venues along Dock Street. Pip’s Dock Street Dogs features more than 15 types of grilled sausages and hot dogs including the Almost Chicago Dog and the number one seller, the Coney Island Dog, a simple affair slathered with mustard, chili, cheese, fried onions, and jalapenos for $5.95. (Our dog was served by Pip, Ryan Lamy’s daughter, in whose honor the eatery was named.)

Head back towards Main Street to explore the multitude of restaurants that encircle the Market House. Be sure to have an oyster shooter at the city’s oldest watering hole (since 1750), Middleton Tavern. Legend has it that the likes of George Washington, Thomas Jefferson, and Ben Franklin supped at the establishment in the early days of Annapolis’s colonial past.

The Tavern was frequented by members of the Continental Congress meeting in the State House on such historic occasions as the resignation of General Washington’s commission, December 23, 1783; the ratification of the Treaty of Paris ending the Revolutionary War in January 1784;  and the Annapolis Convention which laid the groundwork for the Federal Constitution Convention held the following year in Philadelphia.

The Middleton Oyster shooter is a diabolical concoction that consists of a good-sized Bay oyster swimming in a mixture of a hearty cocktail sauce with a shot of vodka added for good measure. It is served with a shot glass of beer to wash it all down. Bottom’s up. My wife calls it an acquired taste.

Also in the “Market Space” a variety of bars and restaurants, including McGarvey’s Saloon, Federal House, and the Iron Rooster, offer indoor and outdoor seating (dog friendly) and live music. Right around the corner, the brand-new GOAT Annapolis at Randall and Prince George Streets serves delicious food with a Mexican flair and interesting cocktails. Enjoy the cozy atmosphere and tiny, charming patio out back.

acqua al 2 annapolis main street
Acqua Al 2 at the top of Main Street. The cocktail bar Harold Black is downstairs.

Eat and Drink Like a Local

SpinSheet staffers, most of whom live in Annapolis, recommend these bars and restaurants for meals, snacks, or cocktails:

Tostadas and cocktails at The GOAT on Randall Street

Tacos and margaritas at Vida Taco Bar on Main Street

Sushi at Joss Café and Sushi Bar on Main Street

Farmer’s Market Bowl and spiced shrimp at the Annapolis Market House

Cocktails and small plates at the Parley Room on State Circle

Crabcakes and fish sandwich at the Boatyard Bar & Grill in Eastport

Crab pretzel and gumbo at Davis’ Pub in Eastport

BBK breakfast sandwich and daily specials at Bread and Butter Kitchen in Eastport

Greek pizza at the Leeward Market in Eastport

The burger, sandwiches, and specials at the Eastport Kitchen

Locally brewed beer and fish dip at Forward Brewing in Eastport

parley room
The Parley Room on State Circle has indoor and outdoor seating as well as interesting cocktails and small plates.

250-500 paces

Now it’s time to head up Main Street, a half-mile collection of everything you would want to find in a dynamic waterfront town. As you stroll up Main Street and explore some of the more noteworthy side streets, be aware that your route up towards State Circle is fraught with danger… of the shopping variety. Be sure your credit cards are charged up and your shopping list is well in hand. Here you’ll find an amazing assortment of novelty, clothing, and casual dining spots that are guaranteed to catch your fancy.

Right at the corner of Main Street, stop at Buddy’s Crabs and Ribs for a taste of Maryland Seafood. If it crawls, swims, or floats on the Bay, Buddy’s has it on their extensive menu. Pull up a chair, put on a bib, and prepare for a seafood feast for the whole family (it’s kid-friendly). Oh yes, Buddy’s also does a great job with ribs!

Right up the street you will find Kilwins Chocolate and Ice Creamery, where each and every offering from ice cream delights to specialty donuts are packed with more calories than you can shake a peg leg at! The shop also sells fudge, caramel apples, and pastries.

pirate and mayor buckley annapolis
The author aka Capt. Cappy and Annapolis Mayor Gavin Buckley

750 paces…

While you’re strolling, don’t forget to stop into Chick and Ruth’s Delly, the quirky, old-fashioned diner with an attitude that offers up gigantic helpings of food and fun, complete with an all-hands-on-deck reciting of the “Pledge of Allegiance” every weekday around 8:30 a.m. The restaurant is famous for its gigantic portions, several of which are big enough to feed your whole crew. How about a six-pound milkshake or a three-pound corned beef sandwich?

Team SpinSheet’s favorite ice cream shop is across the street and up a block: the Red Bean, where they serve ice cream blended with your topping of choice from Heath bars to espresso beans. Homemade ice cream at Annapolis Ice Cream Company is yummy, too.

harry browne annapolis
The outdoor seating at Harry Browne's is first-come, first-serve. Next door is an awesome kitchen shop called Welcome Home.

Noteworthy spots…

Overlooking City Dock and Ego Ally is the upscale Choptank Restaurant, featuring an eclectic menu of local favorites and a killer view from the top deck. Be sure to bring your treasure chest. Like most things bright and shiny, The Choptank’s prices are not for the faint of heart. We like the chicken wings, crab dip, and calamari: apps that are a little easier on the wallet.

Another upscale restaurant, Acqua Al 2, located at the top end of Main Street in an old bank building, features a broad selection of Italian pastas and steaks. Expensive but worth every penny. If you just want a cocktail and a snack, check out the hip speak-easy-style cocktail bar downstairs called Harold Black.

Three destinations that are favorites of Mayor Buckley: The United States Naval Academy, “A world class institution” (open to visitors with a photo ID); St. John’s College, “Third oldest college in the US;” and the walk across the Eastport Bridge.

Walk across the Eastport Bridge at 6:20 at boat show time to see the best sunset in Annapolis, Maryland, on Spa Creek.

Our treasure hunt from the City Dock up Annapolis’s Main Street took us about 2000 paces to complete round trip. At every step a new adventure beckoned. From high end shopping, souvenir and novelty stores, impressive local history destinations, ice cold beer, buttery oysters, succulent crabs, gallons of ice cream, and pounds of mouth-watering fudge, the 2000 paces described herein will transport you to a pirate’s treasure chest of fun, education, and excitement.

Stroll the Avenue and Circle

Locals love Maryland Avenue, where you can capture one of the best photos of the Maryland State House and experience a quieter atmosphere than City Dock, which is only a seven-minute walk away. Among Team SpinSheet’s favorites are Galway Bay Irish Restaurant and Pub (corned beef), Annabeth’s of Annapolis (to-go wines and craft beers, snacks, and fun gifts), and the Old Fox Bookstore and Coffeehouse (don’t miss the garden patio out back for quiet coffee spot).

The outdoor tables at Harry Browne’s (on State Circle) are first-come, first-serve, so snag one if you can and enjoy the delicious food and view. Art lovers will appreciate the Circle Gallery, home of the Maryland Federation of Art, and its latest exhibit. While you’re there, take a walk through the Maryland State House, Maryland’s capitol (must have photo ID).

~by Craig Ligibel, with tips from Team SpinSheet