Sunset in Annapolis. Photo by Bob Peterson.

3 Days In Naptown

Our Editors each share a day of surefire fun in Annapolis. 


Our editors each share a day of surefire fun in Annapolis.

Day 1

Getting there

 Dinghy Landing at Market St. Dinghy Landing at Market St.

This visit to Annapolis is all about using your dinghy—okay, a water taxi in a pinch—but really a dinghy would be ideal. I’ll explain why in a minute.

 Acton Park Acton Park

First, though, you have to settle somewhere. For the purposes of this expeditionary day, it doesn’t matter where or how. Here are your options: You can grab a mooring buoy on Spa Creek, off the Naval Academy, for example, or inside the bridge, or even on Back Creek between Jabins Yacht Yard and Port Annapolis. Or you can drop your anchor in Back Creek off of Eastport, near the little cove between Watergate and Mears would be ideal, but upstream past Jabins would be fine, or up Spa Creek in a little bay. Finally, you can opt for a slip, perhaps somewhere luxurious and resorty like Port Annapolis or Annapolis Landing. 

 Wild Country Seafood Wild Country Seafood

We can work with all of these options because, uniquely among cities, Annapolis has dinghy landings at virtually all the streets that end at the water. Cool, right? Okay, this is going to be fun!

Eating there

Time to rev up the engine, because our first job is to get something to eat, and
I know just the place. Steer your dinghy across the creek or around the corner to the bulkhead next to the Annapolis Maritime Museum. No, we’re not going to the museum, though it’s certainly a good place to throw in as long as you’re there anyway. We’re headed for Wild Country Seafood, which is tucked in—some would say hidden—behind the museum. It’s less than a block up Second Street from the dinghy landing. I don’t want to wear you out—that comes later. Wild Country is the splendid invention of Patrick and Patrick Mahoney, father and son watermen and the last of their kind in Eastport. They go out crabbing, oystering or whatever is called for by the season, and then they come back and open up Wild Country Seafood, selling fresh catch to go or cooking it up to take away or eat outside at a table under the trees. And, wow, is it good! You’re going to thank me for sending you there. 

Now that you’re full, let’s work it off. Back to the dinghy.

Being there

Now we’re going to do something I’ll bet neither you, nor your friends, nor even most of the people who live in Annapolis have ever done. We’re going to take a walk through the Annapolis nobody sees—the heart’s blood of this wonderful old city, the narrow, illogical old, haphazard streets of residential Annapolis. The part that is somewhere between a nightmare and impossible to drive through. Which is why no one who doesn’t live there ever sees it. So, grab a spouse or a couple of Labrador Retrievers and do this.

Take the dinghy up Spa Creek to either Shipwright or Market streets. Both have dinghy landings with a little floating dock. Watch your step at Shipwright—there are a couple of iffy boards on the dock. Presto, you are painlessly in the middle of one of Naptown’s original old neighborhoods. Climb out and walk around. I will point you in a direction, but it’s really up to you. If you land at Market Street, for example, you can walk up to Union Street, turn left, and then make a short jog left onto Conduit Street to Cathedral Street. Go right there, then left on Charles Street. At the end of Charles, you’ll be dizzy. Just kidding, at the end of Charles, you’ll find yourself at Acton Park, which is small and cozy and has a drinking fountain suitable for all sizes: adult, child and Labrador. It also has some goose sculptures, a couple of shaded benches and a very nice dinghy dock of its own. Well, yes, you could have just started here, but that misses the point. So hydrate, take a minute to rest and then find your own way back to the dinghy—maybe by way of a nice cold beer at Castlebay Irish Pub on Main Street or Galway Bay on Maryland Avenue. Heck, maybe both! 

 The  Sea Gypsy  The Sea Gypsy


Day 2

Pint-size Pirates


If you’ve spent any time around Annapolis Harbor you’ve no doubt seen the Sea Gypsy sail by, packed with giggling, arrrghing, pee-wee pirate wanna-bes shooting water cannons at a pirate in a red dinghy. It’s every bit as fun as it looks. 

 Little pirates attack Pirate Pete Little pirates attack Pirate Pete

When you and your little scalawags arrive at Pirate Adventures of the Chesapeake (311 3rd St. Eastport;, the upbeat crew takes the kids in hand and gets them all riled up for swashbuckling. The kids receive pirate names like Pacific Penny, Sneaky Sadie, Aye-Aye Audrey and Watch-Out Wyatt, then are decked out with painted-on tattoos, moustaches and pirate crew costumes. When all the little buccaneers are ready to board, the whole gang sneaks on tiptoes to the boat, whispering about hiding from pirates all the way.

On the ship, the little mates are led through an elaborate plot, complete with a hidden map, stolen treasure, a mishap with a mermaid, a close-call with the evil Pirate Pete, a water fight, a little bit of grog, and a bagful of booty to take home.

Parents and grandparents watch the melee from the shade of the bleachers in the stern, a perfect spot for taking pictures and standing by for hugs. My littlest (nearly four) needed a few after the near-boarding by Pirate Pete. My oldest (six) now believes whole-heartedly that there are mermaids in the Bay.

Of Foxes and Frites

 Fox’s Den Moules & Frites Fox’s Den Moules & Frites

Few things in this world will make you feel more hip than visiting what feels like a speakeasy hidden in plain site on a busy and vibrant Main Street. That said, you will feel like a total badass when you go to Fox’s Den on Main Street. Nestled between two boutique clothing shops (179B Main St.;, this gastropub is nothing short of clandestine. You can easily miss it. But you shouldn’t. 

After heading downstairs, you’ll certainly feel tucked away, but not in a dark-and-dreary way. This den is light and airy, with rustic charm that includes a brick pizza oven, a wall of reclaimed wood, and American Flags on the wall.

The menu is simple, with seven or eight appetizers and salads—dishes with beets, goat cheese and prosciutto-wrapped cantaloupe. Chefs Creations vary from entrées such as scallops with Israeli cous cous and crème fraiche, or duck confit chili mac, and shared plate items like the popular Moules & Frites—PEI mussels drowned in a garlicky white wine sauce and topped with duck-fat French fries and garlic aioli. Hot tip: Order this. Also order an artisanal pizza and dip the crispy-on-the-outside, chewy-on-the-inside crusts in the jus. It’s a mesmerizing combination. The pizza is great on its own, too, featuring a wide range of fun combinations including the Fig & Pig— fig preserves and shaved country ham, or the Boardwalk—shrimp, crabmeat and pesto.

Wash it all down with one (or more) of the bar’s wide selection of craft brews or creative cocktails like the Fox’s Sneaky Russian Neighbor (rhubarb shrub, vanilla & cinnamon infused breck vodka, soda), Corn N Oil (rum with pineapple and lime) or the For Fox Sake (bourbon, lemon, ginger and mint foam).

Because, Salted Caramel

 Annapolis Ice Cream Company Annapolis Ice Cream Company

There is no shortage of ice cream in downtown Annapolis. But there’s something seriously special about the Annapolis Ice Cream Company (196 Main St.; You’ll first notice it when you walk in and see thousands of decorated plastic spoons hanging on the wall and a waddle of welcoming stuffed penguins dotting the interior. But as you peruse the list of flavors you’ll really start to understand. There are 36 flavors in rotation. All made in-house. To rattle off a few: peanut butter Oreo, banana walnut, and salted caramel. Oh, salted caramel, you haunter of dreams, you. 

By the time you reach the counter you should be drooling. If not, you will be by the time you’re handed a cone. Be aware of portion sizes here, a single scoop cone holds more like three scoops. The only time this ever seems to be a bad thing is when you’re solo with several young’uns. Your clean-up-lick game must be on point. 

Day 3

The Rooster

 Iron Rooster Iron Rooster

Breakfast is waiting all day at the original Iron Rooster at 12 Market Space by the city dock. And what a breakfast it is, beginning with the first happy hour of the day from 

7 to 10 a.m. Monday through Friday featuring mimosas, a strawberry fizz and half-price house-made pop-tarts. The pop-tarts are famous. The next happy hour is 3 to 6 p.m. on the same days, offering the signature Raging Rooster, the Iron Crush and half-price apps. Orange juice and lemonade are freshly squeezed and the coffee cups are bottomless.

 The Fat Elvis Topping The Fat Elvis Topping

The Rooster’s definition of breakfast is like nothing you’ve ever seen including five benedicts incorporating fried green tomatoes, boursin cheese, roasted corn salsa, or marinated fried chicken with black pepper pan gravy or lump crab cake under a poached egg with Old Bay, or steak and cheese with caramelized onions. It gets crazier as you move to the omelet and waffle lists. The French toast is soaked in an apple/vanilla-bean batter and topped with maple/bourbon butter—mercy. For two bucks extra you can get a macerated mixed berry/ OJ compote topping on anything. Or just say to hell with it and shout for the Fat Elvis topping—bananas, peanut butter, bacon and chocolate sauce—then, go find a place to nap.

The burgers, soups and salads rally to the cause using grilled peaches, summer corn, waffle rolls, pickle chips, parmesan butter and you name it. Shrimp and grits are served with chipotle butter and pork roll. 

Having done the research, I have learned to flip to the sandwich page and point to the BLT&E—crisp bacon and egg served on a fried green tomato with garlic aioli, inside a sliced and toasted brioche. Get the egg over easy to help glue the thing together as you stuff it in, and keep your napkin handy.

At the end, you can choose to refuse the red velvet waffle with vanilla ice cream and chocolate sauce dessert. Or not.

Here’s a tip: Check in, follow or like the Rooster on social media and they’ll bring you a mason jar full of bacon for free. Clever. 

Don’t Give Up the Ship

 Naval Academy Museum Naval Academy Museum

Established in 1845 as the Naval School Lyceum to house historic models, art and equipment, the Naval Academy Museum has evolved to become the nation’s repository of naval war trophies, global survey material and diplomatic treasures. Preble Hall, a dedicated museum building, was built in 1939 and completely renovated in 2007 and ’08. The first deck presents our naval history from the revolution to today including the role Naval Academy graduates have played in times of war and peace. The second deck takes you through a breathtaking display of intricate ship models dating back to the Age of Sail. The ground floor contains a model shop where volunteer craftsmen work to preserve, maintain and enhance the collections. Read the full story in this month’s Talk of the Bay article by Jessica Ricks, page 30.

It’s free and worth the short stroll across the Yard from the Annapolis City Dock. We recommend parking in town and entering Gate 1 off of Prince George or Randall Street. Visitors over the age of 18 must show an ID at the gate. The museum is open Monday–Saturday, 9 a.m.–5 p.m. and 11 a.m.–5 p.m. on Sunday.

On Stage

 Bacon Brothers Bacon Brothers

The Rams Head Tavern phenomenon started in 1989 below street level as a cozy pub seating no more than 30. It made its mark by having a dependable selection of about 150 world brews and by selling custom-built sandwiches by the ounce. Dedicated beer drinkers can still gain fame and an engraved tab on the wall for achieving the full beer list over time. It’s a significant accomplishment. Since then, the venue has grown to become the definitive Annapolis brew-pub and restaurant occupying a sprawling space including on-site brewing, two bars, indoor and outdoor service, and a dedicated high-end performance venue along West Street at the top of the town. The main attraction is the stage, which stands out in the region as a major venue for road-tested acts. Memorable performances and recurring stars include John Hiatt, Ricky Skaggs, Leo Kotke, the Bacon Brothers, the Del McCoury Band, Spyra Gyra, Average White Band, Jerry Douglass, Southside Johnny, David Lindley, Darrell Scott, Robert Earl Keen, Buckwheat Zydeco,  the late Greg Allman, Richard Thompson. . . .

Take advantage of the venue’s Premium Experience, which costs no more but provides 10 percent off the pre-show meal, five bucks off parking in the Gott’s Court Garage (25 Calvert St.), a back-door escort to your table in the stage area and a complimentary mug of the home-brewed Fordham beer after the show. Just call and reserve your table well in advance. I’ll see you there for the next Darrell Scott show.

Where Sailors, Anglers and Their Kids Go

If you sail, fish, paddle, drink or all of the above, and you seek to find the heart of the Annapolis maritime culture, cross over Spa Creek into Eastport and take a seat at the Boatyard Bar & Grill. The food is excellent, drinks come in pint glasses, kids are welcome, the staff is all in for the team, and the walls are full of art and local treasure. It’s cool, and more than one percent of the tab goes to the Chesapeake Bay Foundation and other local conservation causes. You can’t and shouldn’t miss it, located on the corner of Severn Avenue and Fourth Street.