The Pandemic have you down? Bored to tears but not willing to brave the hassles of bigger cities like Baltimore, Washington or Philadelphia? If you’re looking for a quick get away or change of pace you should check out Annapolis. A great city to visit on the Chesapeake Bay during “normal” times, also turns out to be a surprisingly good choice during the pandemic.
An historic colonial town founded in 1649, Annapolis is home to both the U.S. Naval Academy and St John’s University and is known as America’s sailing capital. Located where the Severn River meets the Chesapeake Bay, Annapolis offers a great opportunity for those who enjoy meandering old neighborhoods with pedestrian safe streets, historic sites, and a vibrant bar/restaurant scene. Though small enough to pop into for lunch and a quick look around, Annapolis is deserving of a more in depth stay. A good suggestion would be to spend two nights and three days getting to know one of America’s best kept secrets.
As with most of America, Annapolis has had to adjust to life with COVID 19. Restaurants and bars are at limited capacities, masking is now a way of life and social distancing is widely practiced. But Annapolis has also found ways to safely cope with the various restrictions that have been put in place. Heated outdoor seating is now a staple in Annapolis and has helped compensate for a decrease in indoor capacities. Most restaurants have ramped up their “take out” service allowing residents and visitors the choice of eating in the city’s various park like settings should they not be comfortable eating inside. Many streets once filled with parking spots are now filled with tents and tables providing a surprisingly festive atmosphere while allowing for social distancing. Most of the locals have welcomed the changes and hope they live on as the Pandemic fades into history. As an added bonus, the once curtailed operating hours have now been rescinded allowing the bars and restaurants to stay open well into the night.
From a visitors standpoint, Annapolis is best split into three distinct areas; An Uptown area, more simply referred to as “West Street”, Downtown, commonly referred to as DTA (Downtown Annapolis), and Eastport, proudly referred to by its residents as The Maritime Republic of Eastport, having claimed it’s “independence” from Annapolis after a temporary closure of the Spa Creek bridge years ago. Each has its own personality, and numerous eating and drinking establishments. Here’s a snapshot of each area with some recommendations on what to see and where to eat or enjoy a cold beer.
Downtown Annapolis: The largest area and deserving of the most time. It’s defined by Main Street and the City Dock and would also include, the State House, Naval Academy, St John’s University, and Maryland Avenue.
Start by meandering down Main Street towards the water from St Anne’s Episcopal Church. Main Street is lined with quaint shops, restaurants and bars, and provides an excellent view down to City Dock. Check out Chancery Alley to your left for a unique picture opportunity of the Maryland State House. If on Main Street in the morning, stop into Chic and Ruth’s Deli for a great breakfast and catch the Pledge of Allegiance which is recited every weekday morning at 8:30 AM (9:30 AM on the weekends). Pop into ACME Bar and Grill or O’Briens for lunch, a cold beer or to watch a game. For a nice break on a sunny afternoon, head to Pusser’s at the Waterfront Hotel on Compromise St and sit out on the deck bar watching boaters show off their expensive yachts on “Ego Alley”. For an excellent wood fired, brick oven pizza experience coupled with a good craft brew, visit The Fox’s Den, a basement bar that’s easy to miss. Look for the fox sign halfway down Main Street. You’ll also find Vida Taco Bar and Preserve, two excellent restaurants mid way down Main Street.
Heading left into the Dock Street area at the bottom of Main Street, take some time to walk through the City Market for counter Sandwiches and Seafood. The market also serves up craft brew which you can enjoy either inside the market or at one of the outside tables. Beyond the Market are two of Annapolis’ most iconic bars, McGarvey’s, and Middletowns, both local favorites known for excellent ambience, food and service. Continuing down Dock Street you’ll pass Dock Street Bar and Grill as well as Armadillos, both great place to grab a beer and a bite. Finish off your walk around the Dock with a rest on the benches looking out to the Bay. Off to the left you’ll see both the Chesapeake Bay Bridge spanning five miles over the bay to Kent Island as well as the historic Radio Towers used to communicate with Submarines during WWII.
Head back up Dock street and turn right at on Randall St at Middleton’s to head down to the visitors entrance of the U.S. Naval Academy. While touring the grounds (the Yard as the Midshipmen call it), make sure to stop in and see the Naval Academy Chapel and the Crypt of John Paul Jones which lies below. Other must sees include the Rotunda of Bancroft Hall, the statue of Tecumseh, and the Naval War Museum located in Preble Hall. The Naval War Museum in particular is a hidden gem which documents the Navy’s history from the Revolutionary War to present times. Head up to the Academic buildings, Chauvenet, and Michelson Halls. See the spot where Albert Michelson, the first U.S. scientist to be awarded the Noble Prize, conducted his “speed of light” measurements. If open, stop into Dahlgren Hall and grab a bite to eat and a beer.
From the corner of McGarvey’s, head up narrow Pinkney St to catch a glimpse of the colorful and unique row houses that make up some of the back streets of downtown Annapolis. A quick left on East Street will lead up to the Maryland Statehouse. Stop in and see the spot where George Washington resigned his commission. Once the temporary Capital of the United States, the Statehouse and its grounds are full of historic artifacts and statues. Continuing around State Circle, head down Maryland Avenue for additional shopping opportunities. If in the area for lunch or dinner, stop into another of the local favorites, Galway Bay, for excellent traditional Irish fare and another cold beer. Walk it off by heading down Prince George St to amble around the campus of St John’s University, founded as King Williams’ School in 1696.
Eastport: An historic part of Annapolis which was largely farm land until the late 1800’s. While at one point in its history it was known as the “blue collar” side of Annapolis, that’s no longer the case. Though it retains much of its Maritime charm, Eastport is now prime real estate and nearly every house has been beautifully renovated with many selling for a million dollars or more. It remains an interesting place and worthy of a morning or afternoon stroll and a visit to one of the many restaurants and bars. If visiting Annapolis in the warmer months, head over from the City dock by Water Taxi. The views back to Annapolis make it all the more memorable. You can also simply walk down Compromise St and cross Spa Creek on the Eastport Bridge while still taking in the tremendous views of the marina’s below.
The best way to experience Eastport is by walking. Once across the bridge, turn left down Severn Ave, known as Restaurant Row, past Carol’s Creek Restaurant, The Boatyard Bar and Grill, O’Leary’s Seafood, Lewnes and Ruths’ Chris Steakhouses, and the Chart House to 1st St. Head right on 1st St. and meander through the neighborhood. The water end of many of the streets will have benches and grassy areas to sit on with views out to the Bay or across to the Naval Academy. Stop in for a coffee at Leeward Market (located on the corner 2nd St. and Chester) and drink it by the water at the end of 2nd street. The end of 2nd St is also the site of the Maritime Museum which is free and an excellent place to learn the history of Eastport and the Chesapeake Bay. If you’re hungry, Wild Country Seafood, located behind the Maritime Museum on Bayshore Ave. is a hidden “whole in the wall” gem with picnic tables out front to eat on.
Down the street from Leeward Market on 4th and Chester is Davis’ Pub, a long time locals favorite who’s motto is “Where there are no strangers, only friends you haven’t met”. Stop in and chat up the locals while having a crab cake or a pulled pork sandwich and a cold beer, or grab some take out and eat it in the little park on the water right across the street. If Davis’ doesn’t suit you, head back up 4th to Severn Ave. and stop in to the Boatyard Bar and Grill. Don’t forget to stop into the recently opened Forward Brewing along the way for a unique brewery experience in Eastport.
Uptown/West Street: Years ago, the West Street bar scene only reached a couple of blocks off of Church Circle and Main St. These days it begins about a half a mile out West St. at the Taylor St traffic circle. If you’re in Annapolis for a couple of nights, make sure to spend one late afternoon/evening bar hopping the West Street area. And set some time aside to visit the Banneker-Douglass Museum (84 Franklin St), Marylands Official “Museum of African American Heritage” to see excellent exhibits on the areas rich African American history. And check out the vintage photos of Annapolis in the 1950’s adorning the parking lot walls outside of Stan and Joe’s.
Start by taking the free trolley out to Fado, an upscale Irish Restaurant and Bar. If you’re a little worn out on Irish fare from the many choices in the Downtown area, try Carpaccio, an Italian Restaurant co-located with Fado, that some consider to be the best Italian fare in Annapolis. Both places serve good food and drinks, and in the summer, both share the same outside dining space. Heading back downtown, next up on the same side of the road would be Sailor, a new Oyster Bar with a couple of heated outside tables along with some inside seating. Try some of the local oysters or choices from up and down the coast. Continue downtown by foot making sure to stop at Metropolitan just a few steps away for a drink on their rooftop bar. In pre-covid times, Metropolitan was one of the more popular Annapolis music venues. While meandering back toward Church Circle from Metropolitan, there are a couple of Hotel Bars to choose from, however a better choice might be to have a drink and some small plates at the trendy restaurant Level located on West Street a little closer to town.
Now within a block of Church Circle and Downtown Annapolis, your night is really just beginning. Tsunami, Stan and Joe’s, and Ramshead are all worthy of a stop. Tsunami serves food with an Asian flair (limited hours due to Covid), Stan and Joe’s is mainly “pub grub” and regarded as one of the better bars in Annapolis, while Ramshead is the place you want to go for some good Fordham micro brew and a slightly more upscale menu. Whenever you decide to call it quits, an excellent choice for winding down would be the 1747 Pub at Reynolds Tavern. They have both indoor and outdoor (heated) seating and feature good food, craft selections, and a laid back atmosphere. While the early closing hours due to the Pandemic have been rescinded, it would be wise to check websites or call the places you plan to stop if you have questions about the hours.
A little worn out or perhaps a little shit faced? You can always skip a few of the stops and finish up on your next trip to Annapolis. It’s a great town to visit so no need to rush it.
More of my favorite pictures from Annapolis:
And of course a picture of a “Cool Guy” slamming beers with friends on the patio at Stan and Joe’s.
