Destination Main Streets

Annapolis, Maryland

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You can say a lot about Annapolis. Seaport. State Capital. College town. But did you know that it contains one of the largest collections of 18th century structures in the nation? And much of those structures are still being used today the way they were intended hundreds of years ago. For example, the State House, where the Maryland General Assembly meets, is the oldest in continuous use in the nation.

But right outside the State House is an exciting city with a dizzying array of shops, restaurants, and entertainment. Just off the Chesapeake Bay, Annapolis is a seaport which can make for an interesting mix of characters. You can see students from St. John's College or midshipmen in uniform from the Naval Academy walking about town. Or you can listen in on lawmakers just one booth away from where you're eating at a local pub. At the city dock, boaters line up their yachts in what is known as "ego alley." It's this kind of excitement that makes Annapolis one of Maryland's top tourist destinations.

Annapolis is located in Anne Arundel County, Maryland and is approximately 22 miles east of Washington, DC, 26 miles south of Baltimore, Maryland, and 128 miles from Philadelphia, Pennsylvania. The heart of downtown Annapolis is located on Main Street running from Church Circle all the way to and around the Annapolis City Dock. Retail and dining can also be found on West Street, State Circle, and Maryland Avenue. Other Main Street communities worth checking out in the Baltimore-Washington corridor include Ellicott City, Sykesville, Bethesda, and Kensington.

Photo Gallery Tour

We start our tour of Annapolis, Maryland on West Street.  We'll head east towards the center of town and the Annapolis City Dock.  In the distance you can St. Anne's Parish and the Maryland State House.
We start our tour of Annapolis, Maryland on West Street. We'll head east towards the center of town and the Annapolis City Dock. In the distance you can St. Anne's Parish and the Maryland State House.
West Street has undergone quite a revival in recent years with many new restaurants, galleries and shops.  West Street, Maryland Avenue, State Circle, and of course, Main Street itself are the primary Main Streets in Annapolis.
West Street has undergone quite a revival in recent years with many new restaurants, galleries and shops. West Street, Maryland Avenue, State Circle, and of course, Main Street itself are the primary Main Streets in Annapolis.
No parking along this side of West Street allows for an excellent shot of the renovated historic buildings that are now shops, restaurants, and even an Escape Room.
No parking along this side of West Street allows for an excellent shot of the renovated historic buildings that are now shops, restaurants, and even an Escape Room.
More shops, businesses and a wine room along West Street.  Also notice the brick paved street.
More shops, businesses and a wine room along West Street. Also notice the brick paved street.
The Rams Head Tavern is a restaurant and bar and also a venue for national touring acts that come to town.
The Rams Head Tavern is a restaurant and bar and also a venue for national touring acts that come to town.
The blue brick building is is the Annapolis Visitors Center.  They also have a parking garage and bathrooms.  In fact, this is where I normally park when I come to Annapolis.  Great place to start your trip and you can park just on the outskirts of town and use their facilities after a long drive.  The address is 26 West Street, Annapolis Maryland.
The blue brick building is is the Annapolis Visitors Center. They also have a parking garage and bathrooms. In fact, this is where I normally park when I come to Annapolis. Great place to start your trip and you can park just on the outskirts of town and use their facilities after a long drive. The address is 26 West Street, Annapolis Maryland.
We approach Church Circle.  This is the Circuit Court for Anne Arundel County.  Annapolis is not just the State Capital of Maryland but also the Anne Arundel County Seat.
We approach Church Circle. This is the Circuit Court for Anne Arundel County. Annapolis is not just the State Capital of Maryland but also the Anne Arundel County Seat.
Just past State Circle, we reach Main Street where we'll find plenty more shops and businesses.  Looming over the rooftops is the Maryland State House.
Just past State Circle, we reach Main Street where we'll find plenty more shops and businesses. Looming over the rooftops is the Maryland State House.
The Maryland Inn is a Bed & Breakfast at the intersection of Main Street and Church Circle that also features the Treaty of Paris restaurant.
The Maryland Inn is a Bed & Breakfast at the intersection of Main Street and Church Circle that also features the Treaty of Paris restaurant.
We continue heading east walking down towards the water along Main Street.
We continue heading east walking down towards the water along Main Street.
An eclectic array of shops occupy the historic buildings, selling clothing, jewelry, and even comics.
An eclectic array of shops occupy the historic buildings, selling clothing, jewelry, and even comics.
The street plan of Annapolis was set up on a Baroque pattern with various circles and streets that spoked off of those circles.  The steps on the right side of this picture lead up to nearby State Circle.
The street plan of Annapolis was set up on a Baroque pattern with various circles and streets that spoked off of those circles. The steps on the right side of this picture lead up to nearby State Circle.
More shops and businesses along Main Street, including clothing stores, book stores, and an ice cream shop.
More shops and businesses along Main Street, including clothing stores, book stores, and an ice cream shop.
Newer brick buildings that replaced buildings wiped out in fires, blend in with older historic buildings.
Newer brick buildings that replaced buildings wiped out in fires, blend in with older historic buildings.
Here is another view of the newer buildings that are designed to blend in with the historic district.
Here is another view of the newer buildings that are designed to blend in with the historic district.
We head past more shops as we continue down Main Street towards the harbor.
We head past more shops as we continue down Main Street towards the harbor.
More shops and also a restaurant at the intersection of Main Street and Conduit Street.
More shops and also a restaurant at the intersection of Main Street and Conduit Street.
Here is a long view looking west back up the hill in the direction we came in.  We can see some of the shops have a touristy feel serving the visitors that come to Annapolis, such as the one selling T-shirts.
Here is a long view looking west back up the hill in the direction we came in. We can see some of the shops have a touristy feel serving the visitors that come to Annapolis, such as the one selling T-shirts.
An eclectic mix of boutiques, restaurants, and even a deli serving crab cakes, a Maryland favorite.
An eclectic mix of boutiques, restaurants, and even a deli serving crab cakes, a Maryland favorite.
Across the street are more shops as well as a bank.
Across the street are more shops as well as a bank.
Along Main Street we see shops, including one selling souvenirs and apparel aimed at tourists.
Along Main Street we see shops, including one selling souvenirs and apparel aimed at tourists.
We reach the corner of Main Street and Francis Street.  This is a view looking west.  Main Street is a spoke off of Church Circle which surrounds St. Anne's Parish while Francis Street is a small side street that is a spoke off of State Circle which surrounds the Maryland State House.
We reach the corner of Main Street and Francis Street. This is a view looking west. Main Street is a spoke off of Church Circle which surrounds St. Anne's Parish while Francis Street is a small side street that is a spoke off of State Circle which surrounds the Maryland State House.
If we walk up Francis Street a little bit and zoom in we can get a better view of the Maryland State House.
If we walk up Francis Street a little bit and zoom in we can get a better view of the Maryland State House.
We continue back down Main Street past the various high end galleries and boutiques.
We continue back down Main Street past the various high end galleries and boutiques.
More shops along Main Street.  Here you can see some tourists make their way through the heart of downtown Annapolis.
More shops along Main Street. Here you can see some tourists make their way through the heart of downtown Annapolis.
A Jimmy John's and an Irish gift shop.  There had been some controversy over the last few years about whether or not letting chains into the historic district of Annapolis would hurt the charm of the area.
A Jimmy John's and an Irish gift shop. There had been some controversy over the last few years about whether or not letting chains into the historic district of Annapolis would hurt the charm of the area.
A clothing store and an ice cream shop along Main Street.
A clothing store and an ice cream shop along Main Street.
More shops and even a frozen yogurt place at the corner of Main Street and Gorman Street.
More shops and even a frozen yogurt place at the corner of Main Street and Gorman Street.
At this point, we're getting closer to the waterfront and the Annapolis City Dock.
At this point, we're getting closer to the waterfront and the Annapolis City Dock.
The Black Dog General Store is a chain we have seen mostly in New England but here is a location in Annapolis.
The Black Dog General Store is a chain we have seen mostly in New England but here is a location in Annapolis.
This is another store geared for the many tourists that come to Annapolis every year.
This is another store geared for the many tourists that come to Annapolis every year.
O'Brien's takes up this large historic building along Main Street.  Notice the sailor holding the bushel of crabs on the left side of the picture?  Nothing says Annapolis more, as the city is home to the U.S. Naval Academy.
O'Brien's takes up this large historic building along Main Street. Notice the sailor holding the bushel of crabs on the left side of the picture? Nothing says Annapolis more, as the city is home to the U.S. Naval Academy.
More shops and restaurants as we get to the intersection of Main Street and Green Street.
More shops and restaurants as we get to the intersection of Main Street and Green Street.
The Goodman Building was built in 1909 and was the site of Aaron Lee Goodman's shop.  Today the bottom floor is occupied by retailers while the second story is home to Buddy's Crab & Ribs.
The Goodman Building was built in 1909 and was the site of Aaron Lee Goodman's shop. Today the bottom floor is occupied by retailers while the second story is home to Buddy's Crab & Ribs.
As we continue heading east Main Street meets Compromise Street and the intersection forms a roundabout.  Across from the roundabout is the Historic Annapolis Museum & Store.  The red and white building on the right is on Green Street and is called Hobo and sells handbags, wallets, and accessories.
As we continue heading east Main Street meets Compromise Street and the intersection forms a roundabout. Across from the roundabout is the Historic Annapolis Museum & Store. The red and white building on the right is on Green Street and is called Hobo and sells handbags, wallets, and accessories.
At the corner of Main Street and Compromise Street is the Annapolis Summer Garden Theatre, a longtime community theater led by volunteers showcasing musicals on an outdoor stage.
At the corner of Main Street and Compromise Street is the Annapolis Summer Garden Theatre, a longtime community theater led by volunteers showcasing musicals on an outdoor stage.
Here is a view of the roundabout where Main Street and Compromise Street meet.  To the right is the Annapolis City Dock where Spa Creek comes into the city.  Shops and restaurants in historic buildings surround the Annapolis waterfront.
Here is a view of the roundabout where Main Street and Compromise Street meet. To the right is the Annapolis City Dock where Spa Creek comes into the city. Shops and restaurants in historic buildings surround the Annapolis waterfront.
Here is a closer view of the Annapolis City Dock.  Throughout the year, visitors bring their yachts into the harbor, giving this stretch the name Ego Alley.  It's great for people watching.  Annapolis was founded on the Severn River and Spa Creek is the waterway that leads into the heart of the city.
Here is a closer view of the Annapolis City Dock. Throughout the year, visitors bring their yachts into the harbor, giving this stretch the name Ego Alley. It's great for people watching. Annapolis was founded on the Severn River and Spa Creek is the waterway that leads into the heart of the city.
Close to the waterfront is the Kunta Kinte-Alex Haley Memorial, dedicated in three parts between 1997 and 2002.
Close to the waterfront is the Kunta Kinte-Alex Haley Memorial, dedicated in three parts between 1997 and 2002.
The Market House features various quick service food stalls and has been serving the area in one form or another since 1788.
The Market House features various quick service food stalls and has been serving the area in one form or another since 1788.
We'll walk around the Annapolis City Dock and check out the businesses on the other side, including these on Dock Street.
We'll walk around the Annapolis City Dock and check out the businesses on the other side, including these on Dock Street.
A sailor gives directions to tourists.  We're getting close to the entrance to the U.S. Naval Academy.
A sailor gives directions to tourists. We're getting close to the entrance to the U.S. Naval Academy.
This building contains the Annapolis Harbormaster's Offices.  Here you'll also find more bathrooms and another Visitor Center.  There is another public parking lot down here, but the parking and the traffic down here can get crazy.
This building contains the Annapolis Harbormaster's Offices. Here you'll also find more bathrooms and another Visitor Center. There is another public parking lot down here, but the parking and the traffic down here can get crazy.
More shops at the corner of Dock Street and Craig Street.
More shops at the corner of Dock Street and Craig Street.
There is even a small mall with more shops inside.
There is even a small mall with more shops inside.
And if you continue down Craig Street you'll come to one of the gates to the U.S. Naval Academy.
And if you continue down Craig Street you'll come to one of the gates to the U.S. Naval Academy.
We continue our trip around the dock and find other businesses we would expect to see around the waterfront such as the Annapolis Yacht Company.
We continue our trip around the dock and find other businesses we would expect to see around the waterfront such as the Annapolis Yacht Company.
We head back up the way we came on Dock Street until it turns into Market Space and find more restaurants, many serving visitors that come in by boat.
We head back up the way we came on Dock Street until it turns into Market Space and find more restaurants, many serving visitors that come in by boat.
We turn left and now we are behind the Market House we visited earlier.  This street bordering the Market House is known as Market Space.
We turn left and now we are behind the Market House we visited earlier. This street bordering the Market House is known as Market Space.
Here are more shops and restaurants along Market Space.  To the left and out of the picture is the Market House from before.
Here are more shops and restaurants along Market Space. To the left and out of the picture is the Market House from before.
More shops and businesses at the intersection of Market Space and Fleet Street.
More shops and businesses at the intersection of Market Space and Fleet Street.
A view looking northwest up Fleet Street.  We see a few shops on this side street as well.
A view looking northwest up Fleet Street. We see a few shops on this side street as well.
Back on Market Space we find more shops, including a gift shop with a flair for Maryland style.
Back on Market Space we find more shops, including a gift shop with a flair for Maryland style.
More businesses along Market Space, including a coffee shop and ice cream shop, depending on your mood and the weather?  Main Street is just up ahead.  We've now made a complete circle.
More businesses along Market Space, including a coffee shop and ice cream shop, depending on your mood and the weather? Main Street is just up ahead. We've now made a complete circle.
We'll head up to State Circle now where we will find more businesses located in the historic properties around the State House.  This is the State House Inn, a Bed & Breakfast on State Circle.  On the back side is Main Street, which passes behind this side of State Circle.
We'll head up to State Circle now where we will find more businesses located in the historic properties around the State House. This is the State House Inn, a Bed & Breakfast on State Circle. On the back side is Main Street, which passes behind this side of State Circle.
We continue our way around State Circle and come across more shops, including these at the corner of State Circle and Francis Street.
We continue our way around State Circle and come across more shops, including these at the corner of State Circle and Francis Street.
If we look up, we can see the Maryland State House on the left.  Completed in 1779, this is the oldest U.S. State Capitol in continuous legislative use.  To the right is the Old Treasury Building.  Built in 1735-36 as a treasury for the Commissioners for Emitting Bills of Credit, it is the oldest public building in Annapolis.
If we look up, we can see the Maryland State House on the left. Completed in 1779, this is the oldest U.S. State Capitol in continuous legislative use. To the right is the Old Treasury Building. Built in 1735-36 as a treasury for the Commissioners for Emitting Bills of Credit, it is the oldest public building in Annapolis.
Here is another Bed & Breakfast.  This one is the Governor Calvert House.
Here is another Bed & Breakfast. This one is the Governor Calvert House.
We continue heading north along State Circle, making a counter-clockwise loop around the Circle past more shops and sidewalk cafes.
We continue heading north along State Circle, making a counter-clockwise loop around the Circle past more shops and sidewalk cafes.
This is the corner of State Circle and Maryland Avenue.  Now we will head northeast along Maryland Avenue, another small Main Street of Annapolis.
This is the corner of State Circle and Maryland Avenue. Now we will head northeast along Maryland Avenue, another small Main Street of Annapolis.
Across the street on the other corner of State Circle and Maryland Avenue, we see more shops and boutiques.
Across the street on the other corner of State Circle and Maryland Avenue, we see more shops and boutiques.
Coffee shops, boutiques, gift shops, and stores selling records fill the historic buildings along Maryland Avenue.
Coffee shops, boutiques, gift shops, and stores selling records fill the historic buildings along Maryland Avenue.
Visitors take pictures in front of the historic buildings.  Maryland Avenue can be quieter than Main Street but there are still shops and restaurants here worth checking out.
Visitors take pictures in front of the historic buildings. Maryland Avenue can be quieter than Main Street but there are still shops and restaurants here worth checking out.
Businessmen (maybe lawmakers?) chat in front of an Irish Pub not too far from the State House.
Businessmen (maybe lawmakers?) chat in front of an Irish Pub not too far from the State House.
A row of businesses occupy historic buildings along quiet Maryland Avenue.
A row of businesses occupy historic buildings along quiet Maryland Avenue.
The State House rises in the background over the shops on Maryland Avenue.
The State House rises in the background over the shops on Maryland Avenue.
We make it to the intersection of Maryland Avenue and Prince George Street.  This building on the corner is known as the Opera House.
We make it to the intersection of Maryland Avenue and Prince George Street. This building on the corner is known as the Opera House.
This old church sits across from the Opera House.  Today it is rented out for office space.  If we continue down Maryland Avenue we encounter a few more shops.  But this has been quite a journey and our tour has come to an end.
This old church sits across from the Opera House. Today it is rented out for office space. If we continue down Maryland Avenue we encounter a few more shops. But this has been quite a journey and our tour has come to an end.

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