Destination Main Streets

Chesapeake City, Maryland

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Chesapeake City is Maryland's gateway to the Eastern Shore. Slicing the city in half is the Chesapeake and Delaware Canal, which serves as the unofficial northern boundary of the Eastern Shore. The canal was built to connect the Chesapeake Bay with the Delaware River to create an important shipping route between Philadelphia and Baltimore.

Today, Maryland Route 213 is also a major transportation corridor, connecting Chesapeake City to the rest of the world. But it's been a mixed blessing. The Chesapeake City Bridge, carrying Route 213 traffic over the C&D Canal is so large and tall that it almost completely travels over the city itself, bypassing it altogether. When the bridge first opened in 1949, a sudden loss in traffic caused a decline in Chesapeake City's economy. However, it's that same route that today brings many day-trippers to the city, which is now known for its dozens of antique stores, gift shops, restaurants, bed & breakfasts, and other attractions.

Chesapeake City's Main Street is Bohemia Avenue. Retail and dining can also be found on Second, Third, and George Streets. But make a point of walking down to the shore and enjoy the scenic waterfront views. You can even watch the cargo ships moving up and down the canal as they pass under the Chesapeake City Bridge. Chesapeake City is about 63 miles from Baltimore, Maryland, 56 miles from Philadelphia, Pennsylvania, and 99 miles from Washington, DC. Chesapeake City is located in Cecil County in Maryland's Upper Eastern Shore region. Other nearby Main Street communities worth checking out include Chestertown, North East, and Havre de Grace.

Photo Gallery

Before we start our tour of Chesapeake City, this is a view from the Chesapeake City Bridge, which travels over town.  I took this picture almost ten years before my most recent visit to the area.  I wish I could have gotten a new shot but renovations on the bridge had traffic closed to pedestrians.
Before we start our tour of Chesapeake City, this is a view from the Chesapeake City Bridge, which travels over town. I took this picture almost ten years before my most recent visit to the area. I wish I could have gotten a new shot but renovations on the bridge had traffic closed to pedestrians.
We'll start our tour of Chesapeake City at the intersection of Bohemia Avenue and Third Street.  Bohemia Avenue is Chesapeake City's Main Street.  You'll find shops, restaurants, and plenty of Bed & Breakfasts such as this one with the distinctive sign.  It looks like some sort of pirate swinging down from the balcony.
We'll start our tour of Chesapeake City at the intersection of Bohemia Avenue and Third Street. Bohemia Avenue is Chesapeake City's Main Street. You'll find shops, restaurants, and plenty of Bed & Breakfasts such as this one with the distinctive sign. It looks like some sort of pirate swinging down from the balcony.
Across the street is the Chesapeake City United Methodist Charge at Trinity United Methodist Church.
Across the street is the Chesapeake City United Methodist Charge at Trinity United Methodist Church.
Here are some of the shops and restaurants along Bohemia Avenue.  We are heading northeast towards the Chesapeake and Delaware Canal.
Here are some of the shops and restaurants along Bohemia Avenue. We are heading northeast towards the Chesapeake and Delaware Canal.
On the left is another shop in a well-maintained historic structure.  On the right is a building with a lot of potential.  If you look carefully in the first picture from the bridge, you can just make these two out.
On the left is another shop in a well-maintained historic structure. On the right is a building with a lot of potential. If you look carefully in the first picture from the bridge, you can just make these two out.
We continue along Bohemia Avenue where we find more Bed & Breakfasts.  All of these structures are part of the South Chesapeake City Historic District.
We continue along Bohemia Avenue where we find more Bed & Breakfasts. All of these structures are part of the South Chesapeake City Historic District.
Here are some more Bed & Breakfasts as we continue to make our way towards the C&D Canal.  When the canal was built in the early ninteenth century it divided the town in half.  The Historic Distict is on the south side of the canal.  Also, after the canal was built the town changed its name from Bohemia to Chesapeake City.
Here are some more Bed & Breakfasts as we continue to make our way towards the C&D Canal. When the canal was built in the early ninteenth century it divided the town in half. The Historic Distict is on the south side of the canal. Also, after the canal was built the town changed its name from Bohemia to Chesapeake City.
We make it to the intersection of Bohemia Avenue and Second Street.  Now you know where Bohemia Avenue got it's name (it was once the name of the town).  In the background you can see the ever present bridge looming overhead.
We make it to the intersection of Bohemia Avenue and Second Street. Now you know where Bohemia Avenue got it's name (it was once the name of the town). In the background you can see the ever present bridge looming overhead.
At the intersection of Bohemia Avenue and Second Street you have the Town Hall, and in the distance, you can see and antique store that also sells cards and other collectibles.
At the intersection of Bohemia Avenue and Second Street you have the Town Hall, and in the distance, you can see and antique store that also sells cards and other collectibles.
Across the street from the Town Hall is an old bank building, which also used to be the Town Hall.  Notice the bars on the windows.  In the distance, you can see the bridge looming in the background.  Always a presence in the city.
Across the street from the Town Hall is an old bank building, which also used to be the Town Hall. Notice the bars on the windows. In the distance, you can see the bridge looming in the background. Always a presence in the city.
On the left is a general store that was first established in 1861.  The home on the right was built in 1876 in the Victorian Gothic style and is today a Bed & Breakfast.
On the left is a general store that was first established in 1861. The home on the right was built in 1876 in the Victorian Gothic style and is today a Bed & Breakfast.
Here is a closer look at that Bed & Breakfast, The Inn at the Canal.  The small annex to the left was for the second owner to use as an office.  At one time, you were not allowed to run a business out of your home.  It was not uncommon to see many structures like this throughout town.  Today this is the only one remaining, and it is currently being used as a small shop.
Here is a closer look at that Bed & Breakfast, The Inn at the Canal. The small annex to the left was for the second owner to use as an office. At one time, you were not allowed to run a business out of your home. It was not uncommon to see many structures like this throughout town. Today this is the only one remaining, and it is currently being used as a small shop.
As we head closer to the water, we see another view of the general store along with the Masonic Hall on the left built in the Romanesque style.  Today a photography studio and gallery occupies a portion of the Masonic Hall.  See the wooden walkway to the right of the Masonic Hall?  Those lead to public restrooms.
As we head closer to the water, we see another view of the general store along with the Masonic Hall on the left built in the Romanesque style. Today a photography studio and gallery occupies a portion of the Masonic Hall. See the wooden walkway to the right of the Masonic Hall? Those lead to public restrooms.
If we keep heading northeast towards the water we come to Pell Gardens Park, which sits on the water.  There is a bandshell and gazebo, and it is also used for weddings.
If we keep heading northeast towards the water we come to Pell Gardens Park, which sits on the water. There is a bandshell and gazebo, and it is also used for weddings.
I'll let the sign speak for itself, but you can read the story of the bridge that use to be here before the newer larger one that rises over the area.
I'll let the sign speak for itself, but you can read the story of the bridge that use to be here before the newer larger one that rises over the area.
We haven't even looked at the other side of Bohemia Avenue in a while, which as you can see, also has some shops, restaurants and inns.  The building on the far right is called The Bayard House and is believed to be the oldest house in Chesapeake City.
We haven't even looked at the other side of Bohemia Avenue in a while, which as you can see, also has some shops, restaurants and inns. The building on the far right is called The Bayard House and is believed to be the oldest house in Chesapeake City.
Here's another view of those same set of houses from a different angle.
Here's another view of those same set of houses from a different angle.
Just past the Bayard House we come to the C&D Canal waterfront.  In the distance, we can see the Chesapeake City Bridge.  If you look carefully at the bridge, you can see that it is undergoing renovations.  The canal connects shipping traffic between the Chesapeake Bay and the Delaware River.
Just past the Bayard House we come to the C&D Canal waterfront. In the distance, we can see the Chesapeake City Bridge. If you look carefully at the bridge, you can see that it is undergoing renovations. The canal connects shipping traffic between the Chesapeake Bay and the Delaware River.
On the other side of the canal, on the north side of Chesapeake City, is the popular and huge Schaffer's Canal House, which is hard to miss from the south side of Chesapeake City.  They even have a marina for your boat.
On the other side of the canal, on the north side of Chesapeake City, is the popular and huge Schaffer's Canal House, which is hard to miss from the south side of Chesapeake City. They even have a marina for your boat.
As we circle around Bohemia Avenue and head east, we come across this quaint little cottage on the water.
As we circle around Bohemia Avenue and head east, we come across this quaint little cottage on the water.
Next door there's a small place to get some ice cream with some picnic tables where you can enjoy it right on the water.
Next door there's a small place to get some ice cream with some picnic tables where you can enjoy it right on the water.
As we come to the end of Bohemia Avenue, we see another large restaurant with a marina.  This one, The Chesapeake Inn, is on the south side of Chesapeake City.
As we come to the end of Bohemia Avenue, we see another large restaurant with a marina. This one, The Chesapeake Inn, is on the south side of Chesapeake City.
Now we're going to circle around and head northwest on First Street.  On the right is The Ship Watch Inn, which gets its name because of its view of the C&D Canal just on the other side.
Now we're going to circle around and head northwest on First Street. On the right is The Ship Watch Inn, which gets its name because of its view of the C&D Canal just on the other side.
We'll turn left and head southwest down George Street away from the canal.  This street runs parallel to Bohemia Avenue and also has shops and businesses along the way.
We'll turn left and head southwest down George Street away from the canal. This street runs parallel to Bohemia Avenue and also has shops and businesses along the way.
This is a view looking back in the direction from which we came.  In the distance, you can see the C&D Canal.  Notice the name of the bakery uses Chesapeake City's former name.
This is a view looking back in the direction from which we came. In the distance, you can see the C&D Canal. Notice the name of the bakery uses Chesapeake City's former name.
There aren't as many businesses along George Street but you will find plenty of restored and well maintained historic houses.  In the background, you can see the Chesapeake City Bridge to the west.
There aren't as many businesses along George Street but you will find plenty of restored and well maintained historic houses. In the background, you can see the Chesapeake City Bridge to the west.
Here are some restored houses, some of which are being used for businesses along George Street.
Here are some restored houses, some of which are being used for businesses along George Street.
We continue heading southwest along George Street toward where we started our tour.  Basically, we're making a big loop, but it's nice to check out the houses while we're doing it.
We continue heading southwest along George Street toward where we started our tour. Basically, we're making a big loop, but it's nice to check out the houses while we're doing it.
This is the corner of George Street and Third Street. We started our tour at the corner of Bohemia Avenue and Third Street, so we have almost completed the loop.  Here we see a studio and gallery.
This is the corner of George Street and Third Street. We started our tour at the corner of Bohemia Avenue and Third Street, so we have almost completed the loop. Here we see a studio and gallery.
We end our tour with one last house.  This is the Steele-Davis House, and was built circa 1872 in the Federal-Italianate style.  The three story front section was built by Joseph Hedrick, the official of the C&D Canal. In 1879, Mr. Hedrick was caught using canal funds to finance work on the house.  He left the country and the house was sold at public auction.
We end our tour with one last house. This is the Steele-Davis House, and was built circa 1872 in the Federal-Italianate style. The three story front section was built by Joseph Hedrick, the official of the C&D Canal. In 1879, Mr. Hedrick was caught using canal funds to finance work on the house. He left the country and the house was sold at public auction.

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