Destination Main Streets

Chestertown, Maryland

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On the banks of the Chester River lies what seems to be a quiet, unassuming town. You wouldn't even notice Chestertown, Maryland unless you took another look. However, in the eighteenth century, Chestertown was the second largest shipping port in the state of Maryland. Today, it's second only to Annapolis in its concentration of historic eighteenth century homes. Some of the finest examples are the large Georgian homes that line the Chester River along the south side of town, many built by wealthy shippers. Chestertown's good fortune is owed to the fact that the city was mostly spared during the American Revolution.

Through the years, Chestertown's shipping industry dried up. However, other institutions have moved in to fill the void in the city's economy. Chestertown is home to Washington College, the tenth oldest liberal arts college to be chartered in the nation and the oldest college in Maryland. Chestertown also serves as the Kent County Seat. It's enough to keep this small town thriving so many years after its hey day. You'll find book stores, art galleries, boutiques, cafes, and so much more.

Chestertown has two Main Streets that intersect with each other—High Street and Cross Street. This would also be a good intersection to set on your GPS for locating the heart of town. The city is a must stop for anyone touring Maryland's upper Chesapeake region. The drive itself is very scenic and an attraction in itself. Other nearby Main Streets to check out in the upper Chesapeake region include Chesapeake City and North East. Chestertown is about 75 miles from either Baltimore, Maryland or Washington, DC, and about 87 miles from Philadelphia, Pennsylvania.

Photo Gallery

We start our tour of Chestertown, Maryland at the intersection of Cross Street and Maple Avenue.  This is the Kent County Visitors Center.  Cross Street is one of the Main Streets in Chestertown along with High Street.  We'll continue heading southwest into town along Cross Street.
We start our tour of Chestertown, Maryland at the intersection of Cross Street and Maple Avenue. This is the Kent County Visitors Center. Cross Street is one of the Main Streets in Chestertown along with High Street. We'll continue heading southwest into town along Cross Street.
As we continue walking down Cross Street towards the center of town we pass by the Town Hall just next door to the Kent County Visitors Center.
As we continue walking down Cross Street towards the center of town we pass by the Town Hall just next door to the Kent County Visitors Center.
And a little further down and across the street is the Kent County Courthouse.  Chestertown is the County Seat for Kent County, Maryland.
And a little further down and across the street is the Kent County Courthouse. Chestertown is the County Seat for Kent County, Maryland.
Now we come to the Emmanual Episcopal Church.  The congregation dates all the way back to 1706.  The building itself dates back to 1767.
Now we come to the Emmanual Episcopal Church. The congregation dates all the way back to 1706. The building itself dates back to 1767.
Okay, if anyone knows the story behind this, please let me know.  The back says, "In Memory of James Alfred Pearce U.S. Senator from Maryland." Seems like an interesting way to memorialize someone though.
Okay, if anyone knows the story behind this, please let me know. The back says, "In Memory of James Alfred Pearce U.S. Senator from Maryland." Seems like an interesting way to memorialize someone though.
Memorial Row is a park at the corner of Cross Street and High Street that features many monuments dedicated to several wars America has fought in over the years.
Memorial Row is a park at the corner of Cross Street and High Street that features many monuments dedicated to several wars America has fought in over the years.
Across High Street on the corner of High and Cross is this bank building.  We've made it to the heart of town.  We'll continue down Cross Street first before exploring High Street further.
Across High Street on the corner of High and Cross is this bank building. We've made it to the heart of town. We'll continue down Cross Street first before exploring High Street further.
We continue heading southwest along Cross Street.  Most of the businesses on Cross Street are on this side of High Street.  Here you can see an example of the historic architecture you'll find around Chestertown.
We continue heading southwest along Cross Street. Most of the businesses on Cross Street are on this side of High Street. Here you can see an example of the historic architecture you'll find around Chestertown.
Shops, boutiques, and galleries line Cross Street while bricks cover the sidewalks.
Shops, boutiques, and galleries line Cross Street while bricks cover the sidewalks.
Across the street a store selling needlepoint designs is located in a colonial style house.
Across the street a store selling needlepoint designs is located in a colonial style house.
On the left is Sandbox, and art gallery that collaborates with Washington College, which is located in Chestertown.  Washington College is the tenth oldest liberal arts college to be chartered in the nation and the oldest college in Maryland.
On the left is Sandbox, and art gallery that collaborates with Washington College, which is located in Chestertown. Washington College is the tenth oldest liberal arts college to be chartered in the nation and the oldest college in Maryland.
As we continue down Cross Street we come across another art gallery.  Chestertown has a flourishing arts scene.  It doesn't hurt that it's also a college town.  I'll admit there's a lot more action here now than there was the last time I was here ten years ago.
As we continue down Cross Street we come across another art gallery. Chestertown has a flourishing arts scene. It doesn't hurt that it's also a college town. I'll admit there's a lot more action here now than there was the last time I was here ten years ago.
If we pull back we can see that the art gallery is in a former volunteer fire house that was built in 1908.  It was constructed with blocks that the volunteer fire fighters built themselves.  They did a great job.  Check out that cupola!
If we pull back we can see that the art gallery is in a former volunteer fire house that was built in 1908. It was constructed with blocks that the volunteer fire fighters built themselves. They did a great job. Check out that cupola!
This is a view of Cross Street and Cannon Street, looking back in the direction we just came from.  At the corner is the Janes United Methodist Church.
This is a view of Cross Street and Cannon Street, looking back in the direction we just came from. At the corner is the Janes United Methodist Church.
Catty-corner from the church, this historic building is now a real estate office.
Catty-corner from the church, this historic building is now a real estate office.
If we continue down Cross Street we head of downtown, but there's still more to see.  This old mill has been converted into multiple shops.
If we continue down Cross Street we head of downtown, but there's still more to see. This old mill has been converted into multiple shops.
And this looks like an old train station but it too has been converted to more retail.  It sits along a rails to trails project now called the Chestertown Rail Trail.
And this looks like an old train station but it too has been converted to more retail. It sits along a rails to trails project now called the Chestertown Rail Trail.
More signs of Chestertown's railroad history.  Here is some old passenger cars and a caboose sitting alongside a large mill.  We've reached the outskirts of town so now we'll turn back and head into town again.
More signs of Chestertown's railroad history. Here is some old passenger cars and a caboose sitting alongside a large mill. We've reached the outskirts of town so now we'll turn back and head into town again.
Now we'll doubleback and head down High Street, Chestertown's other Main Street.  We'll start on the northwest end and head southeast towards the Chester River waterfront.
Now we'll doubleback and head down High Street, Chestertown's other Main Street. We'll start on the northwest end and head southeast towards the Chester River waterfront.
As we continue heading down High Street, we pass more businesses, including a pharmacy and Bloomin' Wild a floral boutique.
As we continue heading down High Street, we pass more businesses, including a pharmacy and Bloomin' Wild a floral boutique.
Here's another view of the building we were just looking at.  From this angle we can see a mural painted on the wall pointing down to more businesses behind High Street.
Here's another view of the building we were just looking at. From this angle we can see a mural painted on the wall pointing down to more businesses behind High Street.
After taking this slight detour, we find a few more shops and businesses along Cannon Street, which runs parallel to High Street.
After taking this slight detour, we find a few more shops and businesses along Cannon Street, which runs parallel to High Street.
Notice that art gallery in the previous picture (the yellow house on the right)?  This is the view behind the house.  Several of its outbuildings are also used for gallery space.
Notice that art gallery in the previous picture (the yellow house on the right)? This is the view behind the house. Several of its outbuildings are also used for gallery space.
This is another restored house on Cannon Street that has been converted into a business.  On the left, you can see the art gallery from the previous pictures.
This is another restored house on Cannon Street that has been converted into a business. On the left, you can see the art gallery from the previous pictures.
Also on Cannon Street is this natural foods grocery store.
Also on Cannon Street is this natural foods grocery store.
We make it back up to High Street and continue our trip southeast down toward the waterfront.  Notice the wide brick sidewalks.  I also like the sign under Poor Richards.  "Nothing Over A Million Dollars."
We make it back up to High Street and continue our trip southeast down toward the waterfront. Notice the wide brick sidewalks. I also like the sign under Poor Richards. "Nothing Over A Million Dollars."
This shop has more of a nautical theme, fitting for Chestertown's location on Maryland's Eastern Shore.  Although the building it's in doesn't appear to be historic.  Maybe something happened to the previous one.  A fire?
This shop has more of a nautical theme, fitting for Chestertown's location on Maryland's Eastern Shore. Although the building it's in doesn't appear to be historic. Maybe something happened to the previous one. A fire?
We continue heading southeast down High Street.  I did take several pictures in a row looking backwards, so the light was probably just agreeable in this direction.
We continue heading southeast down High Street. I did take several pictures in a row looking backwards, so the light was probably just agreeable in this direction.
We make it to the corner of High Street and Cross Street (again).  This building is referred to as Bordley Corner, named after the family that owned a men's store here for many years.  See, I read the plaque.  For many years, it was also a book store.  Today it is the Historical Society of Kent County.
We make it to the corner of High Street and Cross Street (again). This building is referred to as Bordley Corner, named after the family that owned a men's store here for many years. See, I read the plaque. For many years, it was also a book store. Today it is the Historical Society of Kent County.
Across the street is Fountain Park, named after this fountain in the center of the park.  You can see the row of businesses we just walked past.  On Saturdays in the spring, summer, and fall this is the home to the Chestertown Farmers' & Artisans' Market.
Across the street is Fountain Park, named after this fountain in the center of the park. You can see the row of businesses we just walked past. On Saturdays in the spring, summer, and fall this is the home to the Chestertown Farmers' & Artisans' Market.
Continuing down High Street we see some more shops, including this music school and store.
Continuing down High Street we see some more shops, including this music school and store.
Here's another view of the same stretch.  You can see an art gallery next door to the music school and store.
Here's another view of the same stretch. You can see an art gallery next door to the music school and store.
Looking for a place to stay in Chestertown?  The White Swan Tavern is a Bed & Breakfast that can trace its roots back to 1733 when the front portion of the present structure was first built.
Looking for a place to stay in Chestertown? The White Swan Tavern is a Bed & Breakfast that can trace its roots back to 1733 when the front portion of the present structure was first built.
Well, as the sign says, we're getting closer to the river.  I promise it won't be long.
Well, as the sign says, we're getting closer to the river. I promise it won't be long.
Across the street from the businesses we were just looking at was Memorial Row, the park we saw earlier when we walked down Cross Street.  This small fountain was at the other far end of the row.  I thought I'd take a picture of it with the building in the background.
Across the street from the businesses we were just looking at was Memorial Row, the park we saw earlier when we walked down Cross Street. This small fountain was at the other far end of the row. I thought I'd take a picture of it with the building in the background.
We make it to the corner of High Street and Court Street, site of Stam's Hall, built in 1886.  The building really stands out.  Colin Stam built it with those intentions.  It was the site of the original location of his family's pharmacy, but it was also the first site of Chestertown's Town Hall, and also the site of the Lyceum Theatre.
We make it to the corner of High Street and Court Street, site of Stam's Hall, built in 1886. The building really stands out. Colin Stam built it with those intentions. It was the site of the original location of his family's pharmacy, but it was also the first site of Chestertown's Town Hall, and also the site of the Lyceum Theatre.
Next door the New Lyceum Theatre opened in 1928.  Today, it's the Garfield Center for the Arts at the Prince Theatre.  Next door, the Hotel Imperial is now a Bed & Breakfast part of the The Kitchen at the Imperial.
Next door the New Lyceum Theatre opened in 1928. Today, it's the Garfield Center for the Arts at the Prince Theatre. Next door, the Hotel Imperial is now a Bed & Breakfast part of the The Kitchen at the Imperial.
On the other side of High Street, we find more shops and businesses, including the current location of Stam's Pharmacy.
On the other side of High Street, we find more shops and businesses, including the current location of Stam's Pharmacy.
A peek inside shows Stam's Pharmacy is going strong but its decor and many of its touches are an earlier era.
A peek inside shows Stam's Pharmacy is going strong but its decor and many of its touches are an earlier era.
On the right, The Chestertown Bank of Maryland building was built in 1929.  It doesn't have that Georgian or Federalist brick feel to it that the other buildings around Chestertown have but it certainly feels like a bank building.
On the right, The Chestertown Bank of Maryland building was built in 1929. It doesn't have that Georgian or Federalist brick feel to it that the other buildings around Chestertown have but it certainly feels like a bank building.
We're almost to the end of the business district along High Street and we see some folks eating along a sidewalk cafe in front of an art gallery in this freshly restored building.
We're almost to the end of the business district along High Street and we see some folks eating along a sidewalk cafe in front of an art gallery in this freshly restored building.
Across the street is a gift shop selling some nautical themed products.
Across the street is a gift shop selling some nautical themed products.
If we continue down High Street a little ways we'll pass by some beautiful houses.  Chestertown is second only to Annapolis in its concentration of historic eighteenth century homes in Maryland.  Once we pass those houses, we reach the waterfront and the Kent River.  Just like I promised.
If we continue down High Street a little ways we'll pass by some beautiful houses. Chestertown is second only to Annapolis in its concentration of historic eighteenth century homes in Maryland. Once we pass those houses, we reach the waterfront and the Kent River. Just like I promised.
And of course, here's a shot of one of those houses.  Many of the most prominent homes in Chestertown look over the Kent River and you can get a look at them when you come down to the end of High Street.  This concludes our tour of Chestertown but doesn't have to end our tour of the Eastern Shore with many other towns in the area to explore.
And of course, here's a shot of one of those houses. Many of the most prominent homes in Chestertown look over the Kent River and you can get a look at them when you come down to the end of High Street. This concludes our tour of Chestertown but doesn't have to end our tour of the Eastern Shore with many other towns in the area to explore.

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