Skyscraper City Forum banner
1 - 11 of 11 Posts

·
Moderator
Joined
·
18,281 Posts
Discussion Starter · #1 ·
Chestertown is a colonial port town, settled in 1706 on the Chester River. It is the seat of Kent County, the original county on Maryland's Eastern Shore. The population is around 4700.

Chestertown was one of six Royal Ports of Entry in Maryland, which led to Chestertown growing as one of the Eastern Shore's main ports. In the mid-1700's, Chestertown was second only to Annapolis as the most important port in Maryland. Chestertown's importance is reflected in the large amount of colonial houses; many say Chestertown is second only to Annapolis again in terms of colonial architecture.

Chestertown's most famous event was the Chestertown Tea Party. In 1774, after hearing about the Boston Tea Party, residents threw tea into the Chester River, and stopped the sale, distribution, and consumption of tea in the town.


Chestertown's historic waterfront houses.



Looking down the Chester River towards Chestertown's dock facilities.



Looking down the Chester River.



Chestertown from the Maple Street Bridge, which crosses the Chester River into Queen Anne's County.



Houses on Water Street. The house in the middle, the Watkins House, dates back to 1739, and is believed to be the oldest house on Water Street. The houses on the left actually date back to the late 1800's, and replaced older houses on the site.



An old colonial garden, with a boat dock behind the house.



A house on Water Street.



Rowhouses on Water Street.



Houses along Water Street, facing the Chester River and across the street from the gardens of the Widehall mansion.



The Hynson-Ringgold House on Water Street, dating back to 1743.



Old wooden houses on Front Street.



Restaurants, antique stores, and other businesses on High Street. Stam's Hall, built in 1886, is on the left.



The Kent County Courthouse on Park Row, near Court Street and High Street. This courthouse was built in 1860.



The Kent County Courthouse.



These little buildings on Court Street were once lawyer's offices, back in the late 1870's after the building of the new courthouse across the street created demand for access to the center. They now serve as tiny houses.



The Hogans Building on Memorial Plaza, at Park Row. This building was built in the early 1830's, and was the meeting place for the Freemasons in Chestertown.



Businesses on High Street.



Houses on Queen Street.



Houses on Cannon Street at Queen Street.



Houses on Cannon Street.



Houses on Cannon Street near Front Street.



An old shipbuilder's mansion, built in 1857, at Front & Cannon Streets.



A house on High Stret near the Chester River.



Christ United Methodist Church on High Street.



Houses on High Street at Kent Street.



Chestertown Public School on HIgh Street, built in 1908.



Little houses on Church Alley.



Houses on Queen Street.



Businesses on High Street at Queen Street.



Businesses on Cross Street.




Chestertown is a nice colonial city that is unknown because it is second to Annapolis in Maryland, and because it is on Maryland's less popular Eastern Shore. Despite not getting much recognition, Chestertown is a still great place to visit and explore.
 

·
Old Fart
Joined
·
833 Posts
Sad to admit that even though I've lived in MD for over 25 years, I've never been to Chestertown. Lovely looking town, and now a must visit on my Maryland tour. Thanks for the pics Mark.
 

·
Moderator
Joined
·
18,281 Posts
Discussion Starter · #3 ·
Sad to admit that even though I've lived in MD for over 25 years, I've never been to Chestertown. Lovely looking town, and now a must visit on my Maryland tour. Thanks for the pics Mark.
Actually, my name is Matt. Maybe your doctor's office is also a must-visit?;)
 

·
Registered
Joined
·
5,517 Posts
Chestertown is a gem. If you like that, also take in Oxford and St Michaels. I believe that Oxford was the biggest metropolis in North America in 1680. It's still the biggest town on that peninsula...and the only town on that peninsula. All 3 towns get a pretty decent tourist trade, and Chestertown as a small but well regarded college, Washington College. Any of these towns make a good weekend retreat from busy cities are full of great old buildings and nice little antique stores and such.
 

·
Registered
Joined
·
4,596 Posts
I've heard of a CHESTERTON in Indiana, but never a CHESTERTOWN, and this is in Maryland. Charming little place.
 

·
Registered
Joined
·
186 Posts
Beautiful pics. Haven't been down the Eastern shore in many years. I did go down somewhere in the Chestertown vicinity, maybe past it, to go crabbing one time a number of years ago. The only drawback was leaving from Newark, Del by 3 AM to get down there before the crack of dawn.:scouserd:

Some little inlet off the Chesapeake Bay. Caught 3 bushels of crabs, had a few drinks on the way back, also stopped to get the crabs steamed and bay-seasoned. Good times.

I can recall passing by some quaint old towns on that sojourn though. I think Chestertown may have been one of those towns we passed. Other than the occasional small town, it's a very rural area.
 

·
Banned
Joined
·
1,098 Posts
Great pics, Matt :cheers:
Gotta love this quaint, colonial coastal town:)
Kinda reminds me of the NC Outer Banks a little bit.

Again, great pics!
 
1 - 11 of 11 Posts
Top