Colonial style

Colonial style

This was my view recently as I reconnected with the girlfriends of my youth on the banks of the Chester River in historic Chestertown, Maryland.  I would typically save the sunset photo for the end of my post but decided to start here instead.  It was a weekend of reminiscing, laughing like school girls, and enjoying the discovery of an area that was completely off my radar until my friend, Amy Ennis and her husband moved there a few years ago.  Here’s a view of the river from the beautiful country club not far from Amy’s home.

This river sees a lot of action, from regattas to rowing and sailing by student athletes at Washington College, and one of the largest annual Tall Ship gatherings on the East Coast in November.

This gorgeous schooner named Sultana is used by the city for taking school children out as part of an educational experience for kids on the Chesapeake Bay. Lucky kids!

Besides all the waterfront activities, there’s the rich colonial history in Chestertown, which was founded in 1706.

It is a gorgeous walkable downtown with so many architecturally noteworthy homes.


Whether it was the aged brick or interesting architectural details like the brackets on the porch above,  it was so interesting to see these homes, many of which have great stories. I’ll give you a bit of history on several I thought you might find interesting.  These are on the walking tour in case you decide to visit Chestertown yourself some day. My friend Amy took the following pictures and was distressed that it was a cloudy day but that doesn’t take away from how fantastic they are to study.

First up,  Widehall on North Water Street that was built in 1770 by a merchant and shipbuilder that was thought to be Kent County’s wealthiest citizen at that time, and quite influential.

Thomas Smythe was a member of the local Committee of Correspondence of 1774. He was also head of Maryland’s Revolutionary Provisional Government from 1774 until the State’s first Constitution was framed in 1776.  The mansion is a statement of the symmetry and proportion of Georgian architecture,  notable for its half-columned Doric portal and the fine frames around the 12 over 12 windows that are capped by keystone flat arches.

Next, is the River House, also on North Water Street.  This was also owned by Thomas Smythe.

This elegant mansion is a National Register Landmark, circa 1780’s.  It was built in the Federal style using Flemish bond brick on the street side and American bond on the other sides. Houses one room deep with no windows on the sides except in the attic were characteristic of Philadelphia town houses.

The Frisby House on North Water Street was built in 1770 and for generations was the only dwelling on the town side of this waterfront block. (By the way, my friend Amy wishes she could have taken pictures of the water side or back side of these gorgeous homes, but she would have had to be in a boat!!!)

It’s notable for its wide chimneys with interesting cap detail, all header bonding, and curvilinear window arches.

And I also wanted you to see the Wickes House on High Street.  It’s a Georgian-style house, now owned by a well known business executive.

The Wickes family was very civically involved in the town.  The house has five bays, a gabled roof and dormers and get this; fifteen fireplaces!!!!!!  The four-square Flemish brick construction fits the generation of the building just prior to the Revolution. It was built in 1767 for the Wallis family.  I just can’t imagine the maintenance that these lovely homes require!

Here are some other homes I took pictures of but I don’t know their history. I just thought they were interesting and  have great pops of color.


In the downtowbn area you’ll find Stam’s Hall which is in the Second Empire or Beaux Arts style. This structure was built in 1886 to house druggist and merchant Colin Stam’s flourishing business on the main floor with spaces for entertaining on the upper floors.

The people of Chestertown contributed one thousand dollars to pay for a bell in the tower which still tolls the hours!!!

I also enjoyed seeing the side street that’s known as Lawyer’s Row.

And what would a small colonial town be without a cool historic tavern?!?  Here it is.   The White Swan Tavern which is said to have provided refreshment to General George Washington on one of his visits to Chestertown.

It was built in 1733 as a residence by Joseph Nicholson.  Later in the century it was enlarged into a tavern, then later a general store.  In 1981 the Tavern reopened as a Bed & Breakfast and restored to its 1795 appearance.


The town’s gorgeous fountain features Hebe, the goddess of youth.

As you might expect, today there are some trendy additions that include a very cool coffee shop we visited, called Evergrain Coffee. But its front window features many old telephones.

And I must show you the exquisite wood art on the wall made by renowned wood artist, Vicco von Voss.

Vicco’s work is also shown at the nearby Maissoniart Gallery where you’ll find meticulously curated artwork.

Vicco von Voss is a master at creating beautiful sculptures, shelving, and furniture out of wood and has been featured in the New York Times.  Here are a few other pieces of art we enjoyed in the gallery.

Artist Greg Mort Origami watercolor

Chestertown is rich in the arts.  We also wandered into the Riverarts’ popular Clay Studio that provides equipment and workspace for potters and has classes for all levels of students.

The shop dog, Sweetie, greeted us ever so tentatively.   If I had a shop, I would have to have my dog there too.

I’m going to think about this trip for a long time because being with these old friends isn’t something that happens very often.  The sightseeing was wonderful but the best part was being together and remembering our shared experiences.  We just made more memories to last ’til our next reunion at another stylish retreat.


      Thank you for following Stylish Retreats.  And a huge thank you to our tour guide, host and dear friend, the other Amy in our group,  Amy Ennis.  We had the best time!!!  I hope you all have friends to reminisce with like I’m fortunate to have in my life.  




























  • Bell Newton
    Posted at 07:30h, 03 April Reply

    Such a fun post!

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