Oct. 5, 2025 Historic Chestertown, MD

 Sun-Mon  Oct. 5-6, 2025  Lankford Bay Marina to Chestertown, MD  18 miles and 2.5 hours

While in Chestertown on Saturday for the farmers market, I took a stroll down to the marina and talked with the dockmaster.   Arranged for a slip on Sunday and Monday.  Just need to wait for some of the touring yacht club boats to leave.  So, no hurry to depart Lankford Bay Marina until about 10 for the 2-hour cruise up the river.  Another fine day to be out boating.   We head down Lankford Bay then take a sharp turn to port and begin the cruise north to Chestertown.   Wonderful river cruising although we're hitting it with a falling tide, so we're against the current which is slowing us down slightly.  Gives us a little extra time to enjoy the natural scenery, farmland and a few massive estates. 

This estate home on a peninsula of land caught our attention. Even more impressive
was the satellite view showing the guest houses, barns, gardens, pool, tennis courts, etc.

We get the prime spot on the outboard T-head on the new floating docks at Chestertown.  Our timing is perfect as several yacht club boats leave just as we arrive.  We spend Sunday afternoon just walking around town.  Much of it is in a designated historic district.  Chestertown was one of six designated royal ports in Maryland which led to its early development.  Trade and shipbuilding made the town prosperous. Wealthy merchants, shipbuilders, sea captains, lawyers and politicians built stately homes.  Today it has a population of just under 6,000 and remains a relatively small town despite being the county seat. It has the second highest number of 18th and early 19th century houses in the state - surpassed only by Annapolis.  The town was never involved in any direct battles or pillaging during the Revolutionary or Civil Wars which helped so many of the town's historic buildings survive.  Most impressive is that so many continue to be beautifully maintained.

Originally constructed in 1735, this impressive house is now owned
 and maintained by Washington College and used as the President's residence

The old Customs House dating to 1746.  Embellished with
Flemish bond brickwork with glazed headers. 

Many residential street sidewalks are brick.
 A bit uneven at times, but scenic.

High Street downtown is active with restaurants, galleries, boutique hotels, etc.

This circa 1796 house was expanded over time as wealth and style changed. 
 The 3rd floor with it's heavy cornice work, the front porch, and the
Queen Anne 2 story side windows were added later giving it a mixture of styles.

The 2nd floor window above the entry with its sidelights
 caught my eye for its great symmetry

The town squares centerpiece is this 1899 fountain 

Very Italianate style house on the waterfront. 
Built in 1857 making it one of the "newer" old houses. 

One of the surprises during our visit was Earthgrains Bakery Shop.   We stood in line on Saturday for twenty minutes waiting our turn for coffee and a pastry.  Returned Tuesday before our departure to load up on pastry, scones, and a baguette.  Signature item is their sunburst pastry.  Basically, a croissant, covered in cinnamon sugar and then baked in a muffin tin. Delish!!

Journey for Oct. 5, 2025