Day 590 – August 17, 2023 – Rock Hall, MD to Chestertown, MD – Chestertown Marina

  • 16.7 miles
  • 2 hours 16 minutes
  • 7.4 mph average speed
  • 3-6 mph winds

The boat ran great on the beautiful cruise up the Chester River to Chestertown. We absolutely loved Chestertown and are so glad we decided to visit the town. Chestertown was established in 1706 and is situated on the most traveled highway between the North and the South during the Revolutionary period. George Washington made eight known visits here between 1756 and 1793. The historic downtown area is a short walk from the marina and is filled with historic buildings, shops and restaurants. Beautiful homes surround the downtown area including many from the 1700’s.

We had some wonderful meals at Play it Again Sam, Modern Stone Age Kitchen and The Retriever Bar and, of course, ice cream at Sugar Doodles Sweet Shop.

We enjoyed doing the self-guided walking tour of historic Chestertown and loved looking at the houses from the 1700’s and reading about their history. Of particular interest was the White Swan Tavern, built in 1733 as a residence, enlarged to become a tavern in the 1793 until it became a general store in the 1850’s. It was restored in 1978 during which time an archeological excavation yielded some 70,00 objects from around the site. The Tavern reopened as a Bed & Breakfast in 1981 after being restored to its 1795 appearance. We decided to walk in and see if we could have a look around and were greeted by the lovely proprietress who welcomed us and gave us a brief tour of some of the rooms which were absolutely stunning! We could definitely spend some time here, given the opportunity!

Later, we took the loaner tricycles out for a ride on the old railroad trail. As much as we have ridden bikes on our tip, Ellen had to practice riding the tricycle before we ventured our of the marina parking lot!

We also walked over to the Washington College campus, founded in 1782. This was the first college chartered after American independence and the 10th oldest college in the United States. George Washington granted use of his name to the college and served on the Board of Visitors and Governors and received an honorary degree of Doctor of Laws in 1789 once he became President and retired from the board.

Downtown Chestertown
Downtown Chestertown
Downtown Chestertown
Widehall, built in 1770
201 N. Water Street, built in 1780, currently for sale for $1.9 million
The Frisby House, built in 1770
The Wickes House, built in 1767 has 15 fireplaces
Buck-Bacchus House, built in 1735
The Nicholson House, built in 1788
The Geddes-Piper House, built in the 1780’s. The original kitchen is still in the basement.
The Courthouse, built in 1860, replacing the 1706 courthouse
Kent County Offices – erected in 1901 as the public school
Christ Methodist Church, built in 1887
White Swan Tavern, built in 1733, is said to have provided refreshment to General George Washington on one of his visits to Chestertown
Stam’s Hall, built in 1886
The Custom House, built in 1746, replaced the original Custom House which was an official Port of Entry of the original 13 colonies.
103 N. Water Street, built in 1796
The Watkins-Bryan House, built in 1740 is probably the oldest surviving house on Water Street
The River House, built in the 1780’s
The Perkins House, built in the late 1700’s
201 S. Water Street, built in 1857
Fountain Park was created by the Ladies Improvement Society, forerunner of the Chestertown Garden Club, The fountain, crowned by Hebe, goddess of Youth and Beauty and cupbearer to the Gods, was erected in 1899.
The Hynson-Ringgold House, built in 1735, has been the residence of the presidents of Washington College since 1944
Partial side-view of the Hynson- Ringgold House
White Swan Tavern Bed & Breakfast – Breakfast Room
White Swan Tavern Bed & Breakfast
White Swan Tavern Bed & Breakfast
White Swan Tavern Bed & Breakfast – Sterling Suite
White Swan Tavern Bed & Breakfast – Sterling Suite Sitting Room
White Swan Tavern Bed & Breakfast – John Lovegroove Kitchen Guestroom
Play in Again Sam’s where we ate lunch
Kevin on the loaner tricycle from the marina
Washington College, founded on 1782
Washington College Hill Dorms – Middle Hall, built in 1844, is the oldest existing building on the site of the original building which was destroyed by fire in 1844. By 1860, Middle Hall was joined by East and West Halls.

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