Courtesy Kent Manor Inn

The Kent Manor Inn, located on Kent Island, the largest island in the Chesapeake Bay and the third oldest permanent English settlement in the America, has a long, grand history.

This luxurious waterfront hotel is located on 220 acres that was originally part of a larger tract of land granted to Thomas Wetherall in 1651, 20 years after Kent Island’s founding by the surveyor and fur trader William Claiborne. Wetherall was eventually purchased by Dr. John Smyth and renamed Smithfield.

The still-existing tenant house, a private residence, may date back to the late 1700s.

Kent Manor Inn today consists of a large middle section with nearly matching wings on either side, the easternmost of which is the building’s original structure, circa 1820.  A large, prestigious home for its day, Smithfield featured a living room, dining room, a large kitchen, and a pantry on the first floor, four bedrooms on the second floor, and two large rooms, perhaps for servants, on the third. The property remained in the Smyth family, until Sarah Smyth Thompson, wife of Dr. Samuel T. Thompson, granted the estate to their son, Alexander Williamson Thompson (1816-1875) in 1843. The current center portion of the manor house, with its iconic eight-window cupola, was added by Alexander Thompson just prior to the Civil War.

The Thompson heirs sold the property to James Benjamin Bright in 1898. For a time, during the days of the fine Chesapeake Bay resort hotels (which lasted from late in the 19th century until around the time of the Second World War), Bright’s oldest son operated a summertime hotel here called The Brightsworth Inn.

There is still graffiti from this era on the walls leading up to the cupola.

Brightsworth Inn closed in 1911. The Bright family farmed the property until selling it to  John Reifsneider in 1917. Reifsneider maintained an agricultural operation until he sold to Theodore Elliot Tolson in 1922.  Tolson reopened the house again as a summer hotel, renaming it Kent Hall. After the death of Mr. Tolson in 1951, the farm was bought by T. Worth Jamison and called Pennyworth Farm.

By the 1970’s, the old mansion, once derided as Alexander’s (Thompson) Folly, by some locals, sat abandoned and neglected, a sad rundown version of what must have once been an active, beloved, and dignified homestead.

c. 1980 Courtesy Reggie Jones

Fred Williams, a successful Washington D.C. area land developer and construction entrepreneur, armed with vision and resources, purchased the property in 1986.

The general consensus was that Fred had bought a white elephant, and the only plausible thing to do with the old house was tear it down.

Instead Fred Williams built a brand new west wing, restored the existing structure to its former grandeur, and outfitted his Kent Manor Inn with modern restaurant and lodging facilities. Moving forward with focused deliberation, Fred was dedicated to maintaining the inn’s historical accuracy wherever possible – from the handwrought wooden staircases and Italian marble fireplaces to the graffiti on the cupola walls.

Before and after

Fred Williams eventually sold the Kent Manor Inn, and after changing hands a couple times, the property was purchased by Sunny and Jigna Patel in January 2017. The Patels modernized some, but like Fred Williams before them, tried to maintain the property’s historical legacy, as well as it’s connection to the land and the water of the Eastern Shore.

Always a popular wedding destination and business retreat, The Kent Manor Inn, with its 24 guest rooms (many featuring fireplaces, four post beds, and balconies) and proximity to Annapolis, Baltimore, Washington D.C., and Virginia, also provides a retreat for smaller, more personal romantic getaways