By: Tom Adkinson

Memorable hotel rooms have stories to tell. My room at Great Oak Manor on Maryland’s Eastern Shore once was a gambling den. Cool, very cool.

A previous owner, several decades before the place became the romantic bed and breakfast it is today, played fast and loose with the social conventions of kinder and gentler times. He had no qualms offering a little excitement to celebrity guests, reportedly including actor Robert Mitchum, who visited this off-the-beaten-track piece of the Free State.

The Eastern Shore still is a bit isolated, but the Bay Bridge linking the Annapolis area with Kent Island and the rest of the region at least makes it a straight shot from the “mainland.”

Most visitors cross the bridge, and then zoom south down U.S. 50, headed for the crush of Ocean City and its beachfront.

Others, however, angle north for a quieter corner of the Eastern Shore. I took the northern road and found quiet, good food, quaint towns, my accommodations in a former casino, plus a most unusual swim.

Great Oak Manor is an impressive three-level, red-brick structure at the end of a cedar-lined drive. It looks like an 18th Century English country estate and is about eight miles from Chestertown, a river town whose first courthouse was built in 1697. Chestertown´s has a civic aura that seems to say “we´re quite comfortable with our isolation, history and a cocktail at sunset.”

Innkeepers and owners Cassandra and John Fedas personify that attitude. They show off the shaded back side of the property that leads to a private beach on Chesapeake Bay, invite guests to explore their 850-volume library and point out the globe in the music room.
The globe opens along the equator to reveal decanters of sherry and port. The invitation is implicit.

Names of the manor´s rooms have local connections. My room, the Russell Room, was a gigantic space with a king bed, wing-back chairs, a giant armoire, towering ceilings, waterfowl and hunting dog artwork and pine paneling. It was easy to imagine felt-topped tables and a couple of slot machines overseen by one-time owner Frank Russell.

Other rooms had names of a nearby battlefield from the War of 1812, a colonial land grant recipient and the first naval officer commissioned by the Continental Congress. There are 11 rooms and an equal number of tales.

The manor is strategically located for excursions to Chestertown (for Washington College, founded 1782; the Sultana, a replica of a 1768 British schooner; restaurants such as the Cross Fire Inn and Brooks Tavern) and to Rock Hall (for a photogenic marina, a few blocks of shops and crabs, crabs and more crabs at the Waterman´s Restaurant).

And what about that memorable swim? It was in one of those newfangled “endless lap pools” in a conservatory addition to the manor. There´s nothing like a relaxing, indoor swim that offers a view across acres of green lawn and the golden sun as it sets over the Chesapeake Bay.

Full details about the Great Oak Manor are at www.greatoak.com. Information about Chestertown and surrounding Kent County is at www.kentcounty.com.

This article was featured in “Where to go Next” on June 19th, 2009.