Great Oak Manor
10568 Cliff Road
Chestertown, Md.
410-778-5943
GreatOak.com

Standing in front of the great oak manor, I feel downright Lilliputian next to the grand Georgian manor house, a celebration of symmetry and all things highbrow. Turning the slick brass handle of the massive front door, I find myself in the main parlor, where a delicious dose of quiet and Charlie, a golden retriever puppy, welcome me. Not far behind him is my hostess, Cassandra Fedas, who owns the inn with her husband, John. “This is a place where people come to rejuvenate,” she says. “You can be as busy as you want to be—you can get into all kinds of sports or you can vegetate on the hammock by the water. It’s also a romantic place. Lots of people come for anniversaries. We used to give out champagne for every guest’s birthday, but we stopped when we realized we were handing out eight bottles every night.”

It’s neither my birthday nor an anniversary, but the idea of sipping a little bubbly in front of a fireplace makes me think the Great Oak Manor will suit me just fine.

THE INNKEEPERS After 17 years as a TWA flight attendant, Cassandra decided to turn in her wings for nerves of steel and open an inn. “About 20 years ago, John and I became really interested in the B&B lifestyle,” says Cassandra. “It was a natural for us. I was used to taking care of 300 people on a 747 going across the ocean, and John’s family worked in the restaurant
industry. But this was more interesting.” 

In 2002, they purchased Great Oak Manor, a 1938 Georgian-style, 15,000-square-foot house that had been open as a B&B since the late ‘40s. “I deal with the guests and the employees,” says Cassandra, a native of Catonsville. “John handles the accounting, weddings, corporate guests—and the landscaping. Like most B&B owners, we do everything ourselves.”

THE ROOMS Of the inn’s 12 rooms (most named for former owners of the house), there are two roomy suites (the Roese and the Sterling suites), seven have water views, and five boast working fireplaces. Each is decorated in a period theme, dressed with Williamsburg paint colors, replica antiques, and private baths. The couple’s private collection of oil paintings hangs throughout the inn.

SPECIAL TOUCHES/DIVERSIONS Cassandra and John keep a fleet of bikes and kayaks at the inn, where a petite indoor pool is open year-round. Sports fans can play 18 holes at the nearby Chester River Golf Club, sail on the Bay, or kayak on the Chester River. During fall, guests need not go any farther than the fields surrounding the inn to see thousands of migratory birds en route southward. (Don’t miss the bald eagle that makes a daily appearance in the sky above the inn’s back lawn.) Shoppers can kill a few hours in downtown Chestertown, just 10 minutes away, where restaurants, clothing boutiques, art galleries, and the Prince Theatre dot High and Cross streets. 

WHAT’S FOR BREAKFAST Cassandra serves as the inn’s head chef. Her morning menu includes fruit, homemade breads and pastries, yogurt, cereal, waffles, sausage, and crab quiche, her signature dish. “It’s a huge meal,” says Cassandra. “Most people don’t have room for lunch.”

ROMANCE FACTOR This is a sprawling country inn where kids aren’t allowed and cell phone reception is spotty, so use your imagination. 

COST $185 to $310. Throughout winter and early spring, guests can enjoy live jazz performances by Centreville musician Stefan Scaggiari, followed by a five-course dinner. Call for dates and rates.