Play your cards right for romantic getaway


I dropped my bags in the most notorious room at Great Oak Manor, a bed and breakfast near Chestertown on the Eastern Shore.

The Russell Room is named for Frank Russell, the flamboyant former owner who in the late 1940s turned the property into a luxury lodge complete with four-star restaurant, golf course, hunting, horseback riding and plenty of gambling.

In the 1950s, Great Oak Manor was a retreat for high rollers and jet-setters -- corporate types, politicians and celebrities such as Arthur Godfrey, Guy Lombardo and Robert Mitchum.

The Russell Room in those days was filled with craps and roulette tables, and high-stakes poker players. Slot machines lined the hallways. The fact that such activity was illegal apparently didn't bother Russell, even after a raid in the early 1950s landed him in the county jail for 30 days.

Today, Great Oak Manor is a far cry from its rollicking past. Now, guests at the B&B; near the Chesapeake Bay are seeking a romantic getaway or peace and quiet, not an all-night card game.

The B&B; can accommodate corporate meetings and group retreats as well as weddings, but many couples come here for a simple romantic getaway.

American Historic Inns, which for the past five years has named B&Bs; and inns around the country as being ideal for couples in love, this year cited the Great Oak Manor as one of the 10 most romantic inns in the United States.

Deborah Sakach, who publishes the organization's rankings and guidebooks, says readers offered glowing comments about Great Oak Manor, and she had stayed there herself in the past.

The B&B;'s current owners, Don and Dianne Cantor, bought the house in 1993. By that time, Frank Russell, along with three other owners, had come and gone. Desperate for cash in the late 1960s, Russell sold off parcels of the 1,100-acre estate, and even chopped down old black walnut trees to sell the wood. In 1972 he sold the 25-room house.

The property now covers 12 acres at the mouth of Fairlee Creek, which, thanks to years of erosion, is wide enough to look like a peaceful cove.

The three-story brick mansion makes quite an impression as you approach on the long gravel driveway. In the foyer, there is a wide spiral staircase leading to 11 guest rooms. On the ground floor, guests can lounge in the music room or relax in the library with a glass of sherry in front of the fireplace.

The house has a "tranquil feeling," Dianne says, "like a grandmother is greeting you when you arrive. The very first afternoon we saw [the house] we had that feeling, and we put in an offer on it that day."

Homework pays off

Don and Dianne Cantor moved in on Valentine's Day seven years ago, and as they rehabbed the house during the next many months, they began to take in weekend guests.

In those days, they were learning how to run a bed and breakfast, which wasn't easy because before buying the place neither of them had ever even stayed in one. They worked with a consultant, studied how other successful B&Bs; around the country operated, and did their homework.

The hard work has paid off. The B&B; is popular, and Dianne notes that "we're already being approached with weddings for 2002."

The Cantors furnished Great Oak Manor with a mix of styles, and made sure everything came from the Chestertown area.

"I wanted to have the feel of a house in this area," Dianne says. "It's not a city house, it's a country house."

Many little touches make the B&B; comfortable, including fireplaces in five of the guest rooms. But perhaps the most appealing thing about Great Oak Manor is that it offers privacy.

It's easy to spend time in and around the house without running into other guests, and Dianne says guests can take breakfast back to their room or escape to the solarium if they prefer to eat by themselves.

"If you see a book you like in here," Don says in the library while giving guests a tour of the house, "take it on up to your room with you. Help yourself to hot cider, tea, coffee or soft drinks."

When they began operating the B&B;, the Cantors named the rooms after owners of the house. Hence, the Russell Room. Later, they began naming rooms according to the area's history.

There is the Marmaduke Room, named not for the cartoon Great Dane but for the area's first land grantee from Lord Baltimore. The Caulk Room is named after a nearby field on which patriots battled the British in the War of 1812. There is also the Wickes Room, named after Capt. Lambert Wickes, the first U.S. Naval officer commissioned by Congress in 1776 to carry the U.S. flag in foreign waters.

Chestertown charm

Chestertown, on the Chester River, is a charming Eastern Shore community with wide brick sidewalks and a comfortable square. On Saturdays until noon, you can buy fresh produce, bread and flowers from the many farmers who set up stands along the border of the square.

Nearby is Washington College, the 10th-oldest liberal arts college in the country, founded in 1782.

A few miles down the road from the Great Oak Manor you can see the spot where Captain Wickes' grandfather once had a fine house.

But the real treat of that trek is that the property is at the tip of the Eastern Neck National Wildlife Refuge. The refuge is a haven for more than 200 species of animals, winged and hoofed, and if you come in the spring or fall there are numerous migratory birds that pass by. Walking trails and observation towers lead the casual or serious birder away from the main road and into the thicket where the action is.

Eastern Neck is seven miles from Rock Hall, a small waterfront town with a marina, a few shops and restaurants and plenty of charm.

The Bay Bridge now keeps most motorists far to the south when they cross the Chesapeake Bay, but that has kept this charming hamlet from being overdeveloped. Stop in at one of the marina restaurants for the fresh catch of the day.

Back at Great Oak Manor, the Cantors talk about how they had to divide the responsibilities for running the B&B; between them to keep things running smoothly.

Don's background is in corporate affairs, so he arranges the meetings and business conferences, while Dianne tends to the wedding clients. And she takes care of most of the cooking chores.

"We've been married 35 years," Dianne says, "and working together for the last seven. I'd much rather him be the bookkeeper than me. I respect his business sense," she adds, "but I make a much better muffin than he does."


Great Oak Manor, 10568 Cliff Road, Chestertown, Md. 21620

* Phone: 410-778-5943 or 800-504-3098

* Online:

Getting there: From the Bay Bridge, follow Route 50 to Route 301 north. Take Route 213 north through Chestertown. Turn left at the light on Morgnec Road (Route 291). At the dead end, turn right on Route 20 and then immediately right again on Route 514. Continue straight through the stop sign at Route 298 and then bear left after 1.8 miles onto Great Oak Landing Road. Great Oak Manor is at the end of the road.

Room rates run from $95 to $175, or $85 to $160 for groups. Great Oak Manor is closed for seven weeks in the winter (most of December and February).


* The Blue Plate: Casual fare -- mostly salads, sandwiches and burgers -- with good crab cake sandwiches. The restaurant is on the main square in Chestertown and features artwork on the walls by local artists. 323 High St., 410-810-1433.

* Play It Again Sam: A cute coffee shop recommended by Chestertown residents. You can sit outside and enjoy your dessert. 108 South Cross St., Chestertown; 410-778-2688.

* Waterman's Crab House Restaurant & Dock Bar: Good for crabs and ribs. It's on the water in Rock Hall and has indoor seating and a large patio area. It also has a gift shop. Sharp Street Wharf, 410-639-2261.

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