Travel: Quick Weekend Getaways: Chestertown, MD

Yes, we love claw-foot tubs, four-poster beds and four-course dinners. But equally important to any weekend-splurge-at-an-inn is getting the rhythm of your stay right. Pack in too much—or extend yourself too far, geographically speaking—and the tempo suffers. You lounge, but with an eye on the clock. Nap, but not quite, before your evening reservation. Our weekend sojourn to two inns on the Chesapeake’s Upper Bay did away with any such back-and-forth, proving an ideal, easily navigated 48 hours away.

We hit the rolling fields of the Bay area in under two hours, then found our way to the long drive leading up to our first inn, Great Oak Manor. The inn’s namesakes lined the way, harbingers of the grand old house at the apex of the circular gravel drive. Originally built in 1938 as a family residence, Georgian-style Great Oak has been in service as an inn on and off since 1946, when millionaire businessman Frank Russell made it a sportsmen’s club for his chums, who included Jack Kennedy and Robert Mitchum. His old gaming room is now a guest room, a masculine tribute to the man whose illegal high-stakes games got him locked up for a spell in the local jail.

The rest of the inn is a bit more formal, kept by innkeepers Cassandra and John Fedas, who came “up from Annapolis” to oversee its 12 rooms. From the grand entrance hall with its spiral staircase, to the carved bookcases in the library (grab a glass of port from the mahogany server on your way in), to the Oriental rugs and oil paintings in the music room, the inn isa ­meticulous yet welcoming place. Breakfast
is served in a formal dining room, or, on the day we visited, in the large glass atrium the Fedases added after buying the property in 2002.

The second-floor rooms with water views are especially pretty: Our Marmaduke suite—with tasteful floral wallpaper, wainscoting and swags—offered a working fireplace, comfortable reading chairs, a marble-topped dresser with a tray of midnight snacks, and binoculars with which to watch the geese on the water. In fact, some of the inn’s biggest draws are outside. Its back lawn slopes down to a screened gazebo and a row of Adirondack chairs overlooking a small beach. Guests can also use the pool, tennis courts and golf course at the nearby marina club for free.

If you leave the compound, there’s antiquing a short drive away in historic Chestertown. For rustic and reasonably priced farm tables made from recycled barn boards, hit Galena, a postage-stamp-size town nearby. (Inquire about the made-to-order tables at the Galena Antiques Center, 410-648-5781.) In Chestertown, be sure to walk toward the Bay and the historic homes that line Queen and Water streets. Also stop in for tea ($5 buys a spread of cider, tea, scones, pastries and more) at the White Swan Tavern, a bed-and-breakfast dating from 1733. While there, ask to see the John Lovegrove Kitchen Room, the residence and workplace of an 18th-­century shoemaker that was moved to adjoin the building.

The Eastern Neck Wildlife Refuge, on a peninsula reached by a straight shot south on Route 20 (about 25 minutes from the Great Oak), also makes a fine half-day trip. A haven for migrating and wintering waterfowl, the Fish & Wildlife Service refuge offers easy one-and-a-half-mile-long “hiking light” loops. For dinner, we hit a local favorite, the year-old BYOB Kettledrum, with hearty, comforting prix-fixe fare. (The theme of this night was Thai; the beef curry with brussels sprouts was better than it may sound.) We ventured all the way across the street on night two to the casual, quietly refined Blue Heron. Our best dish was the juicy, bread-crumb-free crabcakes; a close second were the local bay oysters.

We spent our second night at the Brampton Inn. Like the Great Oak, it sports true curb appeal—three stories of antebellum charm, with paired brackets running under the cornice on all sides, and a glass belvedere at the top. The owners, Michael and Danielle Hanscom, recently built a three-sided porch to closely resemble the original, then added ceiling fans and wicker seating to create a comfortable afternoon hangout. Inside, wide pine floors, foot-high walnut baseboards and a perfectly preserved walnut balustrade belie the house’s past, which includes stints as agricultural and meat storage.

The Hanscoms make an art of service; Michael greets guests as briskly as a butler, and asks if you might enjoy some tea in the dining room while he loads up your room’s fireplace with wood. After tea, we headed to the Blue Room for a little reading in the wingback chairs and a nap in the four-poster canopy bed, so tall that I needed the step stool to climb in. Best of all are the baths: Ours had a multi-directional shower, spa-like mosaic tile, and sleek fixtures. The Garden Cottage—a renovated horse barn—has double-wide Jacuzzi tubs in each of its two large suites, plus private brick patios; in a fenced garden in front of the cottages, the Hanscoms grow strawberries, rhubarb and flowers.

Breakfast at Brampton went far beyond sensible eating: We tried juices, fruits, muffins, tomato-and-goat-cheese omelet, sage sausage, and everything else posted on the day’s menu outside the dining room. The only drawback? The lavish meal signaled the impending 11 a.m. checkout.

Great Oak Manor, 10568 Cliff Road, 410-778-5943; Rooms from $155 to $225 through April 15th, $160 to $240 April through November.

The Brampton Inn, 25227 Chestertown Road, 410-778-1860; Rooms from $195 to $295.

The Kettledrum, 117 Cross Street; 410-810-1497. Dinner for two, about $70. BYOB.

The Blue Heron, 236 Cannon Street; 410-778-0188. Dinner for two, about $85 with wine.

The White Swan Tavern, 231 High Street; 410-778-2300.

Eastern Neck Wildlife Refuge has hiking and birdwatching. 1730 Eastern Neck Road, Rock Hall, Maryland, 410-639-7056; Free.

Travel Time: 2:00