Newsletters  | Mobile

Maryland's Timeless Eastern Shore

The place to stay in Chestertown is the elegant old Imperial Hotel on High Street. If you prefer a bed-and-breakfast, try the White Swan Tavern (ask to stay in the original kitchen, which has a huge fireplace and a door leading to the garden), and don't miss high tea there. Uncle Robert and I dined at the Imperial Hotel, on corn-and-crab bisque so rich you hardly need anything else. Uncle Robert also attests to the rack of lamb, and I to the rockfish, a local variety that had been scarce for 30 years and has miraculously come back in force.

ST. MICHAELS, ONCE A ROUGH SAILORS' HANGOUT, is now quite a tourist spot, with restaurants serving mesclun salad and roasted goat cheese. The antiques stores are good, too; I almost left with a $400 pie safe. Instead, I made my way down to the superb Chesapeake Bay Maritime Museum and got embarrassingly teary-eyed with patriotism in front of the clipper-ship exhibit. Then I had a fabulous bowl of corn-and-crab chowder at the Bistro St. Michaels on Talbot Street.

By the time I reached the Black Walnut Point Inn, at the very tip of Tilghman Island, the sun was slipping into the bay like a fat, ripe tomato and fishermen were silhouetted against the sky. The inn occupies an old farmhouse with a working jukebox in the sunroom and rockers on the front porch, from which I watched an osprey carry a mouse across the water. Two Chesapeake Bay retrievers greet you at the front door, and there is fresh lemonade waiting in the refrigerator. I could imagine renting one of the inn's two cottages for a few days with friends, cooking fresh fish, and watching the sun rise on the Choptank and set on the bay.

That evening, back in St. Michaels at 208 Talbot, I ate roasted oysters—plump, jumbo beauties, with a hint of pistachio and bacon—and soft-shell crabs. Boring, I know, but it was my last night on the Eastern Shore, and they were perfectly cooked. A man with a ponytail was discussing Windows 95 with his girlfriend as my lemon tart and espresso arrived. I felt worlds from Ruke's on Smith Island.

I drove the 10 miles back to Black Walnut Point with my windows open to the sound of crickets, and took a walk under the walnut trees. The stars were out, the wind rustled the leaves, and I could hear the lap of the waves. I lay down on the grass and let the feel of the solid earth seep into my bones. Then, after looking around to make sure no one was about, I hugged a black walnut tree.

Seven Wonders of the Eastern Shore

  1. The crab cakes at Ruke's Seafood Deck. As fresh as you can get.
  2. The Black Walnut Point Inn, a farmhouse turned B&B at the tip of Tilghman Island. Unpretentious atmosphere, good sailing and kayaking advice, and a wildlife sanctuary at the back door.
  3. The 25,000-acre Blackwater National Wildlife Refuge (410/228-2677), for birding, canoeing, kayaking, crabbing, and fishing. This is migratory-waterfowl heaven.
  4. The Chesapeake Bay Maritime Museum (Mill St., St. Michaels; 410/745-2916). The place to soak up a little Eastern Shore history. See the only log-bottom bugeye in existence; crew on a skipjack during the annual May and September races on the Miles River.
  5. Chestertown's sea captains' manses along the Chester River. On the third Saturday in September, there's a candlelit tour of 16 dwellings in the historic district. For info, call 410/778-0416.
  6. The wild horses that roam free at Assateague Island National Seashore (410/641-3030) and nearby Chincoteague National Wildlife Refuge (757/336-6122), in Virginia. Keep an eye out for dolphins and gray seals offshore, where you too can ride the rollers.
  7. The roasted oysters and pan-fried soft-shell crabs at 208 Talbot. The intimate bar is perfect for a martini.


Sign Up

Connect With Travel + Leisure
  • Travel+Leisure
  • Tablet
  • Available devices

Already a subscriber?
Get FREE ACCESS to the digital edition