Written by Susan Elnicki Wade
June 2021
Knapps Narrows Drawbridge - destination - tilghman island - marinalife
Knapps Narrows Drawbridge

If you’re looking for a bucolic place to experience an authentic Chesapeake way of life, then plug Tilghman Island into your GPS and get ready to explore. Tucked away on Maryland’s Eastern Shore, this timeless treasure measures only three miles long and one mile wide, but it magically blends the past and present into one laidback getaway.

Archaeological evidence shows the island has been inhabited for nearly 13,000 years. Originally called Great Choptank Island, Matthew Tilghman inherited the land in 1707, and since then it has carried his name. Fertile soil fostered a vibrant agricultural business for centuries, but by the early 1900s, residents turned their attention to local crabs, oysters and fish for their livelihoods. Today at Dogwood Harbor, the Bay’s largest fleet of working skipjacks brings in fresh catch from the surrounding waters.

Landlubbers drive through Easton and St. Michaels to reach the Knapps Narrows Drawbridge that connects Tilghman Island to the jagged peninsula. Considered one of the busiest bridges in the country, Maryland’s only overhead counterweight bascule span lifts upward about 12,000 times a year to let boaters cruise through the passageway between the Choptank River and Chesapeake Bay.

Characters Bridge Restaurant - destination - tilghman island - marinalife
Characters Bridge Restaurant

On Tilghman, life evolves around the water. At the northern part of the island, marinas, restaurants, and charming inns and B&Bs create an energetic vibe along the shore. Driving down the tree-lined main street, you’ll find a few shops, general store, waterfront resort and historic churches. A new gated community now stands where seafood and tomatoes were processed years ago.

The must-see Tilghman Island Watermen’s Museum offers guided tours of its fascinating exhibits that chronicle the region’s history, culture and people. Its unique W-shaped architecture was designed to catch cooling breezes in the summer.

In the southern part of the island, which is a delightful place for riding bikes, nature takes center stage. It’s a bird watcher’s paradise, as geese, bald eagles, herons and waterfowl soar above plush, green foliage. Hopeful fishermen cast lines in the water near Black Walnut Point until an unforgettable sunset marks the end of another glorious day on the island.

Article and Photos by Susan Elnicki Wade.


Knapps Narrows Marina & Inn
Conveniently located near the bridge and restaurants, this marina has a full-service boatyard with a 35-ton lift, 1,000-foot floating dock, transient and seasonal slips, gas, showers, laundry and swimming pool. Its 20-room waterfront inn presents scenic views of the Bay.

Tilghman Island Marina & Rentals
Since 1999, this cozy marina has accommodated vessels up to 110 feet with amenities ranging from 30/50 amp electric and Wi-Fi to a swimming pool and a restaurant and inn next door. Slips are protected with 24/7 security, and sunsets are spectacular.

Wylder Hotel Tilghman Island
Newly renovated resort is now offering transient dockage for guests at the 50-room hotel and restaurant specializing in local seafood. Dog friendly and fun.


Tickler’s Crab Shack & Restaurant at Wylder Hotel
At this lovely 9.5-acre resort, guests can sip craft cocktails in Bar Mumbo, or choose between the renovated indoor dining room or the outdoor crab shack perched above the waves. Either spot is a winner with local crabs, oysters, garden fresh ingredients and a gorgeous waterfront property.

Dogwood Harbor Work Boats - destination - tilghman island - marinalife
Dogwood Harbor Work Boats

Tilghman Island Inn
Stroll around the grounds of this artfully restored inn, then settle in for an exceptional fine dining experience based on seasonal seafood that reflects the bounty of the Bay. The view from the patio presents animated waterfowl and a parade of boats passing by at sunset.

Characters Bridge Restaurant
Enjoy the always-entertaining show of the drawbridge rising up and down for a variety of vessels while you eat grilled steaks, local crabs and oysters, creamy soups, or hearty sandwiches.

Marker Five Restaurant & Tiki Bar
Also located at the foot of the bridge, this casual dining spot offers tiki cocktails under the stars along with well-prepared dishes from regional seafood to buttermilk fried chicken, pulled pork and lamb meatloaf.

Two If By Sea
On the island’s main street, breakfast and lunch are served, featuring French toast, omelets, quiche, waffles and other mouthwatering homestyle dishes.

Tilghman Island Country Store
This one-stop shop for provisions covers all the necessities for a day on the water: snacks, sodas, beer, wine, deli meats, take-out salads and sandwiches, and Smith Island cake by the slice.