Route 33 South takes you to the quintessential historic American waterfront village of Tilghman Island. This 20-minute drive is an experience unto itself. Just off the beaten path, Tilghman Island is nestled between the Chesapeake Bay and the Choptank River. Boaters know it well, as Knapps Narrows is a popular shortcut to Oxford.
Immerse Yourself in Maritime History
As you cross the Tilghman Island Drawbridge, drive by the Tilghman’s Pride Mural, located at 6123 Tilghman Island Road. The Tilghman Watermen’s Museum is housed in a historic W house — shaped like the letter — formerly belonging to a waterman. It focuses on the culture of those who have carved out a living on the Chesapeake Bay, reflecting their stories through videos, artifacts, and a significant collection of model boats.
Memorable Views
Explore the island, as it’s only 3 miles long and 1 mile across at its widest point. At Dogwood Harbor, a cove near the center of town, you can watch local watermen haul in their catch and get an up-close view of historic skipjacks, iconic 19th century sailboats designed for oyster dredging. On the main street, you’ll find the Tilghman Island Country Store, a down-home place known for its desserts. Pick one and drive to the end of the island, where you’ll find Black Walnut Point Natural Resources Management Area and a spectacular view of the open waters of the Chesapeake Bay.
Get on the Water
Rent jet skis, pontoons, sailboats, and kayaks, or pick up crabbing equipment should you be so inspired. Fishing charters, led by experienced captains who know how to chase the Bay’s bounty, will take you directly on the Chesapeake Bay.
Knapps Narrows separates Tilghman Island from the mainland, creating a busy channel that gives boaters and kayakers access to the Chesapeake Bay.
Fresh Seafood
For dinner, nothing gets you closer to fresh Chesapeake Bay seafood than Tilghman Island. From a waterfront tiki bar to classic Eastern Shore fare, including Maryland blue crabs, oysters and rockfish, Tilghman Island has a variety of restaurants. For breakfast, a lively, unpretentious spot where you can rub elbows with locals offers a variety of hearty skillets.
Stay on the Water
A retro cool hotel that is all about fun with nightly bonfires, cornhole, a wood-fired sauna, cocktail classes, and a lively crab deck is waiting to welcome you. Capture both sunrise and sunset while swaying in a hammock from within a serene oasis on a point overlooking the Chesapeake Bay and Choptank River. Enjoy an elegant boutique hotel set on the waterfront where the chef/ owner taps local ingredients for his menu.
