Defined by 600 miles of coastline, Talbot County’s modern seafaring lineage hails back to 1694. Is was then that Talbot County’s first town, Oxford was mandated by Maryland legislation to become the Eastern Shore’s first port-of-entry. The town gained significant prominence as a result and remained a booming port of call for vessels from all over the world for over 75 years.
After Oxford’s port-of-entry was established, St. Michaels developed into a center of shipbuilding. The swift, sharp-hulled sailing craft, later known as the “Baltimore Clipper,” was crafted there and later became famous in the War of 1812. The War of 1812 was in large part fought on the Chesapeake Bay, with St. Michaels being attacked by British ships in August of 1813. Perry Benson, a veteran of the Revolutionary War, acted as Brigadier General, leading a citizen army which repulsed the British attack. Later, legends developed that lanterns hung in trees caused the British cannons to overshoot the town.
In the early 19th century, parcels of land on Tilghman Island were sold to oystermen wanting close proximity to prime local harvesting grounds. By the turn of the century, two thriving industries – steamboat service and seafood harvesting had been established. While steamboat service faded away, Tilghman Island’s seafood industry remains strong today.
Oxford, St. Michaels, and Tilghman Island are now popular vacation havens for those wishing to discover the beauty of the Chesapeake Bay lifestyle. Here are some ideas on how to experience it for yourself:
Where to Bunk
- Talbot County has a variety of inns, hotels, and vacation homes with waterfront views on deck just for you.
Get Nautical
- Ride the Oxford-Bellevue Ferry
Believed to be America’s oldest privately owned, continuously operating ferry, this route was officially established in 1683 to transport workers and goods across the Tred Avon River. Today, the beloved Oxford-Bellevue Ferry still shuttles cars, bikes, and passengers between the town of Oxford and the village of Bellevue. The ferry runs daily from mid-April through October, and weekends only through mid-November. - Tour the Chesapeake Bay Maritime Museum
Located on an 18-acre waterfront campus that includes numerous outdoor and indoor exhibitions, a museum store, and member’s marina, the CBMM is a short walk from the heart of historic St. Michaels. Scenic cruises, hands-on workshops and shipyard programs, as well as numerous annual festivals and special events help celebrate the area’s culture, boats, seafood, and history. Its fleet of historic watercraft is the largest in existence, and a working shipyard highlights the boatbuilding traditions of the Chesapeake Bay. Open year-round, with hours varying by season. - Visit the Tilghman Watermen’s Museum
This museum captures the distinctive culture and colorful heritage of Tilghman Island through collections of oral history, art, and artifacts. Hearing the island’s story gives insight into this close-knit community and gives a glimpse of what those who grew up here called “Paradise.” The Museum is open Saturday and Sunday, April through November, and by appointment. - Take a Patriot Cruise
The 1930s two-level steam ferry replica offers Miles River cruise tours giving insight into area history, historic homes, wildlife, and local watermen culture. The Patriot can also be rented for weddings and sometimes holds dinner cruises. - Get Out on the Water Yourself
There are so many ways to experience the maritime life on our corner of the Eastern Shore. Kayaking, paddleboarding, fishing, and more await. Here are some ideas to help get you started and how to make them happen. - Plenty of Other Adventures
Whether you want to make a splash into the Bay or stay on dry land, opportunities for adventure abound.
Where to Catch Dinner
- Get on Board for Some Waterfront Dining
Opportunities to gaze out at the Chesapeake Bay or its picturesque tributaries while savoring a delectable dish are numerous. From chef-run eateries and burger joints to bars and crab shacks, you’ll find just the right spot for you and your companions. - Prepare Your Own Bounty of the Sea
If you’re staying in a vacation rental and want to prepare your own seafood feast, head to one of these seafood markets for a wide selection of fish, shellfish, and crustaceans. Markets are also helpful with recipes, prepared foods, and steamed crabs.
