A Maritime Themed Tour of Talbot County

Defined by 600 miles of coastline, Talbot County’s seafaring lineage hails back to when Oxford, its first town, and one of Maryland’s oldest, was mandated in 1694 by Maryland legislation to become the first and only port-of-entry on the Eastern Shore. The town gained significant prominence in colonial days and remained a booming port of call for vessels from all over the world for over 75 years.

St. Michaels was the county’s early shipbuilding center and created the swift, sharp-hulled sailing craft later known as the “Baltimore Clipper,” famous in the War of 1812. Much of that war was 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 had been established, with a crabbing and fishing industry still thriving 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

The Robert Morris Inn in Oxford

Robert Morris Inn building front.

This historic inn, built in 1710, was the home of Founding Father Robert Morris Jr. who gained fame as the “financier of the Revolution.” Located in Maryland’s earliest seaport town, it now offers a unique inn experience, complete with a tavern-style restaurant.

The Inn at Perry Cabin

Sailboat at the Inn at Perry Cabin in Talbot County, Maryland.

Seated on the west side of Maryland’s Eastern Shore, the estate was designed and built by Samuel Hambleton in 1816. A War of 1812 Navy veteran and aide-de-camp to Commodore Oliver Hazard Perry, the home was built to resemble the Commodore’s cabin (‘Perry Cabin’) on the flagship U.S.S. Niagara. Hambleton also named the adjoining farmland Navy Point, which today contains the Chesapeake Bay Maritime Museum. Today, the inn sits on 26 acres along the Miles River and offers a host of exclusive amenities.  

Hambleton Inn Bed & Breakfast

The home was built by shipbuilder Edward Willey, and is where he and his family of eight children resided in the mid-1800s. It was adjacent to Willey’s boatyard, currently still operating as Higgins Boat Yard. Edward Willey was a renowned shipbuilder in his time and there is evidence of his skills in the construction of the home. Today, it is now a Victorian combination bed and breakfast with modern amenities and easy access to the shopping, eateries, and attractions of St. Michaels.

Other Fish in the Sea

Talbot County has a variety of inns, hotels, and vacation homes on deck just for you.

Get Nautical

Ride the Oxford-Bellevue Ferry

Oxford-Bellevue Ferry out of Oxford, Maryland.

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

The Chesapeake Bay Maritime Museum in St. Michaels, Maryland, is tailor-made for family fun.

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, and 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

The Tilghman Watermen's Museum in Talbot County, Maryland.

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

Patriot Cruise Ship

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.

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The sounds of an old-fashioned Town Crier will resonate at the Talbot County Courthouse on Friday, May 24 as the community takes a step back in time to celebrate the 250th anniversary of the Talbot Resolves. The free public event kicks off at noon, rain or shine, with light refreshments served.

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