Guided Trip To Rock Hall Maryland

Departure: South River, Maryland – 10am
The trip begins on the South River, a beautiful tributary of the Chesapeake Bay, just south of Annapolis. As you depart, you’ll pass charming waterfront homes, marinas, and lush, tree-lined
shores. Keep an eye out for Thomas Point Shoal Lighthouse, a historic screw-pile lighthouse that sits just outside the mouth of the South River. It’s a fantastic photo opportunity and a classic
symbol of the Bay.

Crossing the Chesapeake Bay
As you head east across the Chesapeake Bay, you’ll enjoy wide-open water views, often dotted with sailboats, fishing vessels, and even the occasional pod of dolphins or ospreys hunting for fish. If the weather is clear, you’ll see the Chesapeake Bay Bridge stretching north, connecting Maryland’s western and eastern shores.

Wildlife Watching: The Bay is home to bald eagles, great blue herons, and rockfish
jumping from the water.

Fishing: This route crosses some excellent fishing spots for striped bass, bluefish, and crabs.

Approaching Eastern Bay and Kent Island
As you near Kent Island, you’ll pass by Bloody Point Bar Lighthouse, another historic lighthouse that marks the southern entrance to Eastern Bay. You can take a slight detour up Eastern Bay to visit St. Michaels, a charming waterfront town with excellent seafood restaurants, boutique shopping, and the Chesapeake Bay Maritime Museum.

If you continue past Kent Island, you’ll enter the Chester River, a calm and scenic waterway lined with peaceful creeks and inlets. This is a great spot for kayaking or anchoring for a swim.

Arrival in Rock Hall, Maryland (Arrival at 12:30pm Depart at 3:30pm)
Rock Hall, known as the "Pearl of the Chesapeake," is a picturesque, small fishing town with a relaxed, nautical charm. As you arrive, you’ll see Rock Hall’s harbor lined with sailboats and classic watermen’s boats.

Things to Do in Rock Hall:
Enjoy Fresh Seafood: Try Waterman’s Crab House for a classic Maryland crab feast with stunning waterfront views.

Visit the Rock Hall Beach: A small but beautiful beach perfect for a stroll or picnic.

Explore Eastern Neck National Wildlife Refuge: Just south of Rock Hall, this protected area offers hiking trails and excellent birdwatching.

Attend Local Festivals: Rock Hall hosts events like the Pirate & Wenches Fantasy Weekend and the FallFest.

Back to the South River at 6 PM
Final Thoughts

This boat trip is a perfect blend of adventure, nature, and relaxation. Whether you're looking for great seafood, scenic views, or a little history, this journey from South River to Rock Hall captures the very best of the Chesapeake Bay.

Cancel up to 2 days before the start time.