Eastern Bay is a significant, open-water bay off the main Chesapeake Bay in Maryland, bordered by Kent Island to the north and the mainland to the south and west. It is a tidal saltwater feature with a reputation for becoming rough and choppy when winds pick up, as it offers a long fetch for waves to build. Paddlers should be prepared for open water conditions and plan trips carefully around wind forecasts. The bay provides access to several sheltered creeks and rivers, including the Wye East River, Miles River, and Warehouse Creek, which offer protected paddling and anchorages away from the main bay's exposure.

Several public launch points provide access to Eastern Bay and its tributaries. On the western shore, Bayshore Road offers a beginner-friendly bank access with sheltered, tidal conditions, though parking is limited to two spaces and a fee is required. The Matapeake State Park boat ramp on Kent Island provides a well-equipped launch with a large parking lot, restrooms, and a pier for a fee, suitable for accessing the more exposed waters of the bay. For access to the quieter northern reaches and the Chester River, a carry-in launch exists under the Route 50 bridge at Kent Narrows, though paddlers are warned of significant currents in the narrows themselves. Other county ramps on Kent Island, such as those on Goodhands Creek, Thompson Creek, and Crab Alley, require permits and provide entry to a network of marshes and creeks on the Eastern Bay side.

Tidal currents are a primary consideration, especially around the constricted Kent Narrows, where currents can be strong and hazardous to paddle against. Paddlers should consult tide charts and plan crossings or narrow passages accordingly. The bay experiences moderate to heavy powerboat and sailing traffic, particularly near the mouths of rivers and popular destinations like St. Michaels. Wildlife includes opportunities to see dolphins, notably near Kent Narrows. The best paddling seasons are generally from spring through fall, with mornings often providing the lightest winds for stand-up paddleboarding. Water trails and maps are available for the area, outlining routes ranging from short protected loops to longer cruises exploring the many secluded coves and historic waterfront estates.