Chester is one of the longest of the deep, navigable rivers winding far into the upper Eastern Shore. Rich in history and scenic charm, it provides deepwater cruising 28 miles upstream to Chestertown. The river is well marked and easy to run under power but is also a fun and challenging sail for those who don’t mind a lot of tacking. Delmarva is agricultural in nature and many small coves nestle against fields or the lines of trees planted for wind block. Wide, winding, tree-canopied creeks fracture the mouth of river into a plethora of quiet anchorages.
Plan your boating trip on the Chester River, MD. Browse marinas, dockage, service yards, and navigation alerts.
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The Waterway Guide Team has gained extensive boating knowledge over the years, and now we are sharing all of the tips, skills and tools we’ve picked up along the way!