Paddler on the Chester river with fall colored leaves on the trees in the background. Many reds and browns.


Chester River Water Trail

From the headwaters in Delaware to the river’s mouth between Kent Island and Rock Hall, the Chester River Water Trail encompasses more than 100 miles of waterways, a variety of ecosystems, and over 10,000 years of human history.

The navigable portion of the Chester River begins near the town of Millington, Maryland, where the river is heavily wooded, narrow, and winding.  After reaching the small town of Crumpton, the scenery transitions from woodlands to large waterfront farms. 

The lower Chester River near Rock Hall is over three miles wide and features excellent crabbing, fishing, sailing, boating, and scenic views.  Paddlers in canoes and kayaks can explore numerous tidal creeks entering the river which contain pristine wetland habitats and abundant wildlife.

Enter Your Location

Remember: safe use of rivers and any designated trails, at any time, is your responsibility! Trail maps are for informational and interpretive purposes only and are not meant for navigational purposes, nor do they take into account level of skills or ability required to navigate such trails. The Chesapeake Conservancy, National Park Service, and/or the individual trail associations assume no responsibility or liability for any injury or loss resulting directly or indirectly from the use of trails, maps or other printed or web-based materials.

Main image: Chris Cerino / Sultana Education Foundation


Hours vary, please visit or call the particular landing before your excursion.


Some applicable fees.

These fees vary, please visit or call the particular landing before your excursion.


  • Kayaking
  • Canoeing
  • Crabbing
  • Fishing
  • Sailing
  • Boating


The Chester River's public landings feature a wide range of facilities, ranging from substantial, well-constructed boat ramps suitable for the largest trailered boats, to simple dirt roads ending at the water.  
Please visit or scout out a particular landing in person before using it.

Trail History

During his exploration of the Chesapeake Bay in August 1608, Captain John Smith visited an American Indian community at the mouth of the Chester River, which he referred to as "Ozines."

This site was most likely located in the vicinity of present-day Rock Hall.

Smith did not travel up the Chester River's main stem, in part because the river offered little promise of providing the elusive "Northwest Passage" to the riches of Asia.

However, Smith did chart the river's mouth, Kent Island, and the forested interior of what would later become Kent and Queen Anne's counties.

Last updated: October 05, 2021