Chester River, MD

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.

Purchase A Printed Chesapeake Bay Guidebook

Marinas, Dockage, Service & Navigation

Plan your boating trip on the Chester River, MD. Browse marinas, dockage, service yards, and navigation alerts.

View More Information to Plan Your Boating Trip In The Explorer.

Find More Boat Trip Planning Tools for Chester River, MD

Fuel

Marinas

Services

Anchorages

Free Docks

Alerts

Bridges

Locks

Boating Destinations near the Chester River, MD

Hyatt Regency Chesapeake Bay, MD

Chestertown, MD

Kent Narrows, MD

Galesville, MD

Chesapeake Beach, MD

Chesapeake City, MD

Oxford, MD

St. Michaels, MD

Eastport, MD

Edgewater, MD

Annapolis, MD

Havre de Grace, MD

Delaware City, DE

Georgetown, MD

Hyatt Regency Chesapeake Bay, MD

Oxford, MD

St. Michaels, MD

Eastport, MD

Galesville, MD

Annapolis, MD

Georgetown, MD

Chestertown, MD

Chesapeake Beach, MD

Rock Hall, MD

Edgewater, MD

Chesapeake City, MD

Delaware City, DE

Kent Narrows, MD

Learn More About This Destination

View This Boating Destination In Our Explorer

What's Nearby

Hyatt Regency Chesapeake Bay, MD

Chestertown, MD

Rock Hall, MD

Kent Narrows, MD

Eastport, MD

Annapolis, MD

St. Michaels, MD

Havre de Grace, MD

Chesapeake City, MD

Oxford, MD

Cambridge, MD

Georgetown, MD

Edgewater, MD

Galesville, MD

Delaware City, DE

Chesapeake Beach, MD

Rock Hall Harbor, MD

Swan Creek, MD

Worton Creek, MD

Sassafras River, MD

Kent Narrows

Severn River (Annapolis Harbor), MD

Susquehanna River, MD

North East River

Rhode River, MD

The Chesapeake & Delaware (C&D) Canal, DE/MD

Take Us Aboard

No Matter Where You Go

Purchase a Guide

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!

Download Our App

The Waterway Guide App makes it easy to leave reviews, use our Explorer, and view Waterway Guide materials, all on the go!

*In-App Purchases Available

Chester River, MD

Chester River, MD

Marinas, Dockage, Service & Navigation

Boating Destinations near the Chester River, MD

Apple Sign-In

Newsletter Sign-Up