Chesapeake Bay
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[Anchorages] [Miscellaneous]
You could cruise the Chesapeake Bay for years and not see all the beautiful anchorages and towns.  The following places are some of the best places to cruise around the Annapolis area and middle Bay.
Beautiful Tred Avon river near Oxford - premier cruising grounds on the Chesapeake Bay




Eastern Shore Anchorages

Very beautiful especially in the Autumn with the colorful oak, dogwood and maple trees.  Fly-way for Canadian geese where marsh grasses and harvested cornfields draw thousands.  Hear their soft honking in the morning and evening.
  • Wye River 
Narrow river, but with good depth, surrounded by colonial plantations, with large oak trees over-hanging the edges.  This river is off of Eastern Bay, the entrance to which is by passing Bloody Point Lighthouse.  One of the best anchorages is Dividing Creek located on the eastern side of the Wye West River.
  • St. Michaels
Wonderful little town with cute shops, crab houses, restaurants, old lighthouse
  • Tred Avon River
Another beautiful, navigable river off of the Choptank River, south of Eastern Bay.  (See picture above.)
  • Oxford
Lovely colonial town on the Tred Avon River 
  • Chester River
This entrance to this river is north of the Chesapeake Bay Bridge.  Many beautiful anchorages

Western Shore Anchorages

  • Severn River
Many great places to anchor on both sides of the river as you travel up-river.
  • Whitehall Bay
Just opposite the Naval Academy by the radio towers.
  • South River
Very crowded on weekends, but there is a terrific anchorage on Harness Creek by Quiet Waters park, located on the north side of the river 
  • West River
Travel up the river to Galesville.  Wonderful little waterfront town with good restaurants and shops.
  • Magothy River
The entrance is north of the Bay Bridge.  Many good anchorages, but a really nice one is near the private Gibson Island.  This is a private community for the super-rich.  You must own property  to get on the island, so please do not go ashore uninvited.


More Information -  

Guide to Cruising the Chesapeake - Gunkholer's Guide, Shellenberger, William.  This is an excellent guide to all of the anchorages, bays and coves in the Chesapeake Bay.  This gentleman is a local and, along with his family and two dogs, has cruised the Chesapeake for more than 10 years on their sailboat, Draussen.


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