Chesapeake Bay

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

Anchorages

Location	Comments
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.

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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[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.

Anchorages

Eastern Shore Anchorages

Western Shore Anchorages

Miscellaneous