See the Bay: Sailing to Five Eastern Shore Rivers

Cruisers love sailing to these five Eastern Shore rivers

“We’re heading over to the Shore for the weekend” is a common phrase among Chesapeake Bay cruising sailors in the Mid to Northern Bay, not to be confused with “going downy ocean,” a completely different vibe. For the uninitiated sailor, there are more quiet anchorages and coves to explore on the Eastern Shore than one could visit in a lifetime. A cruiser could spend a week discovering each of the rivers described here, anchoring in a different place every night, and still not put the hook down in every cove. They’re all worth exploring! Here are five:

  1. Sassafras River
  2. Chester River
  3. Miles River
  4. Wye River
  5. Choptank River

Sassafras River

Size: 20 miles long, 97.2-square-mile watershed.
Character: Fresh to slightly brackish. Largely rural, with historic towns such as Georgetown and Fredericktown. 
What sailors seek there: The blooming of the American lotuses in mid to late July into August. Mount Harmon Plantation plans a Lotus Blossom Festival in August. 

American lotuses in bloom on Lloyd Creek near the mouth of the Sassafras River.

Chester River

Size: 43 miles long, 368-square-mile watershed
Character: Brackish. Dominated by agricultural land with small towns and villages, such as Chestertown.
What sailors seek there: Quiet coves and a feeling of going back in time. Chestertown Tea Party (usually held Memorial Day weekend) and Sultana Downrigging Weekend, also in Chestertown (around Halloween). 

Sailing Tall Ships at Sultana Downrigging Weekend
The Sultana Downrigging Festival in Chestertown, MD, draws beautiful sailing vessels. Photo by Eric Moseson

Miles River

Size: 12 miles long, 54-square-mile watershed.
Character: Brackish. Mostly rural with historic St. Michaels as a highlight.
What sailors seek there: The quaint town of St. Michaels, Chesapeake Bay Maritime Museum events (such as the Charity Boat Auction Labor Day weekend), log canoe races, and quiet coves.

Sailing log canoes
Log canoe sailing on the Miles River. Photo by Craig Ligibel

Wye River

Size: 16 miles long, 78-square-mile watershed.
Character: Brackish. Mostly rural, winds around wildlife preserve and forest at Wye Island.
What sailors seek there: Quiet, well-protected coves and nature walks at Wye Island State Natural Resources Management Area

Learn more abou the Miles and Wye Rivers and thier Riverkeeper here: Meet Elle Basset, the Miles and Wye Riverkeeper.

Sailboats at sunset on the Wye River
Sailboats at sunset on the Wye River. 

Choptank River

Size: 71 miles long, 1004-square-mile watershed.  
Character: Freshwater at the head in Delaware and brackish at the mouth. Mostly agricultural, with towns Cambridge, Oxford, and Denton.
What sailors seek there: Quiet, well-protected coves. Visits to Cambridge for dining, festivals, fuel, provisions, and marinas.

Sailing on the Choptank River
Sailing as the sun sets on the Choptank River.

Valinor’s Adventures: A weeklong cruise on the Choptank and its creeks

In May, James McKenna and his wife Koralina, a SpinSheet Century Club member, spent a week cruising their 1968 Tartan 34 C Valinor, spending several nights on the Choptank and its tributaries with their five-year-old Cavalier King Charles Spaniel, Beaker. At the end of the trip, they went through Knapps Narrows, a notoriously shallow place, and were pleased that they made it without incident with their four-foot draft. Here are a few highlights.

A sailing cruise to the Choptank River
James McKenna takes time out to read during a weeklong sailing cruise to the Choptank River and its tributaries.

Little Beckwith Creek: The square lighthouse on little island, which was serene, beautiful, well-protected. “The water did not have the algal bloom (we had in Annapolis) and looked tropical,” says Koralina.

La Trappe: There is a privately owned beach (Martin Point), where they let people beach there on the sand bar. It got rowdy as a result; although there are some anchoring holes off La Trappe. Once the powerboats cleared out it quieted down. Every boat had a dinghy and a dog.

Cambridge: They stayed in the creek near Snapper’s and took the first good long walk of the week with Beaker. There was great people watching at the bascule bridge. “They were super nice at the fuel dock at Cambridge Yacht Basin,” says Koralina.

Oxford: On a super sleepyTuesday evening, even the Scottish Highland Creamery was closed for ice cream. They anchored in Oxford near the public dinghy dock, next to the Hinckley Yard. They walked to the park across peninsula, where there were kids were swimming and also walked to the dog park.

San Domingo Creek: Here they anchored at the back of St. Michaels. There is a nice public nature park and dinghy dock less than a five-minute walk to St. Michaels (no pump out or fuel on that side)—but they did go buy ice!