The Wye River is a hidden gem behind Eastern Bay, between Kent Island and St. Michaels. A good number of people pass it by without giving is a second thought, as it’s along the way to other destination spots. Along the Wye and the Wye East Rivers you’ll find many of the views the Chesapeake is famous for; habitat for wintering waterfowl and other native wildlife, flora varying from marshland to stately old trees, as well as the sweeping slopes of carefully manicured lawns leading up to mansions on hilltops. 

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Stately homes dot the shores of the Wye River.

The Wye and the Wye East Rivers surround Wye Island, which, after the early American years of agriculture and unsustainable practices, is now maintained and safeguarded by the Wye River Natural Resources Management Area. The organization reports that, “A major emphasis at Wye Island is providing suitable habitat for wintering waterfowl populations and other native wildlife. A primary resource management objective at Wye Island is the stabilization of the 30 miles of ever-eroding shoreline.” 

The Wye Research and Education Center, the state of Maryland with the Wye River Natural Resources Management Area, and the Maryland Agricultural Experiment Station (MAES) also participate in protecting the island and the area. The island is positioned in the tidal recesses of the Chesapeake Bay, giving it the changing shoreline that both leave it vulnerable and make it a great place for wildlife habitat. 

These rivers offer access to 16-17 nautical miles of waterway for scenic slow cruising. The natural beauty along the river is abundant, and there are no less than five to six feet of water for cruising and admiring the countryside. The only restriction to navigation is a bridge with only 10 feet of clearance. The whole loop might be a great dinghy ride if you have enough gas onboard. 

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The Wye River is perfect for scenic, slow cruising.

From the mouth of the Wye River, the northern arm of the loop, there are about six nautical miles of river before the Wye Narrows Bridge. On this cruise you find Bennetts Point Landing, which acts as a great passenger pick up/drop off point, the Wye Island holly tree, a very large, 300-year-old holly tree, and the Wye River Conference Centers. The river shows the powerful dichotomy of the well-developed north shore and the naturally scenic aspects of the south shore.

From the mouth of the Wye East River, the southern arm of the loop, there are just over nine nautical miles to the Wye Narrows Bridge. Along this cruise you can see the lands of the Wye House, the plantation where Frederick Douglass was held as a slave in his boyhood; Wye Heights, a family run farm with Black Welsh Mountain Sheep whose single importation of three rams and 13 ewes forms the genetic basis of the North American flocks; and a large public boat ramp called Wye Landing. Immediately inside the mouth of the river you’ll find yourself in Shaw Bay, the wide-open anchorage where the annual Eastport Oyster Boys Concert happens each year the Saturday after Labor Day.

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Photo courtesy of Blue Moon Photography

An Outdoor Concert, Chesapeake Bay Style

At the close of each summer, for quite a few years now, the Eastport Oyster Boys do an outdoor concert, Chesapeake Bay style. No grass, no hillside, no band shell… just a great anchorage, a sea of dinghies, and a great band on a raft. And this year it’s perfect for fun and community in this time of social distancing.

In our early boating adventures on the Chesapeake, we had no idea this event was going on and decided to anchor in Shaw Bay for the weekend. We wanted to meet some friends and enjoy the beautiful scenery there. Arriving midday, we set the hook and commenced our relaxing. We got our dinghy down from its perch and took a little ride up this beautiful pastoral river. However, while we were away, the anchorage had really begun to fill up. Back on the boat, sitting on the deck chatting with our friends and watching the world go by, the anchorage began to feel mighty crowded. More and more people were out cruising in their dinghies. Not an unusual site, but there were so many on this occasion. We wondered if maybe this was a club meet up event and we were inadvertently crashing the party. However, we learned this was a very special occasion we had stumbled on.

Kevin Brooks, the founding member and guitar player for Eastport Oyster Boys, reports that about 15 or 16 years ago someone said, “Let’s put on a show.” They figured it would be loads of fun and people could come out to listen if they wanted. That first year they had about five boats, and the number of boats anchoring up has grown every year. They play on the mother barge powered by one of the guy’s trawlers with a ton of solar panels. They report their biggest crowd has been about 175 boats.

About eight years ago the event became a fundraiser for the ShoreRivers Pumpout boat organization. Cruisers sitting in any great anchorage along the Eastern Shore recognize that their pumpouts need to be taken care of, and this boat offers the free service on the Miles and Wye Rivers. The organization reports, “With your help, this boat will prevent about 20,000 gallons of concentrated marine waste from entering our waters annually.”  

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For this year's event, attendees are asked to stay in their own dinghies for the concert and to practice social distancing. Photo courtesy of Elle Bassett, ShoreRivers

At the concert each year they used to pass the hat to collect widely varying donations in support of this organization. But, you wonder, how does a free concert in a wide-open public place raise money? Originally, they had some folks cruising around in a dinghy with a crab net and people would just deposit their donations. After a year with some bad weather they decided cruising around in a dinghy to collect donations might not be the smartest plan, so they took the fundraising part of this adventure online, and the organization set up a text-to-give campaign. Check out the website donation page ( if you would like to contribute. These guys are so dedicated to the clean water cause that they will even do a dedication for a donation.

Every year, the Saturday after Labor Day, boats from all over the Chesapeake meet up in Shaw Bay for what is lovingly referred to as a slosh pit: the great music and the boaters’ community. Learn more at and Stay tuned for updates regarding the  concert at

About the Author: Elizabeth Kelch is a tree hugger, minimalist, and traveler. She, with her partner and captain, live aboard their trawler, In No Hurry, cruising the East Coast chasing good times and warm weather. You can follow their adventures and read more of her work at