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Return To The Chester

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The rivers of Chesapeake Bay are a cruiser’s paradise. The Chester River, just across the bay from Annapolis, Maryland, has always been one of our favorites, meandering as it does back into Maryland’s Eastern Shore.

In our younger, pre-retirement days, my husband Gene and I had been on the Chester many times, but since becoming full-time cruisers, we had followed the call of the Great Loop, the Bahamas, and the Keys, giving us little chance to spend time on our home cruising waters, the Chesapeake Bay. This fall, before heading south, we decided to take a side trip back up the Chester. We were looking forward to re-discovering the charm of the Chester aboard our retirement home, a Great Harbour Trawler named Lo Que Se A, meaning “whatever” in Spanish.


The Chester River’s entrance, just northeast of the Bay Bridge, is wide, making it easy to dodge the ever-present crab pots and fishermen in their small boats sitting with rods poised, waiting for that big striper to take their bait. Just inside its mouth is Kent Narrows, a kind of “gateway” to the Eastern Bay. Even though a new high-rise bridge has been constructed at the Narrows (so that the beach traffic is no longer inconvenienced by the drawbridge openings), the boating community is not so lucky. The old drawbridge is still in place, opening its very narrow passageway every half hour, and still causing boating back-ups.

Kent Narrows is not really a town, but rather a bustling waterfront community, abundant in marinas, restaurants, and repair facilities. On any given weekend during boating season, sounds of Jimmy Buffet and reggae steel drums waft from the open-air bars packed with weekend revelers.

We passed on the party scene, and went on to anchor in the first of our favorite anchorages;—Queenstown Creek. We remembered that even though well marked, its entrance was a little tricky. Our notes told us to line up the boat’s bow with the left side of the white house at the other end of the entrance channel. We did, and cruised right in. Once inside, just abreast of the red, a turn to port and five minutes put us ready to drop our anchor in a totally protected creek, wooded to the banks, where wildlife abounds. There were several great blue heron rookeries hidden in the treetops, and at dusk we caught sight of a deer down at the water’s edge. We were also privileged to see a majestic, full-grown bald eagle dip down and harvest a fish for dinner. The next day, before we pulled anchor, we set off in the dink through a canopy of ancient oaks and explored the upper creek. Quiet abounds!


Our next-favorite spot was on the more open Corsica River. The Russian Embassy’s retreat at its mouth is always a reminder that our nation’s capital, with its international politics, is not far away. The Russian retreat has been the scene of several important negotiations, but with the end of the Cold War, it has lost much of its mystique.

The Corsica is bordered by farmland that slopes gently down to its shores, and we waved at the farmer working his fields astride his John Deere, as a low-flying crop duster buzzed us overhead.

One of the things that make the Chester River such a favorite is its depth. Sailboats flock there because even on a day without wind there is plenty of room to tack without having to worry about grounding or getting in the path of faster moving powerboats.

Beyond the Corsica one must make the decision to follow the main channel up to Chestertown or head to port into the forked entrance of Langford Creek. We opted for Chestertown first. We decided to treat ourselves to a marina, which made provisioning and exploring easier. Many boats anchor in the river just off the town boardwalk but be mindful of the river’s current and set your anchor well before leaving the boat to explore. We’ve heard many tales of returning dinghies having to chase down the mothership as it dragged its anchor down river.


Not only is Chestertown a wonderful example of an early American river port, it is home to Washington College, named for our first president, who sat on its governing board. Established in 1782, it is the 10th oldest college in America and its campus is an integral part of Chestertown. It was heartening to see that all through the town, street after street of old homes have been, or are being restored, and everywhere huge ancient sycamores, oaks, and maples shade the old brick sidewalks. The town is well laid out and it was fun to follow the walking tour map that we picked up. Many of the homes that front the river have widow’s walks, where historically, wives could keep a solitary vigil down river waiting for sight of their captain’s ship.

Chestertown embraces its water heritage. They have actually built and launched a replica of a small schooner, Sultana, which is used for maritime education. Each year on Memorial Day weekend, they have their own Tea Party, showing their solidarity with the citizens of Boston by recreating the storming of the Brigantine Geddes.

After bidding farewell to this quaint little town on the Chester, we backtracked down to Langford Creek. A favorite anchorage is just off Cacaway Island. The water is 8 feet almost to shore and even though the island is posted with “no trespassing” signs, its crescent shape gives good protection from the northwest and a great “happy hour” view from the cockpit. The eastern fork of Langford is the more pristine, although even it is much more built up than we remembered.


After a perfect evening spent reminiscing about our earlier boats and many cruises on this wonderful river we turned in, leaving the ports and hatches open, lulled to sleep by the sounds of the river creatures. The next morning as we pulled the anchor, we decided to spend one last relaxing day slowly cruising as far up as we could to the headwaters, just enjoying the scenery, before heading back out to the busy Chesapeake.

It had been a great fall cruise. The warm temperatures were unprecedented, the winds calm, and the Chester still as welcoming as we'd remembered.