 A map showing the quaint & quiet town of Sherwood on Waterhole Cove and Lowes Wharf where we eventually found the waterhole.  NOAA Chart of Waterhole Cove, the town of Sherwood and Lowes Wharf. The Chesapeake bay is on the west side. Knapps Narrows is south. |  With the anchor set we watch a beautiful Sunset from Waterhole Cove of Harris Creek and the Choptank River. Photo Credit: Martina Sestakova Our sailing fleet splashed north in Harris Creek on a beam reach leaving the Choptank River in our wake. I was aboard Base Camp, my 31’ Pearson sailboat, with my trusty crew. Breezin, a Catalina 34', was just ahead. We sailed right past our usual and beautiful anchorage, Dun Cove. We continued north into 'uncharted' waters, headed to the very next cove - rich in history, adventure and intrigue. In the early 1600's explorers like Captain John Smith came to this very spot to fill water casks on tall ships like the Discovery, Godspeed and Susan Constants. The underwater springs rose up from the coves bottom allowing the ships to conveniently fill their tanks without going to land. Like many others before us, our sailing expedition aimed to drop the hook in the famed Waterhole Cove and search for that spring. Our tanks were getting close to empty. |
For our approach, we sailed just inside the aptly named Smith Point with the town of Sherwood and their public pier off our port beam. I scanned the water for signs of the ancient underwater spring. An occasional bubble of water or splash from a fish would catch my gaze as I hoped to re-discover that illusive fresh water spigot hiding below our keel. The town used to have many springs. Unfortunately they had all dried up possibly a century ago or more. But we still were in search of a 'waterhole'.
We dropped our hook about 100 yards off the shore in 7 feet of water. The land around us had a few older homes hidden in the trees along with lots of undeveloped shoreline. The town pier was in our sight. We had discovered a beautiful anchorage. However, it had very little wind protection. My boat Base Camp was now rafted up with our buddy Breezin, an immaculately maintained and skillfully sailed boat. We had rafted together many times before that we knew the drill including exact location for fenders, how to run the lines and what drinks/appetizers would appear from each cabin once the sun began to set.
 Sherwood town pier and dinghy tie-up. Photo Credit: Martina Sestakova |  Breezin, a Catalina 34, and Base Camp, a Pearson 31, rafted up in Waterhole Cove for an overnight adventure including finding that illusive Waterhole. Photo Credit: Martina Sestakova |
The search for the waterhole continued. Perhaps it was a short half mile walk up quaint and peaceful country roads. Our expedition was now searching for Lowes Wharf Bayside Grill 'waterhole.
After a short dinghy ride to the town pier our expedition of 3 sailors was now travelling on foot. We would stretch our legs and continue the adventure to find that illusive waterhole now hoping for frosty cold brews and orange crushes.
From the end of the pier we continued our journey up Sherwood Landing Road and eventually turned right on Lowes Wharf Road. We ran into locales tending to their gardens outside charming homes. After crossing Tilghman Island road and walking just a short distance, we discovered our waterhole, The Bayside Grill. Views of the Chesapeake Bay from their outdoor sand bar were picturesque with Poplar Island in the background. The bar was empty since it was a weekday, but I could imagine the spring break like scene of volleyball and corn hole being played with music blaring from speakers on the now empty stage. With a few drinks at the bar, the expeditions tanks were finally filled. We were ready to set out for the return walk back to our dinghy tied up at the pier, dinner on our boats and a few more drinks to finish out a perfect night and successful expedition in search of the waterhole.
After a short dinghy ride to the town pier our expedition of 3 sailors was now travelling on foot. We would stretch our legs and continue the adventure to find that illusive waterhole now hoping for frosty cold brews and orange crushes.
From the end of the pier we continued our journey up Sherwood Landing Road and eventually turned right on Lowes Wharf Road. We ran into locales tending to their gardens outside charming homes. After crossing Tilghman Island road and walking just a short distance, we discovered our waterhole, The Bayside Grill. Views of the Chesapeake Bay from their outdoor sand bar were picturesque with Poplar Island in the background. The bar was empty since it was a weekday, but I could imagine the spring break like scene of volleyball and corn hole being played with music blaring from speakers on the now empty stage. With a few drinks at the bar, the expeditions tanks were finally filled. We were ready to set out for the return walk back to our dinghy tied up at the pier, dinner on our boats and a few more drinks to finish out a perfect night and successful expedition in search of the waterhole.
 Our walk along the peaceful and less travelled Lowes Wharf Road in Sherwood, Maryland. |  Sun setting over Sherwood, Maryland, as we enjoyed a beautiful evening anchored in Waterhole Cove. |
Aboard Base Camp, we are always looking for new and different adventures. This may include exploring a quaint shore-side town for local food and drinks after a long hot day on the water. Waterhole Cove was a perfect adventure mixture of water and shore-side time. Visiting a local attraction by boat always make the adventure much more fun.
Wish to join us on an adventure? Go to our Sail with us page and inquire.
Wish to join us on an adventure? Go to our Sail with us page and inquire.
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