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Cruising the Sassafras, this time on my terms

Last month I wrote about my “managed” cruise to the Sassafras River in 1973, conducted under the direction of a Washington newspaper editor who knew nothing of cruising, sailing or Chesapeake Bay. Herewith is the promised account of my independent cruise last September to this lovely freshwater river on Maryland’s Upper Eastern Shore — this time carried out with no outside interference.

Jack Sherwood

For me, cruising means sailing at leisure to undetermined locations, ideally in 6- or 8-hour legs, but power is an option when it’s forced upon me. Because I prefer single-handing, I am able to change course on a whim with no consultation and without disappointing anyone since no one is expecting me anywhere.

My unwritten rule is to cancel a cruise if there’s no wind, but I am patient for an hour or so of stillness with all means of propulsion disengaged. To kill this idle time I sometimes begin some minor boatwork project, which seems to trigger a flat sea to darken in the distance with a developing breeze.

Ignoring currents while otherwise preoccupied led to an unwelcome situation at the beginning of this cruise while wallowing off Tolly Point at the mouth of the Severn River. Surrounded by a field of crab pot floats, my boat suddenly came to a dead stop after snagging a line in about 5 feet of water and becoming one with the float bobbing inside the outboard well. There was no choice but to don a life jacket and leap off the stern with a Leatherman knife to confront the wrapped line.

I ducked underwater several times in an unsuccessful attempt to untangle the mess and eventually had to cut the line. (Thankfully, no crabbers were around.) By that time a southerly had arrived, moving the boat north on a strong flood tide. I held on to a line attached to the telescoped ladder mounted on the transom and moved the rudder with my foot to head the boat into the wind. With a special grab line rigged temporarily across the lazarette hatch, I pulled myself aboard from a standing position on the ladder. Once safely in the cockpit I steered away from the field of floats, rolled out the jib and began sailing. This was the only physical challenge I confronted during the cruise, although I would encounter a disturbing problem a few days later while homeward-bound.

That new southerly went soft beyond Love Point at the mouth of the Chester River, giving me the choice of swinging east on a reach toward Chestertown or continuing north under power. I was focused on the Sassafras, so I continued north, motoring past Rock Hall, Tolchester Beach Marina and Fairlee Creek to my overnight destination at Worton Creek Marina, some 28 miles from Annapolis.

The Sassafras River provides a delightful backdrop for cruising (This view is looking toward the mouth.)

The route north along the Eastern Shore is marked by a busy shipping lane, but one must be wary of cargo carriers moving silently at speed, sometimes quite close to shore. Sheltered Worton Creek is difficult to find when approaching from the south because its narrow entrance is totally concealed around Handy’s Point. Once inside this hurricane hole, there are two marinas and limited anchoring depths. At dusk, I was in the mood for oysters at the Harbor House Marina, so I tied up at a bulkhead and remained there for the night under a brilliant full moon.

A very light southerly began the next morning, but I was only 8 miles from Howell Point at the wide mouth of the Sassafras and it was just 12 more to the busy harbor of Georgetown, where the river ends for most cruisers. However, a small drawbridge at Route 213 opens on demand to two more miles of navigable river. It was worth a side trip here just to visit the colorful Gregg Neck Boatyard, which dates from the late 1950s. Owned by the Westcott family since 1979, it is a small, friendly operation, and strangers are welcome for short walkabouts. Anyone who likes jam-packed boatyards with character, character boats and characters is in for a treat here.

After passing the beach-based 28-foot-high flasher, it’s almost 6 miles to the first mark, where the river narrows considerably. Beyond that flashing red, Turner Creek to starboard offers the first anchorage, but its entrance is narrow and tricky. Around Knight Island, on the river’s north side, McGill and Back creeks are well protected with some deep water, but they are a magnet for water skiers, who manage to disrupt the serenity on weekends.

Woodland Creek, farther along and to starboard, is the locale of the wooded, uninhabited Daffodil Island, which is worth exploring after a dinghy landing on a sandy beach. I anchored near there overnight but did not go ashore. The early weekend evening was not a quiet one because of the powerboats returning to Georgetown marinas and leaving rolling wakes. Fredericktown is on the north side of the deepwater river, and Georgetown is on the opposite side, but most boaters refer to the area as Georgetown.

I tied up one afternoon at the Georgetown Yacht Basin, which has 250 slips and is adding 50 more covered slips for yachts from 45 to 110 feet ( I walked up a high hillside with many steps to the historic Kitty Knight House Inn and Restaurant, where I had a pricey lunch on an outside terrace with an expansive view of most of the harbor and the river beyond. During the War of 1812 British troops under the command of Adm. George Cockburn set fire to most homes in the town but spared the Knight house because of the brave owner’s efforts to douse the small fires the Brits were trying to create.

The 42-mile trip back to Annapolis in a dead calm was much swifter than I expected because of a strong ebb tide that laid navigation markers hard over. I was off the Plum Point silo, between Still Pond and Worton Point, before I realized it. Boaters should be aware of several unnerving 6-foot spots that ripple with wavelets, as if crossing a sandbar. It was quite hazy and rather mysterious in the middle of the Bay as I headed south toward the Chesapeake Bay Bridge, invisible in the distance. I felt almost lost at times, but with the Eastern Shore to port, the Western Shore to starboard and south dead ahead, that could hardly happen.

A quarter of the way home, moving at all of the speed a 5-hp Tohatsu outboard can generate, I began taking on serious water that caught my attention when it rose above the cabin floorboards. Hand-pumping at 45 strokes a session was required every 20 minutes or so to keep up with the flow, and I was quite exhausted upon arrival in Spa Creek as night fell.

The next day at my dock I looked into the situation and discovered that I could move a wall of the outboard well on which the motor is mounted on a block. Apparently a crack opened up under stress and allowed water into the cabin. At this writing I am hoping that Muller Marine on Back Creek in Annapolis, which has experience with this issue, can take on the repair at the busiest time of the year for boatyards. Oh, well, Erewhon is 50 years old, after all, and my bony framework is getting a little brittle, too.

Jack Sherwood is writer at large for Soundings.

June 2013 issue