My son Nathan and I built an 1890s Chesapeake Bay crabbing skiff amid the cornfields of Tuckahoe Neck.  More about her construction and preservation is here.

We launched Caroline C. at Denton in 2003 and sailed her on the Choptank and Tuckahoe Rivers before Nathan moved her to Madison.  He sails her now on lakes around Wisconsin.

Caroline C. may be the last sailing workboat to ply the Choptank. But she wasn’t the first. The upper Choptank and Tuckahoe Rivers have a 300-year heritage of both shipping by sail and shipbuilding.


Bugeyes at the West Denton wharves about 1904.

Caroline C. returned to her home waters in June 2019 for a week of sailing on the Choptank and rowing near the tidal head of the Tuckahoe at Hillsboro.  We launched her from Denton on a blustery Friday morning.

The tide was very high at launch. This would be good for catching the ebb tide if winds were slack. But winds were forecast from the northwest at 20 kts, gusting to 30 kts.  We expected to be shielded from most of this wind by the high banks on the west side of the Choptank.  So Nathan rowed us under Denton Bridge and past Joppa Wharf before hoisting sail.

Our deadrise skiff was designed for crabbing in shallow waters.  This allowed us to skim the edge of the marsh opposite the wind shadow of the high banks.

We had to watch carefully for wind gusts through gaps in the wooded shoreline and along wider stretches of the Choptank.

We were doing better than 6 kts when we passed Wing Landing on the middle Choptank.

Caroline C. did the 13-mile run from Denton to Kingston Landing in just 5 hours – a rare day of sailing on the narrow Choptank.

Read more here about the history
of sailing vessels and shipbuilding
on the Choptank and Tuckahoe