Gloucester Fishermen's Memorial

The bronze figure known locally as "Man at the Wheel" has stood at the entrance of Stacy Esplanade since 1925, when it was cast to mark Gloucester's 300th anniversary. Sculptor Leonard Craske — who spent hours aboard working schooners sketching and photographing fishermen before submitting his design — posed the figure braced at the wheel, dressed in oilskins, as if driving into a windstorm toward dangerous rocks. The statue faces out over Gloucester Harbor, and surrounding it are bronze plaques carrying the names of the 5,368 men recorded as lost at sea since the city's founding in 1623. Added to the National Register of Historic Places in 1996, it remains a working memorial: flowers appear at the base when a local vessel goes down.

The esplanade itself is an easy walk from street parking along Western Avenue, which is Route 127 — the same road that carries the Cape Ann loop north toward Rockport. Rolling out from here, riders pick up the saltwater scenery almost immediately: the harbor, active fish piers, and the rocky coastline that defined the trade the memorial honors. The loop returns via Route 127A, so the statue is both the send-off and the logical close of the ride.