October 13-19, 2014 From Baltimore, Maryland, to Portsmouth, Virginia Schooners underway at the beginning of the Great Chesapeake Bay Schooner Race. There are schooners here, there and just about everywhere participating in the Great Chesapeake Bay Schooner Race (GCBSR). The 25th annual race begins Thursday, October 16th on the south side of the Chesapeake Bay Bridge near Annapolis, Maryland. The schooners race throughout the afternoon and night into the next day to their designated finish line. For classes A and AA, the finish is an east-west line at Thimble Shoal Light and classes B and C finish at Windmill Point. Then they proceed on to docking in Portsmouth, Virginia along the quaint historic seaport's basins and seawall. Schooners rafted together at the High Street Landing at the end of the Great Chesapeake Bay Schooner Race. Photo by Joe Elder. With 34 entries in this year's race represented from all around the Chesapeake Bay and as far away as Key West, Florida, they