America 2.0 at the beginning of the Great Chesapeake Bay Schooner Race, 2011. Photo by Joe Elder aboard the Schooner Spirit of Independence. Olde Towne Portsmouth once again hosted the finale of the 23rd Annual Great Chesapeake Bay Schooner Race from Baltimore Mayland with 37 participating schooners. Here is a photographic study of these exceptional sailing vessels docked along Olde Towne's waterside. Enjoy! An 18th century cannon stands sentinal in front of the schooner "Mystic Whaler" docked along side the High Street basin. Photo by Joe Elder. HISTORY Schooner "Adventurer" figurehead. Photo by Joe Elder. Schooner racing on the Chesapeake Bay is rooted in the trade rivalry between Baltimore, Maryland, at the northern end of the Bay, and Portsmouth/Norfolk, Virginia, at the southern end. The fastest sailing vessels delivered goods and people to their destinations and often garnered the best price for their cargo by beating slower schooners into port. Ov