Schooner Days 2010, Portsmouth, Virginia October 15-16, 2010 Schooner Days is a celebration of the world’s largest gathering of schooners along the waterfront of Olde Towne Portsmouth, Virginia. It's held this year in conjunction with the 21st Annual Great Chesapeake Bay Schooner Race from Baltimore to Portsmouth- racing to save the bay ! Schooners LADY MARYLAND and LIBERTY CLIPPER at Portsmouth, Virginia's Schooner Days. This two-day celebration offers numerous maritime-related activities along the seawall and at the High Street Landing; many are free to the general public. Schooners line the seawall at Portsmouth, Virginia's High Street Landing The Portsmouth waterfront from North Landing to beyond the High Street Landing will showcase over 40 schooners from local and distant ports and is considered the largest gathering of schooners in the world. A gathering of great vintage wooden schooners are clustered together in Olde Towne Portsmouth for Sc...