Every fall, a fleet of schooners — large and small, new and old — gather in Baltimore to celebrate Chesapeake Bay heritage and race down the Bay to Portsmouth. With a day of sail parade in Baltimore, a start off Annapolis, and events at the finish in Portsmouth, VA, the event is for anyone interested in schooners, Bay history or a spectacle reminiscent of the age of sail.

The Great Chesapeake Bay Schooner Race has its roots in the rivalry between two great Bay ports, Baltimore and Portsmouth. In the day when trade on the Bay was sail-powered and schooners carried cargo throughout the region, the fastest boats were able to beat their competitors to the markets and often commanded the highest prices for the goods they carried. Today, the event raises money to support Chesapeake Bay education and restoration. Thirty-seven schooners participated in the 2012 event.

This year's event begins Oct. 14 in Baltimore and ends Oct. 20 in Portsmouth. Participating boats can be viewed dockside Oct. 14 in Canton at the Baltimore Marine Center at Lighthouse Point. Some of the schooners will participate in a re-enactment of the bombardment of Fort McHenry 11–12:30 a.m. Oct. 15. A parade of sail in the Baltimore Harbor is scheduled Oct. 17.

The race begins 1:30 p.m. Oct. 17 just south of the Bay Bridge. The schooners will race through the night and, depending on the weather, are expected to finish sometime on Oct.18.

Watermark Cruises of Annapolis offers tours of the Parade of Sail, the Fort McHenry Re-enactment, and the start. Learn more at www.watermarkcruises.com/. The schooner Woodwind also plans to offer a cruise to watch the race start, as well as passage during the race. Learn more at www.schoonerwoodwind.com/.

At the finish, the public can join an informal get-together at Roger Brown's in Olde Towne Portsmouth. They are welcome to mingle with the crews of the schooners that completed the race. On Oct. 19, the schooners can be viewed dockside in Portsmouth and some may be open for tours.