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Autumn in Annapolis

Autumn’s clear skies and refreshing temperatures are the perfect backdrop for an Annapolis and the Chesapeake Bay getaway, so start planning a trip that mixes the area’s sailing, seafood, and festivals with the unique sights and sounds that signal the arrival of autumn.

This season is a great time to explore the Sailing Capital of the World. Rent or charter a small sailboat for the afternoon, day, or weekend. The waters of the Chesapeake stay warm well into October, thanks to the area’s warm summer weather, and the air temps hover in the mid 60s to low 70s. In September, catch the races and regattas hosted by the Annapolis Yacht Club. In October, don’t miss the U.S. Powerboat Show and U.S. Sailboat Show at the City Dock. They’re the largest and oldest in-water boat shows in the country.

Festivals are synonymous with autumn, and Annapolis and the Chesapeake Bay has plenty of outdoor events that let you munch on caramel apples amid a spectrum of red, orange, yellow, and gold leaves. Enjoy an evening of great music at the Boatyard Beach Bash on September 25. Catch jousting, crafts, and period fare at the 22-acre Maryland Renaissance Festival through October 24. Then kick back and enjoy old-fashioned contest favorites, like hog calling, pie eating, pig racing, and livestock judging, at the Anne Arundel County Fair, held September 15-19.

While warm cider and pumpkin pie make for tasty autumn treats, they have nothing on the Chesapeake’s fresh seafood. Maryland blue crabs are at their fattest and tastiest this time of year, so be sure to attend the Maryland Seafood Festival. Held September 10-12, this event features a crab soup cookoff, crab picking contest, and crab cake eating contest, in addition to other tasty seafood prepared by the area’s top chefs and restaurants.