Summer is the peak—and most expensive—time to visit the Chesapeake Bay, as the season for swimming, fishing, boating, hiking, cycling, and kayaking comes into full swing. Summer also brings the regatta season, including the Leukemia Cup Regatta and Vintage Race Boat Regatta in June, the Cambridge Powerboat Regatta in July, and the Annual Governor’s Cup Yacht Race and Hampton Cup Regatta in August.
Spring and fall are also great seasons for visiting the bay—especially May, when the trees and flowers burst into full bloom but school is still in session and the bugs are not yet in full force. September’s calendar is full of crab and oyster festivals, and the fall foliage starts to become dramatic.
In October, the annual and extremely well-attended Mid-Atlantic Small Craft Festival in St. Michaels showcases hundreds of vessels handcrafted by amateur and professional boat builders. Don’t miss Sunday’s swap meet, where loads of nautical items are sold and bartered.
Winter is best for bird-watching, when migrating geese, ducks, and swans arrive from the north. It’s also the least-expensive season, though many businesses in smaller, tourism-focused areas close for the winter (typically the Monday after Thanksgiving until the Monday after Easter). Be sure to call ahead. No matter the season, midweek travel tends to be cheaper.