Watch monthly sail races aboard CBMM’s Winnie Estelle

The Chesapeake Bay Maritime Museum is pleased to be able to offer a new way to experience the Chesapeake this year, with a monthly series of Wednesday Night Racing Spectator Cruises inviting the public to spend an evening on the Miles River watching sailboat races from the deck of CBMM’s 1920 buyboat Winnie Estelle.

With each set to depart from CBMM’s campus in St. Michaels, Md., cruises are scheduled for 5:30–7:30pm on June 2, July 7, and Aug. 4, and 5:15–7:15pm on Sept. 1 and Oct. 6.

These spectator cruises offer a great introduction to sailboat racing in a casual but competitive atmosphere. For extra fun, sign up to watch the annual James Wilson Round the Island Race on Aug. 4, where all boats race a set 6.8-mile course around Herring Island; and the Oct. 6 race, where the fleet celebrates the end of the sailing season with a competition for the “Best Dressed” award.

The cost to participate in one of CBMM’s Wednesday Night Racing Spectator Cruises is $20 per person, with a 20% discount for CBMM members. To register, visit

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