Wednesday Night Racing
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Woodwind and Woodwind II will be racing every Wednesday night when there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:40 pm, and then sail on a set racecourse.
2026 Wednesday Race Nights: April 22 - August 26.
No racing on July 1.
Aboard each Woodwind:
We will be serving Devil’s Backbone Orange Smash cocktail ($7.00 each) along with all of our local craft beers, wine, and bubbly.
On each boat, one lucky raffle winner will receive a free promotional T-shirt. After the exciting race, you will receive a Devil’s Backbone free drink voucher to be used at the Boatyard Bar & Grill a few short blocks away when you buy food. You can use it on Devil’s Backbone Beer or Smashes.
Tickets are $79.55 per person (the same price as our weekly sunset sails), and include a complimentary soft drink or bottled water. Tickets are on sale now for all 2026 sailing dates.
2026 Wednesday Race Nights: April 22 - August 26.
No racing on July 1.
Aboard each Woodwind:
We will be serving Devil’s Backbone Orange Smash cocktail ($7.00 each) along with all of our local craft beers, wine, and bubbly.
On each boat, one lucky raffle winner will receive a free promotional T-shirt. After the exciting race, you will receive a Devil’s Backbone free drink voucher to be used at the Boatyard Bar & Grill a few short blocks away when you buy food. You can use it on Devil’s Backbone Beer or Smashes.
Tickets are $79.55 per person (the same price as our weekly sunset sails), and include a complimentary soft drink or bottled water. Tickets are on sale now for all 2026 sailing dates.
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Where is it happening?
80 Compromise Street, Annapolis, MD, United States, Maryland 21401
Event Location & Nearby Stays:
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Host or PublisherSchooner Woodwind: Annapolis Sailing Cruises












