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Stumblday's picks: upcoming booze cruises, sunset sails, and boat parties around New York Harbor.
5 picks · checked Oct 5
Schooner Adirondack, Chelsea Piers (Pier 62), Chelsea, ManhattanChelsea, Manhattan
Sail an 80-foot schooner up the Hudson under the George Washington Bridge to the 400-foot Palisades cliffs as the leaves start to turn.
Schooner Adirondack, Chelsea Piers (Pier 62), Chelsea, ManhattanSail an 80-foot schooner up the Hudson under the George Washington Bridge to the 400-foot Palisades cliffs as the leaves start to turn.
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St. George Theatre, St. George, Staten IslandTdorante10 · CC BY-SA 4.0 · Wikimedia CommonsSt. George, Staten Island
Seven-piece SoCal yacht-rock band Yachtley Crew, signed by Jimmy Buffett's label, sails into St. George's historic theater.
St. George Theatre, St. George, Staten IslandTdorante10 · CC BY-SA 4.0 · Wikimedia CommonsSeven-piece SoCal yacht-rock band Yachtley Crew, signed by Jimmy Buffett's label, sails into St. George's historic theater.
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Schooner Adirondack, Chelsea Piers (Pier 62), Chelsea, ManhattanChelsea, Manhattan
A two-hour sunset sail on an 1890s-style 80-foot schooner past One World Trade, Ellis Island and the Statue of Liberty, engines off.
Schooner Adirondack, Chelsea Piers (Pier 62), Chelsea, ManhattanA two-hour sunset sail on an 1890s-style 80-foot schooner past One World Trade, Ellis Island and the Statue of Liberty, engines off.
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Lou Gehrig Plaza: Lou Gehrig Plaza E. 161st Street between Walton Ave and Grand Concourse, BronxLou Gehrig Plaza: Lou Gehrig Plaza E. 161st Street between Walton Ave and Grand Concourse, Bronx
A temporary structure lands on Lou Gehrig Plaza, the public square beside Yankee Stadium named for the first baseman they called the Iron Horse.
Lou Gehrig Plaza: Lou Gehrig Plaza E. 161st Street between Walton Ave and Grand Concourse, BronxA temporary structure lands on Lou Gehrig Plaza, the public square beside Yankee Stadium named for the first baseman they called the Iron Horse.
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Classic Harbor Line, Chelsea Piers (Pier 62), Chelsea, ManhattanChelsea, Manhattan
A live jazz trio plays Gershwin, Ellington and Motown on a 1920s-style yacht cruising past the Statue of Liberty and Ellis Island.
Classic Harbor Line, Chelsea Piers (Pier 62), Chelsea, ManhattanA live jazz trio plays Gershwin, Ellington and Motown on a 1920s-style yacht cruising past the Statue of Liberty and Ellis Island.
Add to calendarThis list covers the weekend of Oct 9–12, 2026, and it refreshes automatically every week.
Stumblday curates and re-ranks NYC events each week from official venue and city sources — so you get a short, vetted shortlist instead of an endless calendar.
