HVSF was founded by Melissa Stern and Terry O’Brien in September 1987 with an outdoor production of A Midsummer Night's Dream at Manitoga, home of industrial designer Russel Wright, in Garrison, New York.
The following year, Boscobel House and Gardens agreed to host HVSF's mainstage season on the estate's expansive grounds, and that summer's production of Shakespeare's As You Like It was performed under a tent overlooking the Hudson River.
The Hudson Valley Shakespeare Festival was the subject of a one-hour documentary and two hour film of a performance of Twelfth Night which premiered on the PBS affiliate WNET on September 18, 2008.
In 2016, the festival produced a community-driven production of Thornton Wilder's Our Town with a cast of about 40 citizen actors from the Hudson Valley region, directed by John Christian Plummer.
The stage, a rough patch of dirt that was on the same level as the first few rows of the audience, receding into lawns with a view[5] of the Hudson River and West Point in the distance.
[11] The Wall Street Journal hails it as, "The most purely enjoyable summer Shakespeare festival in America," while The New York Times comments, "If anyone wonders about the future of live theater or asks where the audience is, the answer is 'Under that tent.