Shakespeare at the Manor: Twelfth Night

07/25/2026
, 07/26/2026
6:00 pm

8:00 pm
Manor Grounds

On a warm July evening at the historic Sylvester Manor on Shelter Island, love gets wonderfully, hopelessly lost. In Shakespeare’s Twelfth Night, a shipwreck throws two twins to opposite shores, a lovesick duke can’t stop writing bad poetry, and a clever young woman disguises herself as a man — with spectacular consequences for everyone around her. Mistaken identities spiral, secret letters are planted, and a magnificently pompous household steward gets the comeuppance of a lifetime. It’s Shakespeare at his most playful and most tender, a comedy that ends in music and improbable joy. Spread your blanket on the lawn, uncork something cold, and let one of the greatest love stories ever written unspool as the summer sky dims around you. No Shakespeare experience required — just a willingness to laugh, and an evening to spare.

Directed by Allen O’Reilly and produced by Robin Aren Productions.

Seating is outdoors on the lawn so please bring a blanket or beach chair. You are welcome to enjoy your own picnic/BYOB. Bug repellent and comfortable shoes are recommended.

In the case of inclement weather, the performance will take place in the auditorium at the Shelter Island School. Seating will be first come, first served.

$40/person. Children ages 10 and under are free. Gates open at 5:30pm.

Fans of the Bard are also encouraged to attend two special events to meet the cast and celebrate all things Shakespeare.

On Thursday, July 23 at 6:30pm, the Manor will host Shipwrecked with Shakespeare, an evening of music and revels at The Shipwreck (63 S Menantic Rd, Shelter Island)! Come by to enjoy the company’s music and performances, themed drinks, and a few more surprises. All proceeds from the evening will support future seasons of Shakespeare on Shelter Island. Free to attend.

On Sunday, July 26 at 11am, the Manor will host a Shakespeare Fair at the Windmill (21 Manwaring Rd, Shelter Island), featuring special performances, treats from the farm, and fun activities for all ages! All ages welcome. Sign up today $20 per family.


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