What To Do

Irving's Legend
2025-10-03 | Washington Irving’s Sunnyside, 3 W Sunnyside Lane, Irvington, NY, 10533, United States
Irving’s Legend
Jonathan Kruk casts a spell with dramatic performances of Washington Irving’s classic tale classic tale, The Legend of Sleepy Hollow. Live music and sound effects by Jim Keyes and an appearance from the Headless Horseman himself, plus a cast of shadowy supporting characters, make this a spooky spectacular experience for all ages.
From October 3 to November 1.
Fridays & Saturdays > Performances at 6, 7:30, 9pm
Sundays & Monday > Performances at 5, 6:30pm
Special Hours
Sunday, Oct. 12 > Performances at 6, 7:30, 9pm
Washington Irving’s Sunnyside

Tarrytown Music Hall: Marty Stuart and His Famous Superlatives
2025-10-17 20:00 (America/New_York) | CT
Tarrytown Music Hall: Marty Stuart and His Famous Superlatives with Special Guest Richard Shindell
Marty Stuar, who was featured in Ken Burns’ 13-hour Country Music documentary, got his start when he was invited to tour with Lester Flatt at the age of 14. He then toured with Johnny Cash’s road band before beginning work as a solo artist in the early 1980s. A five-time Grammy Award-winner, Stuart has recorded over 20 studio albums, and has charted over 30 times on the Billboard Hot Country Songs charts. His highest chart entry is “The Whiskey Ain’t Workin'”, a duet with Travis Tritt.
Tarrytown Music Hall

White Plains Performing Arts Center: Jagged Little Pill
2025-10-03 19:30 | White Plains Performing Arts Center
White Plains Performing Arts Center: Jagged Little Pill
The Tony & Grammy Award Winning Musical
Jagged Little Pill, the musical inspired by the Alanis Morissette’s album of the same name ,was nominated for 13 Tony Awards and won not only multiple Tony Awards but also the Grammy Award and two Drama Desk Awards. It was even a NY Times Critic Pick!
White Plains Performing Arts Center

Rosen House Concert Series: Stella Cole
2025-10-17 19:30 | Caramoor
Rosen House Concert Series: Stella Cole
Though you might know her from her viral social media success (1.6 million followers and videos that have reached an astonishing 27 million views), nothing compares to experiencing Stella breathing new life into jazz standards and golden-age classics. Treat yourself to a night with one of today’s most captivating young vocalists.
Caramoor

Bedford Playhouse Screening with Special Guests
2025-10-17 19:00 | Bedford Playhouse, 633 Old Post Road, Bedford, NY, 10506, United States
Oscar with Special Guests Chazz Palminteri and Peter Riegert
Watch a screening of the cult classic comedy, Oscar, from John Landis, the director of National Lampoon’s Animal House, The Blues Brothers and Trading Places followed by a Q&A with two of its stars – Chazz Palminteri and Peter Riegert.
The film also stars Sulvester Stallone, Marisa Tomei and Ornella Muti.
Bedford Playhouse

The Great Jack-O-Lantern Blaze
2025-09-29 07:00 - 19:00 | Van Cortland Manor, 525 S Riverside, Croton On Hudson, NY, 10520, United States
The Great Jack-O-Lantern Blaze
Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site. Complete with synchronized lighting and an original soundtrack, this immersive, one-of-a-kind event is not to be missed!
This event is held on select nights from September 121 to November 16.
Including: seven nights a week from September 29 to November 2.
The Great Jack-O-Lantern Blaze

Harvest Moon Farm & Orchard: Mystic Moon Spooktacular Experience
2025-09-19 | Harvest Moon Farm & Orchard
Harvest Moon Farm & Orchard: Mystic Moon Spooktacular Experience
Unlike traditional Halloween attractions, Mystic Moon trades fright for wonder, inviting guests into a world of moonlit magic. This 40-minute adventure is crafted for both children and adults, weaving together an atmosphere that’s equally mystical and enchanting.
Along the way, guests will encounter enchanting scenes, countless photo ops, and a touch of mystery among theatrical lighting to keep the experience magical.
After the trail, there’s festive drinks and seasonal treats under the orchard’s big tent.
Weekends and Monday holidays from Friday, September 19 to Saturday, October 13.
Daily from Thursday, October 16 through Saturday, November 1: Check times.
Harvest Moon Farm & Orchard

Twilight Village at Sleepy Hollow Country
2025-10-03 | Philipsburg Manor, 381 N Broadway, Sleepy Hollow, NY, 10591, United States
Twilight Village at Sleepy Hollow Country
As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, and eerie encounters around every corner.
Philipsburg Manor

Spirits of Sleepy Hollow Country
2025-10-03 | Philipsburg Manor, 381 N Broadway, Sleepy Hollow, NY, 10591, United States
Spirits of Sleepy Hollow Country
A Night of Legendary Magic Featuring Mark Clearview & Nick Wallace
Join Sleepy Hollow Coiuntry’s master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda, Major Andre, and the Headless Horseman himself!
Oct 3 – Nov 1: FRIDAYS-SUNDAYS + Columbus Day
Fridays & Saturdays
Performances > 2*, 6, 7:30, 9:00pm
Sundays & Monday
Performances > 3:30, 5, 6:30pm
Philipsburg Manor

The Palace Stamford: John Cleese Not Dead Yet — The Holy Grail at 50
2025-10-16 19:30 | The Palace Stamford, 61 Atlantic St., Stamford, CT, 06901, United States
The Palace Stamford: John Cleese Not Dead Yet — The Holy Grail at 50
John Cleese celebrates 50 years of Monty Python and the Holy Grail. This once-in-a-lifetime event features a special screening of the beloved cult classic, followed by an uproarious conversation and audience Q&A with Cleese himself, where he’ll share behind-the-scenes stories, wit, and wisdom—assuming he remembers any of it.
The Palace Stamford

The Bedford Playhouse Live Music
2025-10-16 19:00 | The Bedford Playhouse, 633 Old Post Rd., Bedford Village, NY, 10506, United States
The Hudson Valley Wind Quintet’s Tribute to The Movies
The Hudson Valley Wind Quintet (flute, oboe, clarinet, bassoon, French horn) performs an evening of memorable music inspired by great films! Including, The Nightmare Before Christmas, Dunkirk, The Unbearable Lightness of Being, Aladdin, The Sound of Music, Up, The Terminal, and Beauty and the Beast.
The Bedford Playhouse

Katonah Classic Stage: Miss Julie/Venus in Fur
2025-10-14 19:00 | Whippoorwill Theater
Katonah Classic Stage: Miss Julie/Venus in Fur
Katonah Classic Stage present a bold pairing of Strindberg’s searing classic Miss Julie and Ives’ seductive dark comedy Venus in Fur — two riveting explorations of power, desire, and control, in repertory in October. The plays will be performed by the same cast and on the same stage but on alternate nights beginning Tuesday, October 14 through Sunday, November 2.
Katonah Classic Stage

Jazz Great Houston Person at The Schoolhouse Theater
2025-10-12 19:00 | The Schoolhouse Theater
Jazz Great Houston Person at The Schoolhouse Theater
Jazz icon Houston Person has performed with the greatest names in jazz history, from Etta Jones to Ron Carter.
You can hear him perform an evening of swing, ballads, and soulful standards at the intimate 99-seat Schoolhouse Theater in Croton Falls.
The Schoolhouse Theater

Emelin Theatre: Ailey II
2025-10-12 19:00 | Emelin Theatre
Emelin Theatre: Ailey II
Artistic Director Francesca Harper brings fresh perspectives to Mr. Ailey’s legacy, while nurturing new creative voices and propelling the company forward.
“Off-the-charts energy.” -The New Yorker
Emelin Theater

The Purchase PAC: Endea Owens and The Cookout
2025-10-12 19:00 | The Performing Arts Center Purchase College, 735 Anderson Hill Rd., Purchase, Purchase, NY, 10577, United States
The Purchase PAC: Endea Owens and The Cookout
Hot off her 2025 summer debut at Caramoor… Endea Owens and The Cookout take the stage at The Purchase PAC.
Known as one of Jazz’s most dynamic emerging artists, Endea Owens performed with Wynton Marsalis, Jennifer Holliday, Diana Ross, Rhonda Ross, Solange, Jon Batiste, Jazzmeia Horn, Dee Dee Bridgewater, and Steve Turre, to name a few.
The Purchase PAC

Old Rhinebeck Aerodrome Air Shows
2025-10-04 14:00 | Old Rhinebeck Aerodrome Air Shows, 9 Norton Rd., Red Hook, NY, 12571, United States
Old Rhinebeck Aerodrome Air Shows
America’s first flying museum of antique aircraft is just a short drive away. On weekends the museum presents a History of Flight and a WWI Dogfight Spectacular show. You can register for a bi-plane ride too.
Old Rhinebeck Aerodrome
