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Functional Fall: Handled With Care @ Clay Art Center (Port Chester) September 1-October 17
Westchester Soccer Club Game @ Stadium at Memorial Field (Mount Vernon) September 2
Fireworks at Playland Every Friday night through September 4
Bedford Music Festival @ Caramoor (Katonah) September 6
Sunset Soirée at The Overlook @ Lyndhurst (Tarrytown) September 10
Autumn Glow Festival @ Glen Island Park (New Rochelle) September 11-November 1
Yorktown Grange Fair (Yorktown Heights) September 11-13
9th Annual Wakanda Celebration @ Wakanda Cultural Campus (Mount Vernon) September 12
Up the River Blues Festival @ Louis Engel Waterfront Park (Ossining) September 12
Big Ocean K-pop @ Caramoor (Katonah) September 13
Arab-American Cultural Heritage Celebration @ Kensico Dam Plaza (Valhalla) September 13
Bicycle Sundays @ Bronx River Parkway September 13, 20, 27
Hispanic Heritage Month Featured Artist: Breana Ferreira @ Clay Art Center (Port Chester) September 15-October 17
Westchester Soccer Club Game @ Stadium at Memorial Field (Mount Vernon) September 16
Dionne Warwick Over and Out Farewell Tour @ Paramount Hudson Valley Theater (Peekskill) September 17
The Great Jack O’Lantern Blaze @ Van Cortlandt Manor (Croton-on-Hudson) September 18-November 8
Legendary Tours @ Washington Irving's Sunnyside (Irvington) September 18-November 8
An Evening with John Cusack @ Paramount Hudson Valley Theatre (Peekskill) September 18
Fall Crafts @ Lyndhurst (Tarrytown) September 18-20
The Capitol Theatre 100th Anniversary Celebration @ The Capitol Theatre (Port Chester) September 19
'Chasing the Headless Horseman' Book Talk @ Lyndhurst (Tarrytown) September 19
75th Annual Herb Fair & Market @ Caramoor (Katonah) September 19
Yonkers Riverfest September 19
Sleepy Hollow Street Fair September 20
History Tour @ Untermyer Gardens (Yonkers) September 20
JazzFest White Plains September 23-27
Fall Classic Mansion Tour @ Lyndhurst (Tarrytown) September 24-November 1
Westchester Comedy Club @ Rye Bar & Grill (Rye) September 24
Jazz Concert Series: The American Popular Song Book @ Manhattanville University's Reid Castle (Purchase) September 24
Myths & Mysteries of The Octagon House (Irvington) September 25-November 2
Vic DiBitetto @ Paramount Hudson Valley Theater (Peekskill) September 26
Armonk Outdoor Art Show September 26-27
Death by Chocolate Tea & Tour @ Lyndhurst (Tarrytown) September 27
The Masquerade of the Red Death @ Lyndhurst (Tarrytown) October 2
“Tis the Wind and Nothing More” Immersive Tour @ Octagon House (Irvington) October 2-11
Rosen House Concert Series @ Caramoor (Katonah) October 2-May 14, 2027
Twilight Village @ Philipsburg Manor (Sleepy Hollow) October 2-31
The Headless Horseman Files: An Immersive Sleepy Hollow Whodunit @ Philipsburg Manor (Sleepy Hollow) October 2-31
The Spirits of Sleepy Hollow Country @ Philipsburg Manor (Sleepy Hollow) October 2-31
Irving's Legend @ Washington Irving's Sunnyside (Irvington) October 2-31
Ghost Tours of the Music Hall @ The Tarrytown Music Hall (Tarrytown) October 3-18
An Audience with Poe @ Historic Hudson Valley’s Library (Sleepy Hollow) October 3-31
Westchester Soccer Club Game @ Stadium at Memorial Field (Mount Vernon) October 3
Sleepy Hollow Music Festival @ Kingsland Point Park (Sleepy Hollow) October 3
Bicycle Sundays @ Bronx River Parkway October 4
Westchester Soccer Club Game @ Stadium at Memorial Field (Mount Vernon) October 10
SUP Witches of Sleepy Hollow @ Kingsland Point Park October 10
The Masque of the Red Death @ Lyndhurst (Tarrytown) October 15-30
ArtsFest @ New Rochelle October 15-18
The Lady in White Immersive Ghost Story @ Octagon House (Irvington) October 16-November 1
Hispanic Heritage Month Featured Artist: Breana Ferreira @ Clay Art Center (Port Chester) Through October 17
Westchester Soccer Club Game @ Stadium at Memorial Field (Mount Vernon) October 17
Trick-or-Treat Weekend @ Lyndhurst (Tarrytown) October 17-18
Intermittent Islands: Four Caribbean Women Artists Exhibit @ Katonah Museum of Art (Katonah) October 18-January 24, 2027
Westchester Comedy Club @ Rye Bar & Grill (Rye) October 22
Gothic Market Weekend @ Lyndhurst (Tarrytown) October 23-25
History Tour @ Untermyer Gardens (Yonkers) October 25
Dark Shadows Halloween & Roam on Your Own @ Lyndhurst (Tarrytown) October 31
Fall Classic Mansion Tour @ Lyndhurst (Tarrytown) Through November 1
Autumn Glow Festival @ Glen Island Park (New Rochelle) Through November 1
Myths & Mysteries of The Octagon House (Irvington) Through November 2
The Great Jack O’Lantern Blaze @ Van Cortlandt Manor (Croton-on-Hudson) Through November 8
Legendary Tours @ Washington Irving's Sunnyside (Irvington) Through November 8
The Lady in White Immersive Ghost Story @ Octagon House (Irvington) Through November 1
Hudson Valley Restaurant Week November 2-16
The 2nd Annual Westchester Book Festival @ Katonah November 7
The Dirty Dozen Brass Band @ Paramount Hudson Valley (Peekskill) November 13
50th Anniversary Performances of Annie @ Yorktown Stage (Yorktown) November 14-29
Intermittent Islands: Four Caribbean Women Artists Exhibit @ Katonah Museum of Art (Katonah) Through January 24, 2027
Rosen House Concert Series @ Caramoor (Katonah) Through May 14, 2027
Handmade for the Holidays Market @ Clay Art Center (Port Chester) November
Victorian Christmas @ Octagon House (Irvington) November
Westchester Knicks Home Opener Game @ Westchester County Center (White Plains) November
Lumina: A Magical Light Experience @ Harvest Moon (North Salem) November
The Great Holiday Train Show (Chappaqua) November
Winter Wonderland @ Kensico Dam (Valhalla) November
Glenview Holiday Tour @ Hudson River Museum (Yonkers) November
Holiday Market (New Rochelle) November
