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  • Autumn Tree Identification Walk

    Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United States

    Join naturalist John McShane for a stroll through the Rockefeller State Park Preserve and discuss some key skills on how to identify native trees. You’ll also learn how and why the leaves change color in the fall. The hike will be around 1-2 miles with frequent stops for discussion. Suggested ages 10+. Meet in the …

    $3
  • Sleepy Hollow Halloween 10K

    Morse School 30 Pocantico Street, Sleepy Hollow, NY, United States

    Enjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery and the Old Dutch Church. You never know what might be lurking on the course in Sleepy Hollow… Registration is limited, costumes encouraged but not …

    $40 – $50
  • Lyndhurst Spirited Mansion Weekend

    Lyndhurst Spirited Mansion Weekend
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Lyndhurst will be open Halloween Weekend with an “Explore at Your Own Pace” event--Spirited Mansion Weekend. Visitors can walk through the mansion without a guided tour, view the seasonal decorations at their own pace, and take in the wonders of the historic mansion. You will see the majestic vestibule and entrance hall, reception room, parlor, …

    $16 – $24
  • Victorian Photography Studio

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    New for this Halloween season is the chance to bring home a piece of photographic history. Victorian Photography Studio from Gettysburg, Pennsylvania will be at the Lyndhurst mansion ready to take your portrait using 19th-century photographic technology, resulting in a one-of-a-kind tintype portrait. Bring home a special memento of your trip to the gothic mansion during …

    $50 – $80
  • Home of the ‘Legend’

    Home of the ‘Legend’
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    At this family-friendly happening, visitors can tour Washington Irving’s house—decorated for the season—watch an original shadow puppet short film, and enjoy games on the lawn. A special exhibit highlights how "The Legend of Sleepy Hollow" has lived in the imagination of popular culture through the centuries since its publication.

    Free – $12
  • Kykuit Tours

    Kykuit Tours
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Built between 1906 and 1913, Kykuit was home to four generations of the Rockefeller family. In 2022 the site will be open for guided tours Saturday-Sunday from May 21-October 2; and Wednesday-Monday between October 5-November 13. There are three distinct Kykuit tours available: Classic Tour: Great for first-time visitors. Your visit will include the main floor of …

    $18 – $60
  • Philipsburg Manor Tours

    Philipsburg Manor Tours
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Journey to Colonial America! Wander along a woodland path and enter the year 1750, when Philipsburg Manor was a thriving milling and trading complex that was home to several hundred tenant farmers and twenty three enslaved individuals of African descent. Step into the gristmill and learn about the work of Caesar, the enslaved African miller. Tour …

    $12 – $17
  • Union Church Tours

    Union Church Tours
    Union Church of Pocantico Hills 555 Bedford Road, Sleepy Hollow, NY, United States

    The Union Church of Pocantico Hills is a repository of awe-inspiring art by Matisse & Chagall. Stained-glass windows by European masters, commissioned by the Rockefeller family, adorn this unassuming country church. Henri Matisse’s last work, the Rose Window, and nine windows by Marc Chagall create a dramatic combination of light and color, art and spirituality. …

    $9
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of "The Legend of Sleepy Hollow", which recently celebrated its Bicentennial. Best of all, …

    $15
  • Octagon House Myths and Mysteries Tour

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    18 miles north of New York City, high on a bank along The Hudson River sits The Armour-Stiner (Octagon) House. Built in 1860, this enigmatic, eight-sided, domed landmark is the pride of the Village of Irvington, in the heart of “Sleepy Hollow Country.” During the month of October, The Octagon House is pleased to announce …

    $29
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about Washington Irving, his impact on American Literature and the enduring appeal of "The Legend of Sleepy Hollow", which recently celebrated its Bicentennial. Best of all, …

    $15
  • Classic Daytime Cemetery Tour

    Classic Daytime Cemetery Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    Soak up the beauty of this 173-year old cemetery while your guide regales you with stories of the fascinating people resting here in peace. This two-hour daytime walk is the perfect way "to have a colloquy among the tombs" as Washington Irving, famous author of "The Legend of Sleepy Hollow", did himself back in 1849. You'll …

    $25
  • Octagon House “The Lady in White” Interactive Tour & Performance

    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    Her ship went down in flames, but the Lady in White returned to the Octagon House and still waits for her lover to find her there. Based on the 1956 Carl Carmer tale, your visit with The Spirit of the Octagon House will take you through the rooms of this unique to the world home …

    $39
  • Halloween Block Party

    Headless Horseman Statue 362 North Broadway, Sleepy Hollow, NY, United States

    Halloween in Sleepy Hollow is a month-long celebration, and if you visit the last two weekends of October you know how we like a good block party! From 4 pm to 9:30 pm this Saturday, the lawn around the Headless Horseman Statue hosts local DJ Mac 11, food trucks and storytelling for the whole family!

    Free
  • Halloween Beekman Block Party

    Bring your best costume to downtown Sleepy Hollow and dance the night away! Music by Studio 100, DJ Anthony Veras, and DJ RaySTAR. Special appearance by Flame. Food and beverage vendors, prizes for best costume!

    Free
  • Hulda’s Night at Rockefeller State Park Preserve

    Hulda’s Night at Rockefeller State Park Preserve
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    Hulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! You walk through the gathering gloom, your path lit only by lanterns. The dark woods surround you as the chill night air settles in. Your group joins …

    $28
  • Lyndhurst After Dark!

    Lyndhurst After Dark!
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    You’ve experienced the splendor of the Lyndhurst Mansion during the day, but have you seen it draped in candlelight? This Halloween Season, experience the history of the Mansion and explore Victorian lore in the glow of an October evening: Lyndhurst After Dark! Timed entry allows visitors to take a semi-guided walk through the Mansion as it …

    $20 – $26
  • The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns—all designed and hand-carved on site by a team of talented artisans. New for 2022, watch the animated “Jack” Smith Shop …

    $24 – $99
  • Murder and Mayhem Walking Tour

    Murder and Mayhem Walking Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    The true stories on this two-hour lantern tour are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his father before turning the …

    $45
  • Irving’s Legend at Sunnyside

    Irving’s Legend at Sunnyside
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    Irving’s Legend returns reimagined this fall. Performed under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk will cast a spell with dramatic performances of the classic tale. Live music and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages! Advance reservations are required. No tickets will …

    $30 – $70
  • Hulda’s Night at Rockefeller State Park Preserve

    Hulda’s Night at Rockefeller State Park Preserve
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    Hulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! You walk through the gathering gloom, your path lit only by lanterns. The dark woods surround you as the chill night air settles in. Your group joins …

    $28
  • Sleepy Hollow Cemetery Lantern Tour

    Sleepy Hollow Cemetery Lantern Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Soak up the history of this famous cemetery by the light of kerosene lanterns! It’s like stepping back in time as you visit some of the most impressive residents, including William Rockefeller, Andrew Carnegie, John Dustin Archbold and others resting in peace in the cemetery's north end. As this is only a one-hour tour, you’ll …

    $45
  • American Aristocrats Cemetery Tour

    American Aristocrats Cemetery Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Short on time? Make the most of it and meet the crème de la crème on this one-hour lantern tour of Sleepy Hollow Cemetery! The Gilded Age began after the Civil War and ended around 1900. It was a time of tremendous industrialization and rapid economic growth. Railroads were built to connect the East Coast …

    $30
  • American Aristocrats Cemetery Tour

    American Aristocrats Cemetery Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Short on time? Make the most of it and meet the crème de la crème on this one-hour lantern tour of Sleepy Hollow Cemetery! The Gilded Age began after the Civil War and ended around 1900. It was a time of tremendous industrialization and rapid economic growth. Railroads were built to connect the East Coast …

    $30

There's something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.