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  • History in the Landscape Tour – Lyndhurst

    History in the Landscape Tour – Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    This outdoor walking tour examines the history of the landscaped Lyndhurst estate throughout three families’ ownership. Visitors are led down from the Lyndhurst Veranda and its marble garden furniture and fountains through a series of garden sitting areas and rock outcroppings known as “rockeries” which offer sweeping views of the Hudson River. Trees, plantings, and …

    $15 – $20
  • Sunnyside Tours

    Sunnyside Tours
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has been charming guests for generations. Visitors today hear about Washington Irving’s storied past and how he came to be America’s first internationally famous author. His …

    $12 – $17
  • Octagon House Classic Tour

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

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …

    $29
  • 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
  • Old Croton Aqueduct Weir Tour

    Old Croton Aqueduct Weir Tour
    Joseph G. Caputo Community Center 95 Broadway, Ossining, NY, United States

    The Old Croton Aqueduct, New York City's original water supply, runs from, Croton-on-Hudson into the Bronx and Manhattan, passing through Sleepy Hollow and Tarrytown. For most of its length, the Aqueduct is a horseshoe-shaped brick tunnel 8.5 feet high by 7.5 feet wide, set on a stone foundation and protected with an earthen cover and stone …

    Free
  • 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
  • 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
  • Delbert Anderson Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Delbert Anderson is enjoying a music career as one of today's most forward thinking artists. Recording, touring, community outreach, music educational workshops, composing/arranging and guest appearances keep Anderson busy not only in his hometown of Farmington, NM but worldwide. Anderson has been featured on JazzTimes, Grammy.com, NASA, NPR Music Top 10, Smithsonian Magazine, Yahoo/Mic.com, TEDx, …

    $15 – $20
  • Delbert Anderson Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Delbert Anderson is enjoying a music career as one of today's most forward thinking artists. Recording, touring, community outreach, music educational workshops, composing/arranging and guest appearances keep Anderson busy not only in his hometown of Farmington, NM but worldwide. Anderson has been featured on JazzTimes, Grammy.com, NASA, NPR Music Top 10, Smithsonian Magazine, Yahoo/Mic.com, TEDx, …

    $15 – $20
  • Octagon House Classic Tour

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

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …

    $29
  • Octagon House Classic Tour

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

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …

    $29
  • Stargazing in Rockefeller State Park Preserve

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

    Experience Sleepy Hollow after dark! Peer into the cosmos with Vinny Coulehan of the Rockland Astronomy Club; view the night sky through a telescope and catch a glimpse of our planetary neighbors. Meet at the Rockefeller State Park Visitor’s Center courtyard, followed by a short walk on the Overlook trail to the viewing location. Dress …

    $3
  • Stargazing in Rockefeller State Park Preserve

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

    Experience Sleepy Hollow after dark! Peer into the cosmos with Vinny Coulehan of the Rockland Astronomy Club; view the night sky through a telescope and catch a glimpse of our planetary neighbors. Meet at the Rockefeller State Park Visitor’s Center courtyard, followed by a short walk on the Overlook trail to the viewing location. Dress …

    $3
  • History in the Landscape Tour – Lyndhurst

    History in the Landscape Tour – Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    This outdoor walking tour examines the history of the landscaped Lyndhurst estate throughout three families’ ownership. Visitors are led down from the Lyndhurst Veranda and its marble garden furniture and fountains through a series of garden sitting areas and rock outcroppings known as “rockeries” which offer sweeping views of the Hudson River. Trees, plantings, and …

    $15 – $20
  • Sunnyside Tours

    Sunnyside Tours
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    A charming, romantic Hudson River landscape. America’s “Founding Father of Literature” created a romantic, picturesque estate nestled along the Hudson riverbank. The enchanted landscape of Washington Irving’s much-loved Sunnyside has been charming guests for generations. Visitors today hear about Washington Irving’s storied past and how he came to be America’s first internationally famous author. His …

    $12 – $17
  • Octagon House Classic Tour

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

    The Armour-Stiner Octagon House, a registered National Historic Landmark, was created as a summer retreat by tea-importer Joseph Stiner. Its shape was based on the theories of Orson Squire Fowler, a phrenologist, who believed octagonal houses enclosed more space, allowed the sun in at all times, and permitted more views into the landscape. The tour …

    $29
  • 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
  • John Pizzarelli Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Fresh off his Grammy-winning standards collaboration with James Taylor, the world-renowned guitarist and singer John Pizzarelli recently released the first solo guitar album of his masterful four-decade career, a tribute to Pat Metheny. Learning Metheny’s wonderful compositions helped John through the grieving process of losing his parents – the legendary guitarist Bucky Pizzarelli and Ruth …

    $35 – $40
  • Shakespeare at Sunset

    Shakespeare at Sunset
    Rockwood Hall Phelps Way, Pleasantville, NY, United States

    As William Shakespeare famously wrote, "All the world's a stage." Bring a picnic and a blanket and come ready to read or just relax and listen. We will have fun with the Bard's work as it was meant to be experienced: outdoors and out loud, without homework, essays, or tests. Whether you're a novice, a …

    $3
  • Buddy Guy

    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    The title of Buddy Guy's latest album says it all: The Blues Is Alive and Well. The legendary blues artist's eighteenth solo LP and follow-up to 2015's Born to Play Guitar showcases his raw and unadulterated sound, its fifteen tracks a true pleasure for aficionados and genre newcomers alike. "I got children and grandchildren who …

    $78 – $148
  • John Pizzarelli Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Fresh off his Grammy-winning standards collaboration with James Taylor, the world-renowned guitarist and singer John Pizzarelli recently released the first solo guitar album of his masterful four-decade career, a tribute to Pat Metheny. Learning Metheny’s wonderful compositions helped John through the grieving process of losing his parents – the legendary guitarist Bucky Pizzarelli and Ruth …

    $35 – $40
  • John Pizzarelli Trio

    Jazz Forum Club Performances
    Jazz Forum Club 1 Dixon Lane, Tarrytown, NY, United States

    Fresh off his Grammy-winning standards collaboration with James Taylor, the world-renowned guitarist and singer John Pizzarelli recently released the first solo guitar album of his masterful four-decade career, a tribute to Pat Metheny. Learning Metheny’s wonderful compositions helped John through the grieving process of losing his parents – the legendary guitarist Bucky Pizzarelli and Ruth …

    $35 – $40

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.