Sponsored

  • 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
  • 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
  • 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
  • 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
  • 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
  • Tarryhollow: Heroes and Villains of the Hollow

    Tarryhollow: Heroes and Villains of the Hollow
    Patriots Park Patriots Park, Tarrytown, NY, United States

    Although small in size, the villages of Tarrytown and Sleepy Hollow have been home to larger than life personalities and events that shaped American history. On this two-hour walking tour, you will visit the Captors’ Monument and learn about the three local militiamen who captured British spy Major John André, triggering the discovery of Benedict Arnold’s treason. You will hear …

    $24.99
  • 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
  • Alexander McCabe Quartet

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

    Alexander McCabe is a saxophonist and composer. Originally from Boston, he has been performing in and around New York City since the 1980s. Alexander was a featured soloist with the Ray Charles Orchestra and was an original member, and toured with, the Chico O'Farril Afro-Cuban big band. Alexander McCabe's work can be heard in dozens …

    $15 – $20
  • Alexander McCabe Quartet

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

    Alexander McCabe is a saxophonist and composer. Originally from Boston, he has been performing in and around New York City since the 1980s. Alexander was a featured soloist with the Ray Charles Orchestra and was an original member, and toured with, the Chico O'Farril Afro-Cuban big band. Alexander McCabe's work can be heard in dozens …

    $15 – $20
  • Dionne Warwick

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

    Dionne Warwick is a six-time Grammy Award-winning music legend who has earned more than 75 charted hit songs and sold over 100 millionrecords. She was discovered by Burt Bacharach and Hal David in 1961, and went on to record 18 consecutive Top 100 singles (“Don’t Make Me Over,” Walk on By,” “Say a Little Prayer,” …

    $78 – $118
  • Birding at Rockefeller State Park Preserve

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

    Rockefeller State Park Preserve together with adjoining private lands is one of the largest undeveloped tracts of land in Westchester County. With its mix of woodlands, fields, wetlands and a lake, the Preserve supports a diversity of species, especially birds. Come find out why the National Audubon Society has designated this an Important Bird Area. A hint: nearly …

    Free
  • Historic Irvington & Tarrytown Walking Tour

    Dows Lane 50 Dows Lane, Irvington, NY, United States

    Free, easy loop beginning and ending at Dows Lane in Irvington. Enjoy the mostly level, shaded walk in one of the most storied sections of the Aqueduct. Learn about the remarkable Villa Lewaro, the estate of Madam CJ Walker, the African-American entrepreneur who was America’s first female self-made millionaire. Walk the grounds of Lyndhurst Mansion, …

    Free
  • 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 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
  • 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
  • Sing Sing Prison and the History of Criminal Justice

    The Jug Tavern of Sparta, Inc. 74 Revolutionary Road, Ossining, NY, United States
    Virtual Event

    Join historic Jug Tavern online Tuesday September 13 as Brent D. Glass, Executive Director of Sing Sing Prison Museum, brings you up to date on the progress of the museum in Ossining. Dr. Glass will share an illustrated presentation about one of America’s iconic institutions. Every chapter in the history of criminal justice has a …

    Free
  • 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
  • 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
  • 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 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
  • 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
  • Fall Crafts at Lyndhurst

    Fall Crafts at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Fall Crafts at Lyndhurst returns in 2022 from September 16th through September 18th where you can shop for one-of-a-kind items from 200 craftspeople and makers. Find handmade original fashions, accessories, and jewelry; functional and sculptural works in ceramics, glass, metal, fiber, wood, and mixed media; and fine art painting, printmaking, drawing, and photography. Plus, enjoy …

    $4 – $12

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.