Sponsored

  • 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
  • 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
  • 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 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
  • Benny Benack III Quintet

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

    Making his Jazz Forum Debut! By age 28, trumpeter and singer Benny Benack III has proven to be a rare talent: not only a fiery trumpet player with a stirring command of the postbop trumpet vernacular in the vein of Kenny Dorham and Blue Mitchell, but also a singer with a sly, mature, naturally expressive …

    $25 – $30
  • Henry Rollins – Good to See You 2022

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

    On the Good To See You 2022 tour Henry will faithfully recount the events of his life in the brief pre-COVID period since the last tour and when things got even stranger over the last several months. It's been an interesting time to say the least and he's got some great stories to tell. In …

    $35
  • Reelin’ in the Years – Celebrating the Music of Steely Dan

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

    Reelin’ in the Years celebrates the timeless music of Steely Dan. Comprised of world class touring and recording session musicians that reads like a who’s who in the music industry, including bandleader and drummer Jerry Marotta. Based in Woodstock, NY, Reelin’ have sold out all of the major venues they’ve performed in for the last …

    $30 – $35
  • 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

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.