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  • Ann Hampton Callaway • Fever! The Peggy Lee Century

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

    Tony nominee Ann Hampton Callaway, one of the leading pop/jazz singers of our time, has created an exciting night of songs and stories in celebration of her inspiration and one of America’s most beloved artists, Peggy Lee. On the heels of Ann's Streisand Songbook symphonic triumph, this show celebrates the 100th birthday of the trailblazing …

    $30 – $35
  • Canceled Irvington Farmers Market

    Main Street School 101 Main Street, Irvington, NY, United States

    Enjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh local produce, seafood and meats, cheese, pickles, prepared foods and baked goods. Sundays, 9 am to 1:30 pm rain or shine. Well behaved dogs are …

    Free
  • History of Rockwood Hall

    History of Rockwood Hall
    Rockwood Hall Phelps Way, Pleasantville, NY, United States

    Join Rockwood docent David Teich on an adventure into the past as he explores Rockwood Hall and its rich history through stories of the land and the people who called it home. Former estate of William Rockefeller, this site boasts scenic views overlooking the Hudson, lush forests, and remnants of 19th century luxuries. Leashed dogs …

    $3
  • 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
  • John Lang Nonet • Earotica

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

    John Lang Nonet features Brandon Lee on trumpet, Mark Patterson on trombone, Mark Lopeman on alto sax, Nick Hempton on tenor sax, Saul Dautch on bari sax, Roberta Piket on piano, Pete McCann on guitar, Peter Retzlaff on drums and John Lang on bass! Distinguished bassist, leader and arranger John Lang directs this crack contingent …

    $15 – $20
  • John Lang Nonet • Earotica

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

    John Lang Nonet features Brandon Lee on trumpet, Mark Patterson on trombone, Mark Lopeman on alto sax, Nick Hempton on tenor sax, Saul Dautch on bari sax, Roberta Piket on piano, Pete McCann on guitar, Peter Retzlaff on drums and John Lang on bass! Distinguished bassist, leader and arranger John Lang directs this crack contingent …

    $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
  • 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
  • Sunset Jazz at Lyndhurst

    Sunset Jazz at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Enjoy eight free Thursday evenings of Jazz at Tarrytown's Lyndhurst mansion while watching the sun set over the Hudson River. Picnicking is encouraged! Lyndhurst has also partnered with local caterer Geordane's for preordered food and to-snacks during each show. Wine will be available to purchase ahead of time from  MySherry &more Inc ONLY alongside the purchase …

    Free
  • 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
  • Jazz at Pierson Park

    Jazz at Pierson Park
    Pierson Park 238 West Main Street, Tarrytown, NY, United States

    Enjoy eight free Friday evenings of Jazz at Tarrytown's waterfront Pierson Park. Bring a picnic dinner or enjoy local food truck fare while watching the sun set over the Hudson River. 2022 Schedule: Fridays, July 8 through August 26. July 8: Yaacov Mayman - Organ Quartet July 15 – Sheryl Bailey & The SBQ July …

    Free
  • 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
  • Rufus Reid and Expedition

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

    Rufus Reid and Expedition featuring Rufus Reid on bass, Roxy Coss on saxophones, Michael Rodriguez on trumpet, Roberta Piket on piano and Kenneth Salters on drums! He calls himself “The Evolving Bassist,” and for the world-class musician, composer and educator Rufus Reid, there may be no better nickname. In addition to leading his own groups …

    $25 – $30
  • Rufus Reid and Expedition

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

    Rufus Reid and Expedition featuring Rufus Reid on bass, Roxy Coss on saxophones, Michael Rodriguez on trumpet, Roberta Piket on piano and Kenneth Salters on drums! He calls himself “The Evolving Bassist,” and for the world-class musician, composer and educator Rufus Reid, there may be no better nickname. In addition to leading his own groups …

    $25 – $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.