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  • Melissa Etheridge – One Way Out Tour

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

    Melissa Etheridge stormed onto the American rock scene in 1988 with the release of her critically acclaimed self-titled debut album, which led to an appearance on the 1989 Grammy Awards show. For several years, her popularity grew around such memorable originals as "Bring Me Some Water," "No Souvenirs" and "Ain't It Heavy," for which she …

    $68 – $148
  • 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
  • Full Moon Hike: “Super Strawberry Moon”

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

    Experience Rockefeller State Park Preserve after dark and observe the “super” moon as it approaches perigee (when it’s closest to Earth) and therefore appears unusually large and bright! Join this 4-mile hike on carriage roads lit by moonlight. You will walk at a brisk pace; some hiking experience is recommended. Meet in the Rockefeller State …

    $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
  • Local Lore and Legends

    Local Lore and Legends
    Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United States

    While Sleepy Hollow is well known for its headless horseman, there are quite a few lesser-known legends that take place on this land. The names of some of our most iconic locations such as Spook Rock, Ravens Rock, Witch’s Spring come from stories that have been told by locals dating back hundreds of years. Join …

    $4
  • 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
  • Monty Alexander Trio

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

    Don't miss the legendary jazz pianist Monty Alexander perform at Tarrytown's Jazz Forum! Fifty-five years after he moved to the United States from Kingston, Jamaica, his home town, Monty Alexander is an American classic, touring the world relentlessly with various projects, delighting a global audience drawn to his vibrant personality and soulful message. His spirited …

    $30 – $35
  • The Zappa Band: Featuring Frank Zappa Alumni

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

    Frank Zappa alumni play Frank Zappa’s music live! The Zappa Band is Mike Keneally (1987-1988), Ray White (1976-1984), Robert Martin (1981-1988) and Scott Thunes (1981-1988). Each musician played in the studio and on the road with Zappa during his career. Three of these alums played on ZAPPA 88: The Last U.S. Show, one of the …

    $38 – $58
  • Monty Alexander Trio

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

    Don't miss the legendary jazz pianist Monty Alexander perform at Tarrytown's Jazz Forum! Fifty-five years after he moved to the United States from Kingston, Jamaica, his home town, Monty Alexander is an American classic, touring the world relentlessly with various projects, delighting a global audience drawn to his vibrant personality and soulful message. His spirited …

    $30 – $35
  • Monty Alexander Trio

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

    Don't miss the legendary jazz pianist Monty Alexander perform at Tarrytown's Jazz Forum! Fifty-five years after he moved to the United States from Kingston, Jamaica, his home town, Monty Alexander is an American classic, touring the world relentlessly with various projects, delighting a global audience drawn to his vibrant personality and soulful message. His spirited …

    $30 – $35
  • Westminster Kennel Club: Masters Agility Championship

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Agility is a timed competition that tests a dog’s ability to complete an obstacle course following the commands of its handler. Purebred and All-American (mixed breed) dogs are eligible, to compete in 1 of 5 height classes and are judged on time and completion (minus faults) of the course. Tickets and Parking: Starting May 16, …

    $12.5 – $30
  • TaSH Farmers Market

    Tarrytown and Sleepy Hollow Farmers Market
    Patriots Park Patriots Park, Tarrytown, NY, United States

    Fresh Hudson Valley produce, meat, bread, honey, specialty foods, cut flowers, dairy products, beer and wine. There is live music and sometimes demonstrations of traditional crafts. Route 9 (Broadway) next to the Warner Library. Free parking across the street at John Paulding School. Saturdays, 8:30 am to 1:30 pm rain or shine. Well behaved dogs …

    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
  • 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
  • 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
  • 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
  • Wildflower Walk at Rockefeller State Park

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

    Join botanist Patty Butter for a leisurely walk and learn about the identification of wildflowers in Rockefeller State Park Preserve. Contribute as a citizen scientist to increase the knowledge of the ecology of the Preserve by logging your observations in the iNaturalist app. Bring a camera or cell phone to take pictures and add the …

    $4
  • Tarrytown Dogs on Parade

    Patriots Park Patriots Park, Tarrytown, NY, United States

    The Village of Tarrytown together with the Tarrytown/ Sleepy Hollow Chamber of Commerce and Bark and Meow invite you to join Tarrytown Dogs on Parade. With the 146th Annual Westminster Kennel Club Dog Show coming to town, we want to show off our own lovable pups! Bring your leashed dog to march with the best of …

    Free

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.