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  • Victorian Christmas at The Octagon House

    Victorian Christmas at The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    19th Century Holiday Cheer Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and …

    $34
  • 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, …

    $20
  • 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 176-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 …

    $30
  • 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, …

    $20
  • Fall Theater at Lyndhurst: Travels with My Aunt

    Lyndhurst Fall Theater
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    M&M Performing Arts presents Travels with My Aunt by Giles Havergal adapted from the Graham Greene novel he wrote, “just for the fun of it.” Don’t miss an enormously appealing, raucously funny comedy that covers espionage, art smuggling, mistaken identity and shady dealings. Winner of the Olivier Award for Best Entertainment in London and Lucille …

    $49
  • Fall Theater at Lyndhurst: Travels with My Aunt

    Lyndhurst Fall Theater
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    M&M Performing Arts presents Travels with My Aunt by Giles Havergal adapted from the Graham Greene novel he wrote, “just for the fun of it.” Don’t miss an enormously appealing, raucously funny comedy that covers espionage, art smuggling, mistaken identity and shady dealings. Winner of the Olivier Award for Best Entertainment in London and Lucille …

    $49
  • Victorian Christmas at The Octagon House

    Victorian Christmas at The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    19th Century Holiday Cheer Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and …

    $34
  • Tarrytown Music Hall Holiday Market

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

    Get into the holiday spirit at Tarrytown Music Hall's annual Holiday Market! This year, the music hall is expanding the Holiday Market to two days, with a new lineup of talented vendors each day. You'll find one-of-a-kind, handcrafted treasures from a curated selection of talented artisans from the Tri-State area. Whether you’re searching for the …

    Free
  • Tarrytown Music Hall Holiday Market

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

    Get into the holiday spirit at Tarrytown Music Hall's annual Holiday Market! This year, the music hall is expanding the Holiday Market to two days, with a new lineup of talented vendors each day. You'll find one-of-a-kind, handcrafted treasures from a curated selection of talented artisans from the Tri-State area. Whether you’re searching for the …

    Free
  • Victorian Christmas at The Octagon House

    Victorian Christmas at The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    19th Century Holiday Cheer Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and …

    $34
  • Octagon House Tour: The Spirit of Christmas Past

    Octagon House Tour: The Spirit of Christmas Past
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    Immersive Octagon House Tour with Readings from 'A Christmas Carol' Join the ladies of The Octagon House amid exquisite holiday decorations as they prepare for their Christmas festivities. After adding ornaments to the tree, checking the table settings, and practicing their carols, visitors will be treated to a performance of the Fezziwig party scene from …

    $58
  • Ghosts of Christmas Past – December Tours of the Tarrytown Music Hall

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

    Created and led by Jonathan Kruk, Hudson Valley Master Storyteller with the guide "Scarlett O' Horror." A spirited tour of the venerable Tarrytown Music Hall's Christmas Ghosts, mixing history and hauntedness during the holidays! ~ Get stories of the Gentlemen Room dancer who made "too merry," becoming the ghostly "Mister Cue." ~ Listen to the …

    $29
  • Ghosts of Christmas Past – December Tours of the Tarrytown Music Hall

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

    Created and led by Jonathan Kruk, Hudson Valley Master Storyteller with the guide "Scarlett O' Horror." A spirited tour of the venerable Tarrytown Music Hall's Christmas Ghosts, mixing history and hauntedness during the holidays! ~ Get stories of the Gentlemen Room dancer who made "too merry," becoming the ghostly "Mister Cue." ~ Listen to the …

    $29
  • Victorian Christmas at The Octagon House

    Victorian Christmas at The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    19th Century Holiday Cheer Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and …

    $34
  • Octagon House Tour: The Spirit of Christmas Past

    Octagon House Tour: The Spirit of Christmas Past
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    Immersive Octagon House Tour with Readings from 'A Christmas Carol' Join the ladies of The Octagon House amid exquisite holiday decorations as they prepare for their Christmas festivities. After adding ornaments to the tree, checking the table settings, and practicing their carols, visitors will be treated to a performance of the Fezziwig party scene from …

    $58
  • Judy Collins – Holiday & Hits

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

    Judy Collins has long inspired audiences with sublime vocals, boldly vulnerable songwriting, personal life triumphs, and a firm commitment to social activism. In the 1960s, she evoked both the idealism and steely determination of a generation united against social and environmental injustices. Five decades later, her luminescent presence shines brightly as new generations bask in …

    $47.50 – $77.50
  • Victorian Holiday Tea and Tour

    Victorian Holiday Tea and Tour
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    The event will begin with a tour of Lyndhurst Mansion. This one-hour tour covers two floors and gives visitors a rare glimpse of the lavish decorative arts and furniture left at Lyndhurst by previous owners. The mansion will be spectacularly decorated for the Holidays! The tour visits approximately 16 rooms and involves climbing one staircase …

    $85
  • Victorian Christmas at The Octagon House

    Victorian Christmas at The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    19th Century Holiday Cheer Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and …

    $34
  • Paper Snowflake Making Class

    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Take your snowflake-making to the next level in this hands-on workshop. Participants will move beyond basic folds and cuts to explore intricate seasonal designs. Recommended for ages 12+.

    Free – $10
  • Victorian Holiday Tea and Tour

    Victorian Holiday Tea and Tour
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    The event will begin with a tour of Lyndhurst Mansion. This one-hour tour covers two floors and gives visitors a rare glimpse of the lavish decorative arts and furniture left at Lyndhurst by previous owners. The mansion will be spectacularly decorated for the Holidays! The tour visits approximately 16 rooms and involves climbing one staircase …

    $85
  • Tarrytown Tree Lighting and Holiday Festivities

    Patriots Park Patriots Park, Tarrytown, NY, United States

    Patriots Park in Tarrytown comes alive on December 6 with the village’s annual Holiday Kickoff, a cozy, family-friendly celebration that blends the charm of the season with the community’s creative spirit. From 2 to 4 pm, children can enjoy a cheerful Santa meet-and-greet while families take part in hands-on Hanukkah crafts—an inviting mix of traditions. …

    Free
  • Octagon House Tour: The Spirit of Christmas Past

    Octagon House Tour: The Spirit of Christmas Past
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    Immersive Octagon House Tour with Readings from 'A Christmas Carol' Join the ladies of The Octagon House amid exquisite holiday decorations as they prepare for their Christmas festivities. After adding ornaments to the tree, checking the table settings, and practicing their carols, visitors will be treated to a performance of the Fezziwig party scene from …

    $58
  • Christ Church Christmas Concert and Holiday Market

    Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

    Annual Christmas Concert and Holiday Market. Enjoy performances by the Choir of Christ Church San Marcos and other musical performers! Feast on bake sale items and shop the gift sale. Doors open at 2 pm for the holiday market. Washington Irving, author of “The Legend of Sleepy Hollow,” followed the Rev. Dr. William Creighton to …

    Free
  • Sparkle & Swing: A Christmas Concert

    Irvington Theater Performances
    Irvington Theater 85 Main Street, Irvington, NY, United States

    The Hudson Valley Singers is a beloved Westchester institution, performing beautiful choral music in the region for 74 years. We’re thrilled to welcome them to our stage as they present Sparkle & Swing: A Christmas Concert. Celebrate the holidays with a joyful blend of traditional, jazz and popular favorites performed by full chorus, stellar soloists …

    $10 – $45

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.