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  • 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
  • Tunes & Tinis: Piano Bar with Nina Zeitlin

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    Dust off your vocal chords—time to sing, lounge, sip, and nibble! Grab your friends and your request list and get ready to sing with Nina, a Brooklyn-based award-winning singer, voice actor, songwriter, producer, and piano entertainer! Whether you’re singing along to an old favorite or brave enough to grab the mic for a solo performance, this …

    $20 – $25
  • Leslie Odom Jr. – The Christmas Tour

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

    Leslie Odom, Jr. is a Tony and Grammy Award-winning, three-time Emmy and two-time Academy Award-nominated songwriter, actor, and a New York Times bestselling author.Well known for his breakout role as ‘Aaron Burr’ in thePulitzer Prize- winning Broadway musical Hamilton, Odom is set to make a highly anticipated return to his award-winning role on September 9 …

    $95.50 – $155.50
  • 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 Laurie Berkner Band: A Live Holiday Concert

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

    Presented by Metropolitan Entertainment AM Show: Door: 10 AM Show: 11 AM PM Show: Door: 2 PM Show: 3 PM VIP tickets include a meet and greet and photo op. Babies under age one seated in laps are free and will be given a comp ticket at box office.

    $44 – $109
  • The Laurie Berkner Band: A Live Holiday Concert

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

    Presented by Metropolitan Entertainment AM Show: Door: 10 AM Show: 11 AM PM Show: Door: 2 PM Show: 3 PM VIP tickets include a meet and greet and photo op. Babies under age one seated in laps are free and will be given a comp ticket at box office.

    $44 – $109
  • 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
  • Everett Bradley’s HOLIDELIC with Special Guest Meredith Vieira

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

    For the first time at Irvington Theater, HOLIDELIC is coming to town! Created by Grammy-nominated singer/percussionist Everett Bradley (Bon Jovi, Bruce Springsteen and the E Street Band, Hall & Oates, and more), HOLIDELIC is funk-lore cleverly told through 70’s and 80’s inspired originals and reimagined classics that celebrate diversity and love as one nation under …

    $38 – $48
  • 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
  • Film Series: The Polar Express

    Classic Films in a Classic Venue
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Classic films in a classic venue. On Christmas Eve, a young boy embarks on a magical adventure to the North Pole on the Polar Express, while learning about friendship, bravery, and the spirit of Christmas. Runtime: 100 Minutes Directed by Robert Zemeckis Starring Tom Hanks and Chris Coppola

    $11
  • 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
  • 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

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.