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Visit Sleepy Hollow

Where the Legend Lives

  • See
    • Armour-Stiner Octagon House
    • Christ Episcopal Church
    • David Rockefeller Creative Arts Center at Pocantico
    • Headless Horseman Bridge
    • Headless Horseman Statue
    • Historical Society
    • Kykuit
    • Legend Landmarks
    • Lyndhurst
      • A Dark Shadows Halloween at Lyndhurst Mansion
      • Gothic Market Weekend at Lyndhurst
      • The Masquerade of the Red Death
      • Trick-or-Treat Weekend at Lyndhurst
    • Old Croton Aqueduct Trail
    • Old Dutch Church
    • Philipsburg Manor
      • The Headless Horseman Files
      • The Spirits of Sleepy Hollow Country
      • Twilight Village at Sleepy Hollow
    • Rockefeller State Park Preserve 
      • The Legend of Sleepy Hollow and Local Lore
      • Rocky’s 5K
    • Sleepy Hollow Cemetery
      • Sleepy Hollow Cemetery Tours
      • Sleepy Hollow Cemetery Special Events
    • Sleepy Hollow Lighthouse
    • Stone Barns Center
    • Sunnyside
      • Irving’s Legend
    • Union Church of Pocantico Hills
  • Events
    • Events
    • A Perfect Fall Day in Sleepy Hollow
    • Halloween in Sleepy Hollow Country
    • An Audience with Poe
    • A Dark Shadows Halloween at Lyndhurst Mansion
    • General Daniel Delavan & the American Revolution
    • Great Jack O’Lantern Blaze
    • The Headless Horseman Files
    • Irving’s Legend
    • Jazz Forum
    • The Legend of Sleepy Hollow and Local Lore
    • Sleepy Hollow Cemetery Tours
    • Sleepy Hollow Cemetery Special Events
    • Sleepy Hollow Haunted Hayride
    • Sleepy Hollow Music Festival
    • Sleepy Hollow Street Fair
    • The Spirits of Sleepy Hollow Country
    • SUP Witches Festival
    • Tarrytown Music Hall Performances
    • Tarrytown Music Hall Ghost Tours
    • Twilight Village at Sleepy Hollow
  • Eat
    • Breakfast
    • Lunch and Dinner
    • Sweets
    • Drinks
  • Shop
    • Apple Picking
    • Christ Church/San Marcos Annual Fall Fair
    • Farmers Markets
    • The Goblin Market
    • Sleepy Hollow Souvenirs
    • Warner Library Book Sale
  • Stay
    • Hotels
    • Motels and Budget
    • Inns and Bed & Breakfasts
    • Camping
  • About
    • Sleepy Hollow Beyond October: A Spring and Summer Guide
    • Sleepy Hollow Without a Car: Visiting by Train
    • A Perfect Fall Day in Sleepy Hollow
    • The Other Ghosts of Sleepy Hollow
    • Sleepy Hollow Country
    • How Charles Dickens Stole Christmas
    • Movies Made Here
    • Directions
  • See
    • Armour-Stiner Octagon House
    • Christ Episcopal Church
    • David Rockefeller Creative Arts Center at Pocantico
    • Headless Horseman Bridge
    • Headless Horseman Statue
    • Historical Society
    • Kykuit
    • Legend Landmarks
    • Lyndhurst
      • A Dark Shadows Halloween at Lyndhurst Mansion
      • Gothic Market Weekend at Lyndhurst
      • The Masquerade of the Red Death
      • Trick-or-Treat Weekend at Lyndhurst
    • Old Croton Aqueduct Trail
    • Old Dutch Church
    • Philipsburg Manor
      • The Headless Horseman Files
      • The Spirits of Sleepy Hollow Country
      • Twilight Village at Sleepy Hollow
    • Rockefeller State Park Preserve 
      • The Legend of Sleepy Hollow and Local Lore
      • Rocky’s 5K
    • Sleepy Hollow Cemetery
      • Sleepy Hollow Cemetery Tours
      • Sleepy Hollow Cemetery Special Events
    • Sleepy Hollow Lighthouse
    • Stone Barns Center
    • Sunnyside
      • Irving’s Legend
    • Union Church of Pocantico Hills
  • Events
    • Events
    • A Perfect Fall Day in Sleepy Hollow
    • Halloween in Sleepy Hollow Country
    • An Audience with Poe
    • A Dark Shadows Halloween at Lyndhurst Mansion
    • General Daniel Delavan & the American Revolution
    • Great Jack O’Lantern Blaze
    • The Headless Horseman Files
    • Irving’s Legend
    • Jazz Forum
    • The Legend of Sleepy Hollow and Local Lore
    • Sleepy Hollow Cemetery Tours
    • Sleepy Hollow Cemetery Special Events
    • Sleepy Hollow Haunted Hayride
    • Sleepy Hollow Music Festival
    • Sleepy Hollow Street Fair
    • The Spirits of Sleepy Hollow Country
    • SUP Witches Festival
    • Tarrytown Music Hall Performances
    • Tarrytown Music Hall Ghost Tours
    • Twilight Village at Sleepy Hollow
  • Eat
    • Breakfast
    • Lunch and Dinner
    • Sweets
    • Drinks
  • Shop
    • Apple Picking
    • Christ Church/San Marcos Annual Fall Fair
    • Farmers Markets
    • The Goblin Market
    • Sleepy Hollow Souvenirs
    • Warner Library Book Sale
  • Stay
    • Hotels
    • Motels and Budget
    • Inns and Bed & Breakfasts
    • Camping
  • About
    • Sleepy Hollow Beyond October: A Spring and Summer Guide
    • Sleepy Hollow Without a Car: Visiting by Train
    • A Perfect Fall Day in Sleepy Hollow
    • The Other Ghosts of Sleepy Hollow
    • Sleepy Hollow Country
    • How Charles Dickens Stole Christmas
    • Movies Made Here
    • Directions

Irving’s Legend

Hear the Legend told on Washington Irving's own lawn.

Washington Irving is buried a few miles up the road. Every October, his most famous story comes back to the house where he spent his last twenty years — performed outdoors, after dark, on the grounds of Sunnyside.

Master storyteller Jonathan Kruk has been doing this for decades, and he doesn't recite the tale so much as inhabit it. He plays all of them: the gangly, superstitious Ichabod Crane; the coquettish Katrina Van Tassel; swaggering Brom Bones. Jim Keyes supplies live organ music and sound effects, and a cast of shadowy figures moves at the edge of the lantern light. Then the hoofbeats start.

There's no stage, no screen, and no jump-scare gimmickry — just Irving's nineteenth-century prose, a good storyteller, and the sound of the Hudson somewhere below you in the dark. Fifty-five minutes later you'll understand why this one sells out every single year.

Know before you go

  • Where: Washington Irving's Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533
  • When: Fridays–Sundays, October 2–31, 2026. Most nights offer two or three performance times between 5 and 9 pm.
  • Run time: About 55 minutes
  • Tickets: From $40; Historic Hudson Valley members save 15%. Advance tickets only — nothing is sold at the gate, and dates sell out well before Halloween.
  • Ages: Recommended for 10 and up. It's family-friendly, but the period language, the length, and the low-light outdoor setting are a lot for younger kids.
  • Terrain: Seated outdoor performance with some walking over uneven ground. Dress for a cold night by the river.

Tickets and full schedule: hudsonvalley.org or 914-366-6900

Presented by Historic Hudson Valley.

Hear the Legend told on Washington Irving's own lawn.

Washington Irving is buried a few miles up the road. Every October, his most famous story comes back to the house where he spent his last twenty years — performed outdoors, after dark, on the grounds of Sunnyside.

Master storyteller Jonathan Kruk has been doing this for decades, and he doesn't recite the tale so much as inhabit it. He plays all of them: the gangly, superstitious Ichabod Crane; the coquettish Katrina Van Tassel; swaggering Brom Bones. Jim Keyes supplies live organ music and sound effects, and a cast of shadowy figures moves at the edge of the lantern light. Then the hoofbeats start.

There's no stage, no screen, and no jump-scare gimmickry — just Irving's nineteenth-century prose, a good storyteller, and the sound of the Hudson somewhere below you in the dark. Fifty-five minutes later you'll understand why this one sells out every single year.

Know before you go

  • Where: Washington Irving's Sunnyside, 3 W Sunnyside Lane, Irvington, NY 10533
  • When: Fridays–Sundays, October 2–31. Most nights offer two or three performance times between 5 and 9 pm.
  • Run time: About 55 minutes
  • Tickets: From $40; Historic Hudson Valley members save 15%. Advance tickets only — nothing is sold at the gate, and dates sell out well before Halloween.
  • Ages: Recommended for 10 and up. It's family-friendly, but the period language, the length, and the low-light outdoor setting are a lot for younger kids.
  • Terrain: Seated outdoor performance with some walking over uneven ground. Dress for a cold night by the river.

Tickets and full schedule: hudsonvalley.org or 914-366-6900

Presented by Historic Hudson Valley.

Primary Sidebar

Events Calendar

7 events found.
  • Week of October 4
  • Previous week
  • Next week
9:00 am
Irvington Farmers Market
October 4 @ 9:00 am - 1:30 pm

Irvington Farmers Market

Main Street School 101 Main Street, Irvington
Free
10:00 am
The Headless Horseman Files
October 4 @ 10:00 am - 4:15 pm

The Headless Horseman Files

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$25 – $35
Tarrytown Lighthouse in Sleepy Hollow Tours
October 4 @ 10:00 am - 2:00 pm

Tarrytown Lighthouse in Sleepy Hollow Tours

Free
TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
October 4 @ 10:00 am - 11:30 am

TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

418 North Broadway 418 North Broadway, Sleepy Hollow
$28
11:00 am
Ghost Tours of Tarrytown Music Hall
October 4 @ 11:00 am - 12:00 pm

Ghost Tours of Tarrytown Music Hall

Tarrytown Music Hall 13 Main Street, Tarrytown
$29
Paint a Headless Horseman with Heather Gleason
Featured October 4 @ 11:00 am - 3:00 pm

Canceled Paint a Headless Horseman with Heather Gleason

Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow
$75
Myths & Mysteries of The Octagon House
October 4 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
+ 13 More
10:00 am
Two-Day Gouache Workshop at Pocantico
October 5 @ 10:00 am - 4:30 pm

Two-Day Gouache Workshop at Pocantico

The Pocantico Center 200 Lake Road, Tarrytown
$237.62
11:00 am
Myths & Mysteries of The Octagon House
October 5 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
6:00 pm
The Great Jack O’Lantern Blaze
October 5 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
10:00 am
Two-Day Gouache Workshop at Pocantico
October 6 @ 10:00 am - 4:30 pm

Two-Day Gouache Workshop at Pocantico

The Pocantico Center 200 Lake Road, Tarrytown
$237.62
6:00 pm
The Great Jack O’Lantern Blaze
October 6 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
6:00 pm
The Great Jack O’Lantern Blaze
October 7 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
8:00 pm
Live Talks NY presents Barbara Kingsolver
October 7 @ 8:00 pm - 9:30 pm

Live Talks NY presents Barbara Kingsolver

Tarrytown Music Hall 13 Main Street, Tarrytown
$63 – $78
11:00 am
Myths & Mysteries of The Octagon House
October 8 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
6:00 pm
The Great Jack O’Lantern Blaze
October 8 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
7:00 pm
Cracking the Serial Killer Code with Dr. Katherine Ramsland
October 8 @ 7:30 pm - 9:30 pm

Cracking the Serial Killer Code with Dr. Katherine Ramsland

The Ark at the Shames JCC 371 South Broadway, Tarrytown
$38 – $43
Murder and Mayhem Walking Tour
October 8 @ 7:30 pm - 9:30 pm

Murder and Mayhem Walking Tour

Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow
$60
+ 2 More
10:00 am
The Headless Horseman Files
October 9 @ 10:00 am - 4:15 pm

The Headless Horseman Files

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$25 – $35
11:00 am
Myths & Mysteries of The Octagon House
October 9 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
2:00 pm
Spirits of Sleepy Hollow Country
October 9 @ 2:00 pm - 8:00 pm

Spirits of Sleepy Hollow Country

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$65 – $89
+ 9 More
8:00 am
TaSH Farmers Market
October 10 @ 8:30 am - 1:30 pm

TaSH Farmers Market

Patriots Park Patriots Park, Tarrytown
Free
9:00 am
Rocky’s 5k
October 10 @ 9:00 am - 11:00 am

Rocky’s 5k

Rockefeller State Park Preserve 125 Phelps Way, Pleasantville
$30 – $50
10:00 am
The Headless Horseman Files
October 10 @ 10:00 am - 4:15 pm

The Headless Horseman Files

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$25 – $35
TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
October 10 @ 10:00 am - 11:30 am

TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

418 North Broadway 418 North Broadway, Sleepy Hollow
$28
+ 22 More

Sunday, October 4, 2026

  • October 4, 2026 9:00 am - 1:30 pm
    Irvington Farmers Market
  • October 4 @ 9:00 am - 1:30 pm

    Irvington Farmers Market

    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's fresh local …

    Free
  • October 4, 2026 10:00 am - 4:15 pm
    The Headless Horseman Files
  • October 4 @ 10:00 am - 4:15 pm

    The Headless Horseman Files

    Four suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow's whodunit, staged in broad daylight. A guide walks you through the grounds of Philipsburg …

    $25 – $35
  • October 4, 2026 10:00 am - 2:00 pm
    Tarrytown Lighthouse in Sleepy Hollow Tours
  • October 4 @ 10:00 am - 2:00 pm

    Tarrytown Lighthouse in Sleepy Hollow Tours

    Step inside one of the Hudson River's most beloved landmarks. Join a 45-minute interpreter-led tour of the Tarrytown Lighthouse in Sleepy Hollow and discover the story of this 1883 cast-iron …

    Free
+ 13 More

Monday, October 5, 2026

  • October 5, 2026 10:00 am - 4:30 pm
    Two-Day Gouache Workshop at Pocantico
  • October 5 @ 10:00 am - 4:30 pm

    Two-Day Gouache Workshop at Pocantico

    Drawing inspiration from Kykuit's stunning gardens, architecture, and landscapes, participants in this two-day immersive workshop will strengthen their drawing and painting skills while exploring the expressive possibilities of gouache. Gouache …

    $237.62
  • October 5, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 5 @ 11:30 am - 4:00 pm

    Myths & Mysteries of The Octagon House

    A Halloween-season guided tour at the Armour-Stiner Octagon House, Irvington, NY For generations, the eight-sided Armour-Stiner Octagon House has inspired whispered local legends, and this fall its guides are opening …

    $38
  • October 5, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 5 @ 6:00 pm - 9:30 pm

    The Great Jack O’Lantern Blaze

    More than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …

    $24 – $189

Tuesday, October 6, 2026

  • October 6, 2026 10:00 am - 4:30 pm
    Two-Day Gouache Workshop at Pocantico
  • October 6 @ 10:00 am - 4:30 pm

    Two-Day Gouache Workshop at Pocantico

    Drawing inspiration from Kykuit's stunning gardens, architecture, and landscapes, participants in this two-day immersive workshop will strengthen their drawing and painting skills while exploring the expressive possibilities of gouache. Gouache …

    $237.62
  • October 6, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 6 @ 6:00 pm - 9:30 pm

    The Great Jack O’Lantern Blaze

    More than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …

    $24 – $189

Wednesday, October 7, 2026

  • October 7, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 7 @ 6:00 pm - 9:30 pm

    The Great Jack O’Lantern Blaze

    More than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …

    $24 – $189
  • October 7, 2026 8:00 pm - 9:30 pm
    Live Talks NY presents Barbara Kingsolver
  • October 7 @ 8:00 pm - 9:30 pm

    Live Talks NY presents Barbara Kingsolver

    Live Talks NY presents Barbara Kingsolver discussing her new novel, Partita All tickets include a copy of her novel, Partita. The story of a brief, passionate, life-changing love affair, wrapped …

    $63 – $78

Thursday, October 8, 2026

  • October 8, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 8 @ 11:30 am - 4:00 pm

    Myths & Mysteries of The Octagon House

    A Halloween-season guided tour at the Armour-Stiner Octagon House, Irvington, NY For generations, the eight-sided Armour-Stiner Octagon House has inspired whispered local legends, and this fall its guides are opening …

    $38
  • October 8, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 8 @ 6:00 pm - 9:30 pm

    The Great Jack O’Lantern Blaze

    More than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …

    $24 – $189
  • October 8, 2026 7:30 pm - 9:30 pm
    Cracking the Serial Killer Code with Dr. Katherine Ramsland
  • October 8 @ 7:30 pm - 9:30 pm

    Cracking the Serial Killer Code with Dr. Katherine Ramsland

    Calling all true crime junkies for a chilling evening with leading forensic psychologist and serial killer expert, Dr. Katherine Ramsland. For over three decades, Katherine Ramsland has studied and communicated …

    $38 – $43
+ 2 More

Friday, October 9, 2026

  • October 9, 2026 10:00 am - 4:15 pm
    The Headless Horseman Files
  • October 9 @ 10:00 am - 4:15 pm

    The Headless Horseman Files

    Four suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow's whodunit, staged in broad daylight. A guide walks you through the grounds of Philipsburg …

    $25 – $35
  • October 9, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 9 @ 11:30 am - 4:00 pm

    Myths & Mysteries of The Octagon House

    A Halloween-season guided tour at the Armour-Stiner Octagon House, Irvington, NY For generations, the eight-sided Armour-Stiner Octagon House has inspired whispered local legends, and this fall its guides are opening …

    $38
  • October 9, 2026 2:00 pm - 8:00 pm
    Spirits of Sleepy Hollow Country
  • October 9 @ 2:00 pm - 8:00 pm

    Spirits of Sleepy Hollow Country

    Sleepy Hollow has more ghosts than the Horseman. Two illusionists intend to get them talking. Mark Clearview and Nick Wallace return to Philipsburg Manor this October with an original magic show built around the spirits …

    $65 – $89
+ 9 More

Saturday, October 10, 2026

  • October 10, 2026 8:30 am - 1:30 pm
    TaSH Farmers Market
  • October 10 @ 8:30 am - 1:30 pm

    TaSH Farmers Market

    Stop by TaSH — the Tarrytown and Sleepy Hollow Farmers Market — for fresh Hudson Valley produce, meat, bread, cut flowers, dairy, preserves, wine and beer. There are weekly live music performances, children's activities, chef demos, and ongoing educational programs, plus weekly free samplings. Well-behaved dogs are welcome, provided your pooch is leashed. TaSH is …

    Free
  • October 10, 2026 9:00 am - 11:00 am
    Rocky’s 5k
  • October 10 @ 9:00 am - 11:00 am

    Rocky’s 5k

    Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first timers. If you are familiar with the Rockefeller State Park Preserve course, test your stamina and charge those uphills! First race? The Rocky’s 5K well-marked course and friendly volunteers will make it enjoyable from …

    $30 – $50
  • October 10, 2026 10:00 am - 4:15 pm
    The Headless Horseman Files
  • October 10 @ 10:00 am - 4:15 pm

    The Headless Horseman Files

    Four suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow's whodunit, staged in broad daylight. A guide walks you through the grounds of Philipsburg …

    $25 – $35
+ 22 More
View Calendar

Recent Posts

  • The Legend of Sleepy Hollow and Local Lore
  • Sleepy Hollow Music Festival
  • SUP Witches Festival
  • The Headless Horseman Files
  • Fall Crafts at Lyndhurst

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