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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
Fresh apples from Mead Orchard at Tarrytown and Sleepy Hollow Farmers Market.

Apple Picking

There's nothing better in the Fall than apple picking and hot cider donuts! Some of our favorite orchards are just a short drive from downtown Sleepy Hollow. Start planning your weekend of fresh cider, Fall festivals, and pumpkin and apple picking!

Here's a tip for making a full day of it: most of these orchards are a 25–35 minute drive from the village, and most are at their best in the morning before the weekend crowds build. That makes picking a natural first stop — head out early, fill your bags and grab cider donuts, then come back to spend the afternoon and evening in Sleepy Hollow itself. A morning at the orchard pairs perfectly with an afternoon cemetery tour and a fall evening in the village; see A Perfect Fall Day in Sleepy Hollow for how to put it all together. One thing to note: nearly all of these are well outside the village, so this is the one fall outing you'll really want a car for — it's not a stop on the car-free itinerary.


Wilkins Fruit & Fir Farm offers apple picking and more.Wilkens Fruit & Fir Farm

Wilkens is the closest place to pick your own, just 14 miles from Sleepy Hollow. They sell a wide variety of apples, pumpkins and peaches. Don't miss their own bakery and apple cider pressed on site. There is a seasonal corn maze to wander and a winery producing from the farm's own grapes. There is also a country market, showcasing local crafts. Allow around 30 minutes travel time.

Location: 1335 White Hill Road, Yorktown Heights, NY 10598


Stuart's Fruit Farm

Family operated since 1828, Stuart's offers pick-your-own apples and pumpkins. Check the farm stand for seasonal fruit and vegetables. At the bakery there are cider donuts, pies and other treats. Enjoy a hayride around the farm on Fall weekends! About 20 miles from Sleepy Hollow, allow around 30 minutes travel time.

Location: 62 Granite Springs Road, Granite Springs NY, 10527


Dr. Davies Farm

This Rockland County farm has been in the Davies family since the late 1800s. There is apple picking in season, varieties including Macintosh. Empire, Winesap, Fuji and more. The farm stand offers local produce. Cash only, here. About 15 miles from Sleepy Hollow, allow around 25 minutes travel time. The seasonal Red Barn Cidery on location serves local hard cider, beer and wine.

Location: 306 NY-304, Congers, NY 10920


Salinger's Orchards

Established in 1901, the 4th generation of Salingers is still working the land. Salinger's grows eighteen varieties of apples as well as peaches, pears, nectarines, plums, cherries, and other seasonal crops. The bakery on site operates year round, serving up delicious fresh pies, cider donuts, pastries and more. The farm store stocks raw local honey, maple syrup, preserves, fresh produce, and more. About 25 miles from Sleepy Hollow, allow around 30 minutes travel time.

Location: 230 Guinea Road Brewster, NY 10509


Harvest Moon offers apple picking, fresh and hard cider, and Fall festivals.Harvest Moon Farm and Orchard

Harvest Moon Farm & Orchard is a family owned and operated apple orchard.

The farm store offers a bounty of seasonal products including pasture-raised meats, dairy, and fresh produce, much of it grown right here on the farm or nearby in the Hudson Valley. The bakery turns out fresh apple cider donuts, pies, bread and other baked treats. Hardscrabble Cider presses both sweet and hard cider.

Harvest Moon goes all out in the Fall. There's apple and pumpkin picking, fresh produce, fresh churned ice cream, kids actives. Even an apple cannon!

About 25 miles from Sleepy Hollow, allow around 30 minutes travel time.

Location: 130 Hardscrabble Road, North Salem, NY 10560


Outhouse Orchards

Pick your own apples, pears and pumpkins in season. In the Fall, there are hayrides and a corn maze. The bakery on site turns out cider donuts, pies and more!

The Outhouse family has been farming here since the 1800s. The retail side of the orchard was started by the colorfully named A. Purdy Outhouse. Despite the connotation, the family name was originally Dutch: Althouse.

About 25 miles from Sleepy Hollow, allow around 30 minutes travel time.

Location: 139 Hardscrabble Road, North Salem, NY 10560


The Orchards of Concklin

Concklins have been farming the land in this area since 1711. Pick your own apples and enjoy fresh baked pies and other treats.

About 16 miles from Sleepy Hollow, allow around 30 minutes travel time.

Location: 2 South Mountain Road, Pomona, NY 10970

Primary Sidebar

Events Calendar

7 events found.
  • Week of October 11
  • Previous week
  • Next week
9:00 am
Irvington Farmers Market
October 11 @ 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 11 @ 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 11 @ 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 11 @ 11:00 am - 12:00 pm

Ghost Tours of Tarrytown Music Hall

Tarrytown Music Hall 13 Main Street, Tarrytown
$29
Myths & Mysteries of The Octagon House
October 11 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
+ 17 More
11:00 am
Myths & Mysteries of The Octagon House
October 12 @ 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 12 @ 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 13 @ 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 14 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
11:00 am
Myths & Mysteries of The Octagon House
October 15 @ 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 15 @ 6:00 pm - 9:30 pm

The Great Jack O’Lantern Blaze

Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson
$24 – $189
Masque of the Red Death at Lyndhurst
October 15 @ 6:00 pm - 9:00 pm

Masque of the Red Death at Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$45
7:00 pm
Peek-a-Boo (An Immersive Hudson Valley Haunt)
October 15 @ 7:30 pm - 9:00 pm

Peek-a-Boo (An Immersive Hudson Valley Haunt)

Bethany Arts Community 40 Somerstown Road, Ossining
$27 – $47
Murder and Mayhem Walking Tour
October 15 @ 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 16 @ 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 16 @ 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 16 @ 2:00 pm - 8:00 pm

Spirits of Sleepy Hollow Country

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$65 – $89
+ 15 More
8:00 am
TaSH Farmers Market
October 17 @ 8:30 am - 1:30 pm

TaSH Farmers Market

Patriots Park Patriots Park, Tarrytown
Free
10:00 am
TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
October 17 @ 10:00 am - 11:30 am

TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

418 North Broadway 418 North Broadway, Sleepy Hollow
$28
The Goblin Market
October 17 @ 10:00 am - 3:00 pm

The Goblin Market

Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow
Free
The Headless Horseman Files
October 17 @ 10:00 am - 4:15 pm

The Headless Horseman Files

Philipsburg Manor 381 North Broadway, Sleepy Hollow
$25 – $35
Christ Church/San Marcos Annual Fall Fair
October 17 @ 10:00 am - 4:00 pm

Christ Church/San Marcos Annual Fall Fair

Christ Church San Marcos 43 South Broadway, Tarrytown
Free
Warner Library Fall Book Sale
October 17 @ 10:00 am - 5:00 pm

Warner Library Fall Book Sale

Warner Library 121 North Broadway, Tarrytown
Free
11:00 am
Trick-or-Treat Weekend at Lyndhurst
October 17 @ 11:00 am - 4:00 pm

Trick-or-Treat Weekend at Lyndhurst

Lyndhurst 635 South Broadway, Tarrytown
$5 – $30
Ghost Tours of Tarrytown Music Hall
October 17 @ 11:00 am - 12:00 pm

Ghost Tours of Tarrytown Music Hall

Tarrytown Music Hall 13 Main Street, Tarrytown
$29
Myths & Mysteries of The Octagon House
October 17 @ 11:30 am - 4:00 pm

Myths & Mysteries of The Octagon House

Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington
$38
+ 20 More

Sunday, October 11, 2026

  • October 11, 2026 9:00 am - 1:30 pm
    Irvington Farmers Market
  • October 11 @ 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 11, 2026 10:00 am - 4:15 pm
    The Headless Horseman Files
  • October 11 @ 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 11, 2026 10:00 am - 11:30 am
    TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
  • October 11 @ 10:00 am - 11:30 am

    TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

    Embark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, …

    $28
+ 17 More

Monday, October 12, 2026

  • October 12, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 12 @ 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 12, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 12 @ 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 13, 2026

  • October 13, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 13 @ 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 14, 2026

  • October 14, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 14 @ 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

Thursday, October 15, 2026

  • October 15, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 15 @ 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 15, 2026 6:00 pm - 9:30 pm
    The Great Jack O’Lantern Blaze
  • October 15 @ 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 15, 2026 6:00 pm - 9:00 pm
    Masque of the Red Death at Lyndhurst
  • October 15 @ 6:00 pm - 9:00 pm

    Masque of the Red Death at Lyndhurst

    This October, Lyndhurst Mansion transforms into Prince Prospero’s abbey for an immersive theater experience drawn from Edgar Allan Poe’s The Masque of the Red Death. As a guest of Prospero, …

    $45
+ 2 More

Friday, October 16, 2026

  • October 16, 2026 10:00 am - 4:15 pm
    The Headless Horseman Files
  • October 16 @ 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 16, 2026 11:30 am - 4:00 pm
    Myths & Mysteries of The Octagon House
  • October 16 @ 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 16, 2026 2:00 pm - 8:00 pm
    Spirits of Sleepy Hollow Country
  • October 16 @ 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
+ 15 More

Saturday, October 17, 2026

  • October 17, 2026 8:30 am - 1:30 pm
    TaSH Farmers Market
  • October 17 @ 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 …

    Free
  • October 17, 2026 10:00 am - 11:30 am
    TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
  • October 17 @ 10:00 am - 11:30 am

    TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

    Embark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, …

    $28
  • October 17, 2026 10:00 am - 3:00 pm
    The Goblin Market
  • October 17 @ 10:00 am - 3:00 pm

    The Goblin Market

    Hudson Valley Writers Center opens its historic building for an October pop up with local artists and creators! Drop in for artwork, crafts, and other goods from Sleepy Hollow creators. …

    Free
+ 20 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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