With a famous name that appeals to the Halloween fan in everyone, Sleepy Hollow is a great weekend getaway destination, and not only on October 31. As the birthplace of the Headless Horseman, and with neighboring Tarrytown being the former home of Legend of Sleepy Hollow author Washington Irving, the village goes all out for Halloween, with weekly festivals, hayrides, and parades. The area also offers a plethora of multi-season attractions that travelers can enjoy all year round. Photo Credit: @arturoexplores on Instagram.

This article was originally published on 10/31/2017 and last updated on 09/17/2026.

EXPLORE THIS ARTICLE:

  1. Things To Do On a Fall Weekend in Sleepy Hollow
  2. Where To Eat On a Fall Weekend in Sleepy Hollow
  3. Where To Stay On a Fall Weekend in Sleepy Hollow

Things To Do On a Fall Weekend in Sleepy Hollow

Lyndhurst mansion during the golden hour Credit: @jahv on Instagram

1. Take a tour of the Gothic Revival Mansion, Lyndhurst

Start your weekend with a morning guided tour of historic Lyndhurst (pictured), whose exterior was used for movies based on the classic vampire soap opera Dark Shadows. See the Gothic Revival mansion all decked out for the autumn season on a Fall Classic Mansion Tour and enjoy a series of Halloween Season events including Trick-or-Treat Weekend, Gothic Market, a Dark Shadows walking tour, and meet-and-greet with Dark Shadows star Kathryn Leigh Scott.

2. Visit Washington Irving’s Sunnyside Estate

Washington Irving’s Sunnyside estate

An afternoon visit to Washington Irving’s Sunnyside estate (pictured) allows you to take a tour of the author’s riverside home and admire its unique architecture along with the expansive Hudson River views. You’ll hear about what led Irving to write his most famous short story, see an original shadow puppet short film, and enjoy lawn games on the Legendary Tours, happening through November 8, 2026. 

3. Take a Tour of Sleepy Hollow Cemetery

Rich orange leaves blanket Sleepy Hollow Cemetery in the fall
Credit: @arturoexplores on Instagram

The final resting place of Washington Irving, William Rockefeller, Walter Chrysler, Andrew Carnegie, and Samuel Gompers, you can take a guided walking tour of the 90-acre Sleepy Hollow Cemetery (pictured) by day or night (with the help of the glow from kerosene lantern light). The stories of Dracula, Frankenstein and more to come to life during special fall-time performances at the Washington Irving Memorial Chapel.

4. Step into The Legend of Sleepy Hollow at Old Dutch Church

Legend of Washington Irving Performer at Old Dutch Church of Sleepy Hollow

Old Dutch Church of Sleepy Hollow is the stone church and adjoining burial ground featured in Irving's tale, the haunt of the headless horseman. Self-guided visits to the grounds are available until 4:30 pm. For six nights only in October 2026, encounter Ichabod Crane and the Headless Horseman during a riveting reading of The Legend of Sleepy Hollow on the Old Dutch Church grounds (tickets required).

5. Catch One-Of-A-Kind Events at Philipsburg Manor

Smiling woman in a rustic wolf costume, with a wolf puppet perched on her head, playfully raises clawed hands outside Philipsburg Manor during their Halloween festivities.

In October, the 18th-century Philipsburg Manor, which also made an appearance in Irving's chilling tale, transforms into Twilight Village filled with live storytellers, fire performers, a pop-up market with curious goods, roving brass band, and more on weekend evenings. During the day, watch a Sleepy Hollow whodunit unfold during The Headless Horseman Files 45-minute walk through the historic grounds.

6. Snap a Photo with the Headless Horseman Statue

An 18-foot steel sculpture depicting the Headless Horseman chasing Ichabod Crane stands in Sleepy Hollow Credit: @legendsofsleepyhollow on Instagram

Looking for the perfect photo op to remember your trip? Check out this 18-foot-tall sculpture depicting the Headless Horseman chasing Ichabod Crane, located between Philipsburg Manor and the Old Dutch Church.

7. Spend Time in Nature at Rockefeller State Park Preserve

A weathered stone bridge arches over a stream in a quiet autumn forest, surrounded by vivid red, orange, and golden fallen leaves at Rockefeller State Park Preserve.

Rockefeller State Park Preserve offers seasonal activities including hiking, running, bird-watching, fishing (New York state fishing license required), picnicking, photography, and painting. Special events, including bird photography workshops and full moon hikes, are also available. Download the New York State Parks Explorer app to plan your visit. 

8. Bask in the Glow of the Great Jack O'Lantern Blaze

A woman in a striped sweater and cowboy hat walks under a jack o'lantern archway at Blaze: Long Island Credit: @sahquart on Instagram

Just a 20-minute drive from Sleepy Hollow, marvel at the Great Jack O'Lantern Blaze as it lights up Van Cortlandt Manor with 7,000 uniquely hand-carved and illuminated pumpkins. Spot iconic New York landmarks, stroll the Pumpkin Promenade, hang out at the Headless Horseman’s Hideaway or relax in the Gourd & Goblet Tavern, and more as you enjoy one of the Hudson Valley's best events of the season.

Where To Eat On a Fall Weekend in Sleepy Hollow

Close-up of a hand holding a foamy latte topped with playful jack-o’-lantern art, evoking a cozy, festive autumn mood at Coffee Labs Roasters in Tarrytown. Credit: @sleepyhollowspellbound on Instagram

Sleepy Hollow and neighboring Tarrytown have a deep immigrant history resulting in a rich mix of cuisines: Italian, Greek, Mexican, Indian, French, Portuguese, Irish, Japanese, Dominican, Chinese, Ecuadorian, Thai, Moroccan, and Chilean. Don't miss the Tarrytown and Sleepy Hollow Farmers Market at Patriots Park on Saturdays from 8:30 am-1:30 pm, where you’ll find fresh Hudson Valley produce, meat, bread, and wine.

  • No fall outing is complete without a pumpkin spice latte. Stop by Coffee Labs Roasters in Tarrytown for their take on the seasonal favorite, The Great Pumpkin (pictured).

  • Lefteris Gyro along Tarrytown’s charming Main Street offers the perfect lunch option—it’s casual and easy, suitable for the whole family.

  • Sweet Grass Grill is a gorgeous farm-to-table restaurant in Tarrytown that offers something for everyone.

  • Eatarry serves up hearty breakfast, lunch, brunch, and afternoon tea from their cozy interior in Tarrytown.

  • Bridge View Tavern in Sleepy Hollow is perfect for beer lovers with at least 15 beers on tap and an emphasis on craft and regional brews. Order any of their award-winning beers or try a limited-release specialty and pair it with delicious food from their seasonally fresh menu.

  • Local brewery Captain Lawrence in nearby Elmsford has an expansive outdoor beer garden and 2,500 square foot beer hall.

Where To Stay On a Fall Weekend in Sleepy Hollow

Inside hotel lobby

Set the scene for your Sleepy Hollow getaway with a reservation at The Sleepy Hollow Hotel in Tarrytown. Situated in a beautiful country atmosphere with stone fireplaces scattered throughout, settle into one of 246 welcoming guest rooms, and enjoy the on-site award-winning restaurant, Hudson Bistro. 

FairBridge Inn Express in Nyack is a great budget option. Located just over the river, it's about six miles from Tarrytown, seven miles from Sleepy Hollow.

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