Explore Sleepy Hollow, NY

Less than 30 miles from Midtown Manhattan lies the quaint village of Sleepy Hollow in Westchester County, New York. Each fall, this picturesque destination, which has a population of just under 11,000, attracts throngs of thrill-seeking travelers.

Where to Stay in Sleepy Hollow

Sleepy Hollow Hotel

The Sleepy Hollow Hotel is one of the village’s very few hotels. The property spans 11 acres of grassy, tree-lined grounds. When guests aren’t exploring, they can relax in the lap pool, unwind in the sauna, or enjoy breakfast staples at Bistro Z Restaurant.

Tarrytown House Estate on the Hudson

A few minutes down the road in nearby Tarrytown, travelers can choose from historic hotels with castle-like exteriors. Tarrytown House Estate on The Hudson is ideal for families, featuring an indoor pool, seasonal outdoor pool, and on-site sports, including tennis and racquetball. The estate’s 26-acre grounds and the stylish Goosefeather restaurant serving modern Cantonese fare are added bonuses.

The Castle Hotel & Spa

The Castle Hotel & Spa is perfect for a romantic escape. Surrounded by 10 acres of tranquil woodland, this renovated castle features 31 rooms with en-suite fireplaces and marble baths. Guests can also enjoy an upscale American eatery, spa treatments, and manicured gardens.

Things to Do in Sleepy Hollow

Kykuit, the Rockefeller Estate

This former residence of the Rockefeller family—comprising a 40-room mansion and gardens—is now a historic landmark, open seasonally from May to November. Its gardens and art collections are captivating, making it a must-visit regardless of the season.

Philipsburg Manor

Visitors can explore Philipsburg Manor, a former mill complex, to learn about the enslaved individuals who lived here in the 18th century. Keep in mind that the site is only open on select dates between May and December.

Old Dutch Church

The Old Dutch Church dates back to 1685 and is famous for its appearance in “The Legend of Sleepy Hollow.” Its 2.5-acre burying ground serves as the supposed home of the Headless Horseman.

Sleepy Hollow Cemetery

The historic Sleepy Hollow Cemetery is the final resting place for over 45,000 individuals, including Washington Irving. The cemetery is open daily, offering various walking tours. Nearby, visitors can find the iconic Headless Horseman Bridge and Statue.

Where to Eat and Drink in Sleepy Hollow

Hudson Farmer & The Fish

Located on the Sleepy Hollow Riverwalk, Hudson Farmer & The Fish offers seasonal specialties, a raw bar, and modern takes on seafood classics. Autumnal-inspired dishes like pumpkin bisque add to the dining experience, complemented by beautiful Hudson River views.

J.P. Doyle’s

J.P. Doyle’s is a charming Irish pub celebrated for its warm atmosphere. Known for one of the best burgers in town (the Horseman Burger), this spot is popular with both locals and visitors.

Bridge View Tavern

Beer enthusiasts will love Bridge View Tavern for its craft beer selection, perfectly paired with dishes like pulled pork sandwiches, disco fries, and smoked chicken wings.

Hudson Anchor Restaurant

Offering a variety of dishes from pasta to steak, Hudson Anchor Restaurant features a happy hour with discounts on cocktails, beer, and food. If the weather’s nice, enjoy a meal on the rooftop deck.

Santorini Greek Restaurant

If you’re craving Greek cuisine, Santorini Greek Restaurant is a great choice, offering delicious dips and gyros.

Halloween in Sleepy Hollow

Sleepy Hollow truly comes alive during the Halloween season. With numerous Halloween-centric events, the village attracts hundreds, if not thousands, of tourists. Here are some highlights.

The Legend Cirque

This immersive performance, adapted from “The Legend of Sleepy Hollow,” features live-action circus performances and runs through Oct. 29, suitable for ages eight and up.

The Horsemen: Terror Lies in Chaos

Thrill-seekers shouldn’t miss the spectacular haunted house experience, running from Oct. 6 to Nov. 5. It’s recommended for those 16 and older, with strict age restrictions in place.

Sleepy Hollow Cemetery Events

During the spooky season, Sleepy Hollow Cemetery hosts special events, including murder mystery parties and storytelling evenings with Washington Irving. These tours provide a unique insight into the lives of its famous residents, especially under moonlit skies.

SUP Witches Festival

On Oct. 15, the SUP Witches Festival features witches paddling at Horan’s Landing. Costume participation and advance registration are required.

Haunted Hayride and Block Party

On Oct. 20 or 21, experience the Haunted Hayride, which carries passengers through downtown. After the ride, enjoy a free block party featuring live music and family-friendly activities.

Run for Your Life 10K

On Oct. 28, join the annual “Run for Your Life” Halloween 10K, where participants are encouraged to dress in costumes for a fun Halloween twist.

Irving’s Legend at Sunnyside

On select dates, visit Irving’s home in Tarrytown, festively decorated for the season. While the event is only open through Halloween, the estate remains accessible until Dec. 17.

Lyndhurst Mansion

Lyndhurst, a historic mansion in Tarrytown, is also worth visiting. The ‘Classic Fall Mansion Tour’ allows guests to admire the house adorned with autumn splendor.

Best Time to Visit

The best time to visit Sleepy Hollow depends on your interests. For spooky enthusiasts, fall, particularly October, is ideal due to Halloween events and peak foliage. However, Sleepy Hollow is a great weekend getaway year-round, especially given its proximity to New York City.

How to Get There

Travelers arriving by car will find Sleepy Hollow conveniently located near major thoroughfares like I-287. For a stress-free journey, consider public transportation via Metro-North trains to Philipse Manor Station in Sleepy Hollow or Tarrytown Station, both a short distance from local attractions.

Additionally, Westchester County Airport is just 20 miles away, while NYC airports like LaGuardia, JFK, and Newark are within a 45-mile radius.