Things To Do
in Sleepy Hollow

Sleepy Hollow, New York, is a quaint village located along the Hudson River, known for its rich history and ties to Washington Irving's 'The Legend of Sleepy Hollow.' Nestled in Westchester County, it features lush landscapes, historic sites, and a charming downtown area. The village is particularly famous for its Halloween celebrations and the annual Great Jack O'Lantern Blaze.

Visitors can explore landmarks, enjoy outdoor activities, and immerse themselves in local folklore.

Day Trips

Spend a day exploring around

day 1
Day 1: Historic Exploration
morning
:

Start your day with a visit to the Sleepy Hollow Cemetery, where you can see the graves of Washington Irving and other notable figures.

afternoon
:

Head to the Old Dutch Church, a historic site that dates back to the 17th century, followed by a stroll through the nearby trails.

evening
:

Enjoy dinner at a local restaurant and then take a ghost tour to learn more about the village's folklore.

day 2
Day 2: Nature and Relaxation
morning
:

Begin your morning at the Rockefeller State Park Preserve, exploring its scenic trails and picturesque landscapes.

afternoon
:

Visit the Philipsburg Manor, a historic site that offers guided tours and interactive exhibits.

evening
:

Wrap up your day with a relaxing evening by the Hudson River, taking in the sunset views and enjoying a casual meal at a riverside café.

Cost Guide

Prices

ItemPrice
🍔Meal at a restaurant$20-$40
Coffee$3-$5
🏨Hotel room (per night)$150-$300
🚗Car rental (per day)$50-$100
🚌Public transport fare$2-$5

Strengths and Weaknesses

  • Rich historical background and folklore
  • Beautiful natural scenery and outdoor activities
  • Charming small-town atmosphere
  • Limited nightlife options
  • Can be crowded during Halloween season
  • Public transport options are limited

Places to Visit in Sleepy Hollow

Visit one of these nice places.

Sleepy Hollow Cemetery

This historic cemetery offers a hauntingly beautiful setting with its ancient trees and notable graves.

The Old Dutch Church

A picturesque church dating back to 1685, surrounded by stunning landscapes and historic architecture.

Hudson River Waterfront

The waterfront provides breathtaking views of the river, especially at sunset, making it ideal for photography.

Culinary Guide

Food in Sleepy Hollow

Sleepy Hollow offers a delightful culinary scene that reflects its rich history and local flavors. Visitors can enjoy a variety of dining options ranging from casual eateries to fine dining establishments.

Sleepy Hollow Famous Food

Signature dishes, delicacies and famous food

Hudson Valley Apple Pie

A local favorite made with fresh apples from nearby orchards, often served with a scoop of vanilla ice cream.

Must-Try!

Pumpkin Ale

Seasonal craft beers brewed with local pumpkins, perfect for the fall season.

Food Markets

Explore local food markets

Sleepy Hollow Farmers Market

Held weekly, this market features fresh produce, artisanal products, and local delicacies from various vendors.

Climate Guide

Weather

Sleepy Hollow experiences a humid continental climate, with four distinct seasons. Summers are warm and humid, averaging temperatures in the mid-80s°F (29°C). Winters are cold, with average lows around 24°F (-4°C), often accompanied by snow. Spring and fall are mild and pleasant, making them ideal for outdoor activities.

How to Behave

Tips on cultural norms and respectful behavior

Respect for History

Visitors should show respect for the historical sites and adhere to any posted guidelines.

Quiet at Night

As a small village, keeping noise levels down in residential areas during the night is appreciated.

Friendly Greetings

Locals appreciate friendly greetings; a simple 'hello' can go a long way.

Safety Guide

Safety

Sleepy Hollow is generally a safe place to visit, but like any destination, it's important to remain aware of your surroundings. Use common sense, avoid poorly lit areas at night, and secure your belongings. Emergency services can be reached via 911, and local police are present to assist visitors.

Tipping in Sleepy Hollow

Ensure a smooth experience

Tipping Customs

It is customary to tip around 15-20% in restaurants, and rounding up for service is appreciated.

Payment Methods

Credit cards are widely accepted, but it is advisable to carry some cash for small vendors or markets.

Best Time to Visit

And what to expect in different seasons...

Spring

Spring brings blooming flowers and mild temperatures, perfect for outdoor activities and festivals.

Summer

Summer is warm and sunny, ideal for enjoying the riverfront and outdoor dining, but can also be humid.

Fall

Fall is vibrant with colorful foliage, especially beautiful in October, making it a popular time for visitors.

Winter

Winter can be cold and snowy, offering a serene landscape, but be prepared for chilly temperatures.

Nightlife Guide

Sleepy Hollow at Night

Sleepy Hollow has a relaxed nightlife scene, predominantly composed of cozy pubs and casual dining establishments. While the village is not known for a vibrant club scene, it offers a few bars where locals gather to unwind, enjoy live music, and socialize. Seasonal events often bring a festive atmosphere, especially during Halloween when themed activities and parties take place.

Hiking in Sleepy Hollow

Immerse in an unforgettable hike.

Tallman Mountain State Park

This park features several trails with varying difficulty levels, offering scenic views of the Hudson River.

Croton Point Park

A beautiful park with trails along the river, suitable for hiking, picnicking, and birdwatching.

Airports

How to reach Sleepy Hollow by plane.

Westchester County Airport (HPN)

Located about 12 miles from Sleepy Hollow, this airport offers domestic flights and is the most convenient option for visitors.

Getting Around

Walkability

Sleepy Hollow is relatively walkable, especially in the downtown area where shops, restaurants, and attractions are concentrated. Sidewalks are present, but some areas may require walking along the road. The village's small size makes it easy to explore on foot, particularly during pleasant weather.

Demographics

Explore demographics in this area.

Families

Many families reside in Sleepy Hollow, attracted by the village's schools, parks, and sense of community.

Young Professionals

A growing number of young professionals live in the area, commuting to nearby cities for work while enjoying the village's charm.

Popular Sports

Explore popular sports in region.

Baseball

Baseball is a popular pastime in the area, with local leagues and teams engaging community members.

Soccer

Soccer has gained popularity, with youth leagues and community events held regularly.

Transportation

Traffic

Traffic in Sleepy Hollow can vary, especially during peak tourist seasons and weekends. The village is accessible via major roads, and parking can be limited in busy areas. Public transportation options include the Metro-North Railroad, which provides convenient access to New York City and surrounding regions.

Accomodations

Find the best place to stay when visiting Sleepy Hollow.

Dietary Restrictions

Tips for restricted diets.

Vegetarian Options

Many restaurants offer vegetarian-friendly dishes, but it's advisable to check the menu or ask staff.

Gluten-Free Choices

Several eateries provide gluten-free options; be sure to inform your server of specific dietary needs.

Health & Medical

Healthcare

Healthcare access in Sleepy Hollow is primarily provided through nearby hospitals and clinics in Tarrytown and the surrounding areas. The closest major hospital is NewYork-Presbyterian Hospital, which offers comprehensive medical services. Urgent care facilities are also available for non-emergency situations.

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