Ossining Travel Guide

Plan your visit to Ossining with this comprehensive travel guide, including a list of places to visit, food and drink scene, where to stay, local culture, safety and health tips, and nearby destinations.


Introduction to Ossining

Located in Westchester County, in Downstate New York, in New York (state), in Mid-Atlantic, in United States of America, in North America, Ossining is a charming village with rich history, scenic beauty, and plenty of outdoor recreational activities. Formerly a farming community, Ossining is now a popular tourist destination, attracting visitors year-round for its cultural attractions, natural beauty, and proximity to New York City. Whether you’re a history buff, a nature lover, or a foodie, Ossining has something to offer for everyone.

List of Places to Visit in Ossining

Culturally Important Attractions: Museums and Historical Places

  • Sing Sing Correctional Facility Museum: Located within the historic Sing Sing Correctional Facility, this museum provides a fascinating insight into the history of the prison and its impact on American society.

  • Ossining Historical Society Museum: This museum showcases the history of Ossining through exhibits of artifacts, photographs, and documents.

  • The Old Dutch Church and Burying Ground: Built in 1685, this historic church is the oldest church in Westchester County, and the burying ground contains the graves of many Revolutionary War soldiers.

  • Eagle’s Nest Gardens: A historic mansion with stunning gardens that offer a glimpse into the Gilded Age.

Natural Attractions of Ossining: Outdoor Adventures and Scenic Views

  • Croton Gorge Park: This park offers breathtaking views of the Croton River, a waterfall, and a dam. There are also hiking and biking trails, picnic areas, and fishing spots.

  • Teatown Lake Reservation: This nature reserve is home to over 1,000 acres of forests, lakes, and meadows, with over 15 miles of hiking trails. Visitors can also participate in educational programs, bird watching, and nature walks.

  • Ossining Waterfront: A scenic waterfront location with a multitude of recreational activities, including kayaking, paddle-boarding, fishing, and hiking trails.

Hiking/Biking Routes of Ossining

  • Hudson River Walk and Bike Path: This route follows the Hudson River, offering stunning views of the water and the cliffs on the other side. The trail is approximately 18 miles long, stretching from Briarcliff Manor to Croton-on-Hudson.

  • Rockefeller State Park Preserve: A 1,400-acre park with over 55 miles of hiking trails, this park is perfect for nature enthusiasts and outdoor adventurers. The trails go through woodlands, meadows, and wetlands, with scenic views of the Hudson River.

Best Things to Do in Ossining: Activities and Tours

  • Hudson River Expeditions: A kayaking and boating tour company that offers guided tours of the Hudson River, with experienced guides who provide educational commentary about the river and its history.

  • Ossining Farmers Market: A weekly farmers market held on Saturdays, offering a wide selection of locally-grown produce, artisanal food products, and handmade crafts.

  • Ossining Food Tour: A guided walking tour of local restaurants and food shops, offering the opportunity to taste a variety of cuisines and experience the local food scene.

Week-Long Itinerary for Ossining

Day Activity
Day 1 Visit the Sing Sing Correctional Facility Museum
Day 2 Hike the Hudson River Walk and Bike Path
Day 3 Take a food tour of Ossining
Day 4 Visit the Ossining Historical Society Museum
Day 5 Kayak on the Hudson with Hudson River Expeditions
Day 6 Explore Croton Gorge Park
Day 7 Visit The Old Dutch Church and Burying Ground

Food and Drink Scene of Ossining

Must-Try Dishes

  • Ossining Pizza: Known for its delicious thin-crust pizza topped with fresh and locally sourced ingredients.

  • Hudson Valley Foie Gras: A local specialty that is considered a delicacy in the culinary world, typically served in fine dining restaurants.

  • Ossining Apple Cider Donuts: Made with freshly pressed apples, these donuts are a popular fall treat.

Local Beverages

  • Hudson Valley Wine: The region is known for its excellent vineyards and wineries, producing a variety of red and white wines.

  • Ossining Craft Beer: The growing craft beer scene in Ossining offers a variety of locally brewed beers, including IPAs, stouts, and porters.

Where to Stay in Ossining: Hotels, Hostels, and Guesthouses

  • Courtyard by Marriott: A comfortable and modern hotel located in the heart of Ossining, just minutes from the Hudson River.

  • Bricktown Inn Bed and Breakfast: A charming and cozy B&B located in a historic building that dates back to 1868.

What to Buy in Ossining: Souvenirs and Local Products to Bring Home

  • Hudson Valley Honey: Made from local bees, this honey is known for its rich flavor and health benefits.

  • Ossining Pottery: Handmade ceramics that reflect the natural beauty and history of the region, made by local artisans.

Local Culture and Customs of Ossining

Ossining has a proud history of cultural diversity, with a population that reflects a variety of ethnicities and backgrounds. The village is home to several festivals and events throughout the year, including the Ossining Village Fair, which celebrates local businesses and organizations, and the Ossining Jazz Festival, which showcases jazz musicians from around the world.

Best Time to Visit Ossining

The best time to visit Ossining is during the spring and fall, when the weather is mild, and the foliage offers stunning views. Summer is also a popular time to visit, with plenty of outdoor recreational activities and events happening throughout the season. Winter can be cold, but it can also be a beautiful time to visit, with festive holiday events and the opportunity for winter sports like skiing and snowshoeing.

Do’s and Don’ts of Ossining

Do:

  • Respect the natural beauty and wildlife of the area.

  • Try the local food and beverages.

  • Participate in cultural events and festivals.

Don’t:

  • Leave trash or litter in public spaces.

  • Ignore safety warnings and regulations.

  • Disrespect local customs and cultures.

Safety and Health

Safety in Ossining

Ossining is generally a safe and peaceful village, but visitors should still take precautions to ensure their safety, such as locking cars and keeping valuables out of sight. Hiking and outdoor activities should be approached with caution, and visitors should stay on marked trails and follow park regulations.

Health in Ossining

Ossining has several healthcare providers, including urgent care centers and hospitals. Visitors should make sure they have adequate health insurance coverage before traveling to Ossining.

Getting to Ossining: Transportation Options and Logistics

Airports Near Ossining

  • Westchester County Airport: Located approximately 12 miles from Ossining, this airport offers domestic flights and connections to major cities.

  • LaGuardia Airport: Located approximately 30 miles from Ossining, this airport offers domestic and international flights.

Bus Stations Near Ossining

  • Ossining Metro-North Station: Located in the heart of Ossining, this station offers commuter rail service to New York City and other nearby destinations.

  • Briarcliff Manor Station: Located approximately 4 miles from Ossining, this station also offers commuter rail service to New York City and other nearby destinations.

Other Options

  • Car Rental: Visitors can rent a car from several major car rental companies, including Hertz, Enterprise, and Avis.

  • Taxi and Rideshare Services: Ossining has several taxi and rideshare services for transportation within the village and to nearby destinations.

How to Get Around in Ossining

Walking is a great way to explore the village, and many of the attractions are within walking distance of each other. There are also several bike rental options available for visitors who prefer cycling. Public transportation is also available through the Metro-North railway.

Where to Go Next from Ossining: Nearby Destinations and Excursions

  • New York City: Located just 25 miles south of Ossining, New York City is a must-visit destination for cultural, entertainment, and food experiences.

  • Bear Mountain State Park: Located approximately 25 miles north of Ossining, this park offers scenic views, hiking trails, swimming and boating opportunities, and an ice rink.

  • Cold Spring: Located approximately 15 miles northeast of Ossining, this charming village offers unique shops, restaurants, and galleries, as well as hiking trails and scenic views of the Hudson River.

Conclusion

Ossining offers a unique blend of history, culture, and natural beauty that makes it an ideal travel destination for people of all ages and interests. From hiking and outdoor adventures to cultural experiences and culinary delights, Ossining is sure to leave a lasting impression on visitors. Plan your visit to Ossining today and discover all the village has to offer.