Ossining, New York, USA (Sing Sing)
Whether you're a local looking for new experiences or a visitor exploring the area, here's a list of places to go and things to do in and around Ossining:

Visit Sing Sing Prison Museum: Start your journey by exploring the history of the infamous Sing Sing Correctional Facility. This museum provides an in-depth look into the prison's history, including its past inmates and the role it has played in criminal justice.

Hike at Teatown Lake Reservation: If you're a nature enthusiast, you'll love the Teatown Lake Reservation. There are numerous trails to explore, offering beautiful views of Teatown Lake and the surrounding woods. It's a great spot for bird-watching and getting in touch with the local flora and fauna.

Ossining Farmers' Market: On Saturdays, be sure to check out the Ossining Farmers' Market. It's a fantastic place to buy fresh, locally sourced produce, artisanal goods, and delicious prepared foods. You can also interact with local farmers and vendors, making it a true community experience.

Ossining Historical Society Museum: Dive into Ossining's past at the Ossining Historical Society Museum. Learn about the village's history, including its role in the Revolutionary War and the development of the area over the centuries.

Croton Aqueduct Trail: Take a stroll or bike ride along the Old Croton Aqueduct Trail, a historic water supply system that once provided New York City with fresh water. It's a scenic path that winds through the woods and passes by picturesque stone bridges.

Rockefeller State Park Preserve: Just a short drive from Ossining, this park offers over 1,000 acres of walking, jogging, and horseback riding trails. You can explore woodlands, meadows, and serene lakes while enjoying the fresh air.

Visit the Old Dutch Church: Built in 1685, the Old Dutch Church of Sleepy Hollow is a historic gem located nearby. This charming church and its cemetery are steeped in history and have connections to Washington Irving's "The Legend of Sleepy Hollow."

Kykuit, the Rockefeller Estate: Take a guided tour of the grand Kykuit estate, once home to four generations of the Rockefeller family. The estate features impressive architecture, beautiful gardens, and stunning views of the Hudson River.

Hudson Valley Center for Contemporary Art: Art enthusiasts will appreciate this contemporary art center, which hosts rotating exhibitions of contemporary art, installations, and sculptures. It's a great place to discover emerging artists and thought-provoking pieces.

Explore the Hudson River: The Hudson River plays a significant role in Ossining's history and culture. You can enjoy the river by going on a boat tour or simply taking a leisurely walk along the waterfront. Don't forget to snap some photos of the stunning sunsets over the river.

Ossining Public Library: If you're looking for a quiet place to read, study, or catch up on work, the Ossining Public Library is a welcoming spot. They often host events, lectures, and workshops, so check their schedule for interesting programs.

Shop and Dine in Downtown Ossining: Stroll through downtown Ossining to discover charming shops, boutiques, and a variety of restaurants. Whether you're in the mood for a cozy café, ethnic cuisine, or classic American fare, you'll find plenty of dining options.

Ossining Arts Project: Keep an eye out for public art installations and murals throughout Ossining. The Ossining Arts Project brings art to the streets, making it an open-air gallery for everyone to enjoy.

Ossining Waterfront Park: This park offers a scenic spot along the Hudson River with picnic areas, playgrounds, and walking paths. It's a great place for a family outing or a relaxing afternoon by the water.

Attend Local Events: Ossining hosts various events and festivals throughout the year, including music concerts, art shows, and community gatherings. Check the village's event calendar to see what's happening during your visit.

Visit Nearby Historic Sites: Ossining is conveniently located near several historic sites, including Philipsburg Manor, Sunnyside (Washington Irving's home), and Lyndhurst Mansion. Explore these fascinating properties to gain insight into the region's history.

Tee Off at the Sleepy Hollow Country Club: If you're a golfer, book a round at the prestigious Sleepy Hollow Country Club, known for its beautiful course and scenic views.

Kayaking on the Hudson River: During the warmer months, consider renting a kayak and exploring the Hudson River from a different perspective. It's a fun and active way to enjoy the outdoors.

Ossining Arts Council Gallery: This gallery showcases the works of local artists, providing a platform for creativity and cultural expression. Check their schedule for exhibitions and art-related events.

Ossining Boat and Canoe Club: If you're interested in boating or canoeing, consider joining the Ossining Boat and Canoe Club. They offer a variety of activities and events for members.



Visit Ossining, New York, USA (Sing Sing)
Discover the people who lived there, the places they visited and the stories they shared.