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The Best of Ossining: Top 3 Reasons to Live and Play Here

Picture this! You’re strolling by the riverside, the sun sinking beneath the horizon, casting a vibrant tapestry of pink and orange hues. Aromas of freshly caught seafood fill the air, while the joyful sounds of loved ones resonate throughout.
It’s a Friday evening in Ossining, and you can’t help but feel alive. Welcome to your new favorite hometown.
If you’re planning a move to Ossining and can’t wait to uncover its unique appeal, you’re in luck. I’m here to tell you about the top three reasons why Ossining, New York, is the ideal spot to live, play, and (spoiler alert!) fall in love with. Let’s start!

Top 3 Reasons to Live and Play in Here

Ossining Greenway Trail

A Scenic Retreat with Easy Access to Manhattan

Ossining’s location is among the most convincing arguments for living here. Being only 30 miles north of Manhattan, Ossining provides a tranquil escape from city life’s hustle and bustle. The village provides a serene environment with stunning waterfront views, lush parks, and a tight-knit community. Despite its tranquility, Ossining enjoys easy access to New York City via the Metro-North Railroad, making it an ideal home base for commuters or anyone that likes to enjoy spening time in the city.

Rich History and Architectural Beauty

Ossining boasts a fascinating history dating back to the 18th century. Many of the village’s historic buildings have been preserved, including the Old Croton Aqueduct and the impressive Victorian homes that line the streets. Ossining is also home to Sing Sing Prison, which has played a significant role in shaping the area’s history. The town’s affluent history and architectural elegance add to its exceptional personality, making it an attractive location to reside in or explore. 

A Vibrant Community with Plenty to Do

Ossining residents enjoy a plethora of activities and amenities. The village’s picturesque parks, bustling downtown, and diverse dining options offer something for everyone. In addition, Ossining boasts an active arts and cultural scene, with art galleries, theaters, and a thriving local music scene.

Things To Do In Ossining

  1. Teatown Lake Reservation: Discover 1,000 Acres of Natural Beauty – The Teatown Lake Reserve in Ossining is a must-see location if you enjoy being in nature. This nature reserve spans 1,000 acres and provides hiking trails, wildlife exhibits, and environmental education programs, allowing visitors to explore and appreciate the natural splendor of the Hudson Valley. With more than 15 miles of paths, you may go hiking, observe birds, or simply enjoy the environment.

  2. Louis Engel Waterfront Park: Relax by the Hudson River – The Louis Engel Waterfront Park, located along the Hudson River, is the ideal location to unwind, take in a picnic, or attend an outdoor music in the summer. Because of its vast river panoramas and numerous shaded areas, both locals and visitors appreciate this park. This spot is also excellent for a family adventure.
  3. The Old Croton Aqueduct Trail: Hike or Bike along Historic Trail – Those who enjoy the outdoors and history will enjoy touring the Historic Croton Aqueduct Trail. You can jog, stroll, or bike along this historical route, originating from the mid-1800s, while appreciating the Hudson River’s remarkable panoramas and surrounding rural landscapes. It’s a wonderful opportunity to enjoy the region’s natural beauty and history simultaneously.
  4. Ossining Public Library: Discover a Wealth of Resources – The Ossining Public Library is a favorite destination for book enthusiasts and anyone seeking a quiet spot to relax in Ossining. Numerous resources are accessible at this innovative venue, including books, magazines, movies, and more. Also, the library offers a range of programming for people of all ages, such as tech classes, reading groups, and storytimes.
  5. Sing Sing Prison Museum: Learn about the History of Infamous Prison – A wonderful place to learn about the past of this notorious jail, which was in use for more than 150 years, is the Sing Sing Prison Museum. Visitors can learn about the prison’s influence on the criminal justice system and hear tales about some of its most notorious inmates through exhibits and guided tours. The exhibit also looks at the evolution of initiatives to reform and rehabilitate prisons.
  6. Ossining Arts Council: Celebrate Local Artists – Be sure to check out the Ossining Arts Council if you enjoy the arts. This nonprofit company sponsors cultural activities and exhibitions that highlight the abilities of regional artists. The Ossining Arts Council provides a range of opportunities to engage with and support the arts in the Hudson Valley, from music and theater to painting and sculpture.
  7. Ossining Farmers Market: Stock up on Fresh Produce and Handmade Crafts – The Ossining Farmers Market is the ideal location to stock up on local merchants’ fresh vegetables, artisanal delicacies, and handmade goods. From May to December, this bustling outdoor market is open every Saturday from 8:30 am to 1 pm. You may find something for everyone among the dozens of sellers offering everything from farm-fresh eggs to homemade soaps.
  8. Ossining Boat and Canoe Club: Enjoy Water Sports on the Scenic Hudson River – The Ossining Boat and Canoe Club should not be missed by fans of water sports while visiting Ossining. On the beautiful Hudson River, this member-owned club provides sailing, canoeing, and kayaking. The club has activities for all skill levels, from rookie kayakers to seasoned sailors. The club is a terrific place to meet other people interested in water sports because it also conducts a range of social events and races throughout the year.
  9. Croton Point Park: Explore the Great Outdoors – Beautiful waterfront park Croton Point Park provides guests with a range of outdoor activities. Everyone can find an activity to enjoy in this park, from trekking and observing birds to having a picnic and camping. Year-round, the park serves as the venue for numerous cultural and environmental gatherings, such as the Clearwater Festival, complete with live tunes, cuisine, and environmental learning.
  10. The Jug Tavern of Sparta: Step Back in Time – Sparta’s Jug Tavern is a landmark bar that has been there since the late 1700s. With displays and memorabilia that highlight the history of the tavern and the community of Ossining, this historical site gives visitors a look into life in early America. A guided tour of the pub is available to guests, which includes a stroll through the beautifully renovated interior and a glance at the historical relics on display.

How To Get To Here

If you’re coming from New York City, you can take the Metro-North Hudson Line from Grand Central Terminal to the Ossining Station. The trip takes about 45 minutes and travels along the Hudson River. If you’re driving, you’ll access Route 9, which passes through Ossining, via the Saw Mill River Parkway or the Taconic State Parkway.

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Mia Shervington

Mia Shervington

Hey Westchester County, I’m Mia Shervington! I’ve had the incredible fortune to move to this amazing community, and I couldn’t imagine living anywhere else. I chose Peekskill as my home in 2001, and haven’t looked back! I’m a real estate agent with a passion for finding new places to explore in Westchester County. When I'm not selling homes, you can find me enjoying our local parks or taking in the sunset over the Hudson River. I'll never stop my quest for the perfect hot donut, despite what my waistline may say. Nothing is better than a fresh When I'm not snacking my way up the river, I also enjoy the trails at Teatown Reservation and the views over Long Island Sound at of Rye Playland (officially known now as Playland Park...whatever...LOL). I’m looking forward to connecting with you soon! See you around town! Mia Shervington | | (914) 407-3003 | NY#: 10401202023


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