Village of Ossining

The Village of Ossining, located on the eastern shore of the Hudson River 30 miles north of New York City, is one of a number of river towns with older industrial/waterfront and historic downtown areas. Ossining is approximately three square miles, has a population of about 26,000 and has three miles of waterfront along the Hudson River. It was incorporated as the Village of Sing Sing in 1813 but changed its name to Ossining in 1901.

Your Beyond-Perfect Day in Ossining:

Start with breakfast: Get your day going with a coffee at First Village; for a more leisurely start, try the all-day brunch menu at Tasty Table or all-day breakfast at DD’s Diner.

Stretch your legs: Hike the Croton Aqueduct Trail from Gerlach Park or stroll back in time with a self-guided Museum in the Streets heritage walking tour of downtown Ossining.

Stop for lunch: Go healthy at Good Choice Kitchen Vegan Café & Culinary Center or indulge in a pizza (you’ve earned it!) at Village Villarina’s.

Browse and buy: Catch the regularly changing art installations at Bethany Arts Community, then browse some of Ossining’s unique shops—you’ll find children’s gifts and toys at Penny & Ting and sustainable and fair trade home goods at Melita’s Home Furnishings.

An afternoon treat: Don’t miss the handmade small-batch ice cream at Bigfoot Creamery.

Watch the sunset: Pick a dinner spot with outdoor seating and a sunset view over the Hudson River—two great choices are 3 Westerly and The Boathouse. You can also watch the sunset from Sparta Park or Henry Gourdine Park, or from the river itself with a kayak rental.

Stay longer: Extend your getaway with a hotel stay.

The Village of Ossining has:

  • A diverse population
  • Breathtaking views of the water and pristine Hudson Palisades
  • A historic downtown
  • A public library that offers various cultural events to the community
  • The distinction of being voted “One of the Most Architecturally Beautiful Towns” by Westchester Magazine in 2012.
  • Teatown Lake Reservation: An environmental education center and nature preserve offering birds of prey, animal displays and extensive trails
  • Dale Cemetery: The final resting place of such historic figures as Civil War General Thomas Allcock; jazz guitarist Sonny Sharrock; and Samuel Youngs, the inspiration for the character Ichabod Crane in Washington Irving’s story, “The Legend of Sleepy Hollow.”
  • The Briarcliff-Peekskill Trailway: A 12-mile linear park that runs from the Town of Ossining north to Westchester County’s Blue Mountain Reservation in Peekskill.

For more information about Ossining, visit these sites: