Overview
Ossining is the name of both a village and a town in Westchester County in the state of New York in the United States of America.
3 sights · 9 things to do · 6 places to eat · 1 bars & cafés
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Ossining
Ossining Heritage Area
The Joseph G. Caputo Community Center of Ossining features wonderful exhibits for visitors to the historical area.
Sing Sing Prison Museum
he collection features a replica of the original electric chair and a collection of homemade knives confiscated from prisoners.
Ossining Arts Council Gallery
For art lovers, be sure to check out the monthly exhibits displayed in various locations throughout the community.
Ryder Park
Features a soccer/football, fitness trail, horseshoe pits, pavilions, tennis courts, basketball courts, ball fields, playground, picnic area, rest rooms.
Gerlach Park
Features horseshoe pits, pavilions, hiking/nature study, ball fields, playground, picnic area, rest rooms.
Veteran's Park
Features areas for soccer/football, horseshoe pits, fishing, bocce courts, basketball courts, ball fields, playground, picnic area, rest rooms, roller hockey rink.
Plan your trip
Best time to visit & weather
Most comfortable: May–Sep. Summer highs reach about 82°F; winter lows dip to about 21°F. Cold months (Jan, Feb, Dec) can bring snow and ice; check road conditions. Wettest: Sep and Mar. (climate data from nearby Briarcliff Manor)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- HPN Westchester County Airport, White Plains — 10 mi away. Directions
- TEB Teterboro Airport, Teterboro — 24 mi away. Directions
- LGA LaGuardia Airport, New York — 26 mi away (major hub). Directions
Traveling by car is the most convenient way to get around the town, as it also makes traveling to nearby locations more efficient. If you don't bring your own car, renting a car during a short-term stay may be helpful.
Full “Get in” guide ↓Budget & where to stay
- Typical meal: about $10 per person at listed restaurants.
Options are grouped as Budget, Mid-range, Splurge in the Sleep guide ↓.
Sample 3-day itinerary
Day 1
- Morning Ossining Heritage Area, Ryder Park
- Lunch New Yummy China Wok
- Afternoon Louis Engel Waterfront Park, Old Croton Aqueduct
- Dinner Lucy's Pizzeria
- Evening Karma Lounge
Day 2
- Morning Sing Sing Prison Museum, Gerlach Park
- Lunch The Boathouse
- Afternoon Buck Johnson Park, Ossining Village Fair
- Dinner Los Abuelos
Day 3
- Morning Ossining Arts Council Gallery, Veteran's Park
- Lunch Capri Pizza & Pasta
- Afternoon Cedar Lane Park, Farmers' market
- Dinner Ossining Pizzeria & Restaurant
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
There is an amazing variety of restaurants, with ethnic food geography ranging from Northern European (German and Swiss) to South American (Peruvian, Mexican) with stops at Portugal and Italy. Italian-American cuisine is particularly delightful.
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
The village of Ossining lies within the township of the same name. As one of the smaller towns within Westchester County, Ossining is well known for its humbling diverse character. The variety of cultures, ethnicities, and socioeconomics has created a town that offers a unique glimpse of America’s melting pot. Along the Hudson River (just north of the Tappan Zee Bridge) and 30 miles north of New York City, Ossining is a great destination for those looking for a taste of metropolitan life in a suburban setting.
Get in
By plane
- Westchester County Airport, 240 Airport Road, White Plains, +1 914 995-4860 (airlines). The closest airport, about a 30-minute drive. Rental cars are available.
- Stewart International Airport, 1180 First St, New Windsor, +1 845 564-2100. Another alternative to the congestion of the 3 major airports. Allegiant Air, American Eagle, and JetBlue operate flights from Florida and Philadelphia (Mar 2021).
- Newark Liberty International Airport, Newark, New Jersey, John F. Kennedy International Airport, and LaGuardia Airport: The three major international airports in the New York City area offer service to just about anywhere. Westchester-based taxi and livery cars offer regular service to and from the three internationals from most areas of the county. New York City yellow cabs will take to you Westchester in a pinch, but the fares can be exorbitant. If staying in Westchester, ask if your hotel offers shuttle service.
By car
Traveling by car is the most convenient way to get around the town, as it also makes traveling to nearby locations more efficient. If you don't bring your own car, renting a car during a short-term stay may be helpful.
By taxi
Whether you're going to the airport or coming home from a late-night dinner along the river, multiple taxi services are available for those who seek to travel distances unavailable by other means of transportation. Most taxi services charge $5 for intown destinations.
By train
Metro-North Railroad – Hudson Line. Express service between Ossining station and New York City's Grand Central Terminal is about 50 minutes. A one-way ticket costs $11.25 off-peak and $14.75 peak. Local service is available between other Metro-North commuter stations. Full weekday and weekend schedules are available online. Local taxis are usually on hand, and Zipcars are available at this station. On-board fares are subject to a stiff surcharge, so buy your tickets online or at the vending machines in the overpass across from the station building.
Long-distance connections with Amtrak are available in New York City's Penn Station and at Metro-North's Croton-Harmon station.
Go Ossining railway station
By boat
- Haverstraw–Ossining Ferry. 15 minute ferry trip across the Hudson River between Ossining and Haverstraw, NY, operating during weekday rush hours only. The one-way fare is $4.25 for adults and $2 for children (6-11) and seniors. Children 5 and under ride free. Operated by NY Waterway.
By bus
- Bee-Line System. Westchester County's bus service provides access to White Plains and other locations in the county. Schedules and route maps are available online and at the Ossining train station.
Get around
Route 9 is called Highland Avenue in Ossining (in adjacent villages it is usually named Broadway). Cars are the most efficient way to get around town, although one can take advantage of the taxi and bus services.
See
See Ossining Heritage Area
The Joseph G. Caputo Community Center of Ossining features wonderful exhibits for visitors to the historical area.
Do
Parks and gardens
With approx. 130 acres of land devoted to recreational use, there are a variety of beautiful parks for kids, and even adults, to enjoy.
Do Ryder Park
Features a soccer/football, fitness trail, horseshoe pits, pavilions, tennis courts, basketball courts, ball fields, playground, picnic area, rest rooms.
Do Gerlach Park
Features horseshoe pits, pavilions, hiking/nature study, ball fields, playground, picnic area, rest rooms.
Do Veteran's Park
Features areas for soccer/football, horseshoe pits, fishing, bocce courts, basketball courts, ball fields, playground, picnic area, rest rooms, roller hockey rink.
Do Louis Engel Waterfront Park
Located next to the Ossining railroad station, this riverside park features areas for fishing, playground, picnic area, a sunning beach, and rest rooms.
Do Buck Johnson Park
As one of the more quaint parks, Buck Johnson's has basketball courts and a playground.
Do Cedar Lane Park
Features fitness trail, basketball courts, fishing, picnic area, restrooms, soccer field. Membership to an open-door swimming pool can also be purchased for the summer season.
Do Old Croton Aqueduct
Go hiking or biking on the aqueduct's trailway. The original water supply to New York City is now a walking trail that runs from Croton-on-Hudson in the north to Yonkers in the south. Over the 180 years since it was built, portions have disappeared from the downtown areas of several river towns, including Ossining. Art Barn at 211 N. Highland Ave. sells maps of the trail.
Events
While one can find a variety of entertainment held throughout the year there are a few major annual events beloved by community members
Do Ossining Village Fair
Ever summer, the town closes down Main Street (located in the heart of Ossining) for must-attend festivities. For a small fee, businesses and organizations in Ossining can purchase booth spots along Main Street to promote their cause. They offer a variety of services for the public, from food to keychains to activities for kids. It's a perfect way to spend a summer day with friends and neighbors.
- St. Anne’s & St. Augustine’s Fairs Two of the largest Catholic Churches in the town hosts a carnival every June and August, respectively. The St. Anne's Fair and the St. Augustine's fair are great events for all ages, particularly families. Rides and games for kids (or those young at heart), great food, and even gambling for the adults bring together all members of the Ossining community.
Buy
Shop Arcadian Shopping Center
Stores include Stop-n-Shop supermarket, DSW Shoes, Verizon Store, and CV S pharmacy. Dining includes an Italian restaurant, a hibachi steakhouse, an ice cream parlour, McDonald's, and Subway.
Stores include A&P supermarket, a hair salon, pharmacy/boutique store, wine & liquor store, and Chase bank. Dining includes a pizzeria, Carvel, Subway, Baskin Robins, Dunkin' Donuts, and a Japanese restaurant.
Eat
There is an amazing variety of restaurants, with ethnic food geography ranging from Northern European (German and Swiss) to South American (Peruvian, Mexican) with stops at Portugal and Italy. Italian-American cuisine is particularly delightful.
Budget
Eat Lucy's Pizzeria
Great pizza and Italian dishes make this small pizzeria a local favorite. Selling items from individual slices to entrees.
Eat Ossining Pizzeria & Restaurant
Delivery, take-out, and sit-down Italian restaurant.
Eat New Yummy China Wok
Chinese cuisine. Take-out and delivery available.
Mid-range
Eat Los Abuelos
Mexican cuisine.
Eat Capri Pizza & Pasta
Sit-down Italian restaurant. Child friendly.
Splurge
Eat The Boathouse
Located along the Ossining waterfront, the locals come here for great American and seafood cuisine. Outdoor dining available.
Drink
Drink Karma Lounge
Martini bar and grill with international cuisine. Daily happy hour specials. Features a live band and late hours on Friday and Saturday nights.
Sleep
Budget
Mid-range
Splurge
Stay safe
Dial 911 from any telephone for emergency police, medical, and fire services.
Go next
For those seeking adventure outside of Ossining, the surrounding NY area features numerous destination spots suitable for all.
- New York City. Ossining is only 30 miles north of Manhattan, which makes it easy for anyone to travel to and from the Big Apple. For those not looking to splurge on a week-long urban adventure, day trips or even a special dinner excursion are simple and absolutely worth it! If you're worried about driving in the busy city, the MetroNorth train is a short 45-minute ride along the Hudson River.
- Woodbury Common Outlets. Located right across the Tappan Zee Bridge in Central Valley, NY, this incredible outlet center is a popular shopping haven for both New Yorkers and tourists from around the world. Stores range from casual to designer, such as Gap, Burberry, Polo, Disney, and many more. A food court and restaurants are also provided to keep shoppers on the move.
- Palisades Center Mall. Also located right across the Tappan Zee Bridge in West Nyack, NY is a massive 4-level shopping mall. A variety of retail stores for shoppers to explore, as well as an ice skating rink, movie theater, and fun zone for kids.
- Greater Westchester Area. Activities such as ice skating, miniature golf, concerts, theatrical performances and historical tours are all within driving distance in the county.
Nearby
Briarcliff Manor
City / town · 43 listings · 1 mi away
Croton-on-Hudson
City / town · 14 listings · 3 mi away
Pleasantville
City / town · 30 listings · 4 mi away
Sleepy Hollow
City / town · 23 listings · 5 mi away
Chappaqua
City / town · 12 listings · 5 mi away
Nyack
City / town · 8 listings · 6 mi away
Tarrytown
City / town · 34 listings · 6 mi away
New City
City / town · 2 listings · 7 mi away
My experience
Write about your trip here. Notes save automatically in this browser as you type; back them up from My journal.